Category Archives: Chicago

20×2 Chicago: “Are You Ready? – July 8th, 2023

Scott Smith at 20x2Chicago on July 8, 2023
Photo: James Allenspach

20×2 Chicago is a storytelling/performance series hosted by Andrew Huff. In it, 20 people answer one question in two minutes. This edition’s question was “Are You Ready?” and I was one of the 20 to answer it.

This show is deceptively difficult. Two minutes is no time at all to get across an idea or performance. Your piece has to be tight. More than once when writing something for 20×2, I’ve left funny bits or lines I love in the cut section of the doc because I needed the time back for stuff that was essential.

Many performers include some kind of visual element or audience participation. One time someone did a stage dive. On Saturday night, one of the pieces involved the entire audience trying to throw ping-pong balls into a bucket onstage and ended in Andrew doing a shot of tequila. I am not that clever so I wrote something and this is it.


This will only be two minutes but I’m going to give you the “too long, didn’t listen” version anyway. The answer is “no, but do it anyway.”

Are you ready? No, you never are. Not truly, not in the ways you think you need to be.

At best, you can name the thing. And if you can name the thing, you can know it, defeat it, or demonstrate superiority over it.

“Are you ready?” is the least helpful question in these moments. You may find yourself needing to ask yourself other questions. Like what’s next or what am I doing or what the fuck?

I don’t say this because I think you won’t fail. In fact, you will. Not in big ways, perhaps, but in small ones.

I’ve not been ready plenty of times.

At least twice in my life, I’ve had jobs I wasn’t ready for.

I was once in a marriage I wasn’t ready for.

These are some of the biggest failures one can experience.

But guess what? I did it anyway. And I’m still fucking here. You will be, too.

I’m 48 years old. Your mileage may vary but around 45 I entered my “don’t give a fuck” years.

Here’s what I do instead: Stay inquisitive. Be ready to learn something new. Get challenged. Defend the point of view you spent all this time honing. Hang on to what you’ve earned through experience.

This is not to say you shouldn’t keep your mind and heart open to the needs and concerns of others. This is not about ignoring other people, it’s about ignoring the you that doubts you, the you that worries if it’s not perfect, the you that tells you you aren’t ready.

That’s not your best self.

The one that does it anyway? That’s your best you.

The line between being ready vs. not ready is razor-thin. One moment you’re not, the next you are.

And that moment is now.

Photo: James Allenspach, Flickr

The intersection of the Dan Ryan and Chicago segregation

When I think about racism, segregation and the systems put in place to reinforce them, the Dan Ryan Expressway comes to mind. In part because of the complexity of it.

The Dan Ryan runs eleven miles, from 95th Street on the Far South Side to what’s now known as the Jane Byrne Interchange – the point where the Dan Ryan, the Eisenhower and the Kennedy meet.

As you drive north on the Dan Ryan, you see the skyscrapers of downtown rising up like Oz at the end of the yellow brick road. Fourteen lanes of traffic serve 300,000 people a day by one count. It’s either packed with cars during rush hour or, in off-peak times, Mario Kart come to life.

The Dan Ryan is not for the faint of heart or student drivers.

Growing up, the Dan Ryan was Chicago for me. A fearsome, muscular roadway that also sported a 75-foot-long, 40-foot high set of flashing red lips. Schools, businesses, and culture lined it. The Dan Ryan’s road signs tantalized with exciting places to visit if you took this exit or that one. Two versions of Comiskey Park, home of the Chicago White Sox, have towered over it at 35th Street.

American Pharoah notes the Dan Ryan Expressway was one of three expressway systems built under Mayor Richard J. Daley – the Stevenson and the Kennedy are the other two. Its construction was made possible through the Federal Aid Highway Act of 1956.

The book also argues that it reinforced what had up until then had been a historical dividing line between Black and white Chicago neighborhoods.

The original plans for the Dan Ryan called for it to cross the Chicago River almost directly north of Lowe Avenue, Daley’s own street, and then to jag several blocks, at which point it would turn again and proceed south. But when the final plans were announced the Dan Ryan had been “realigned” several blocks eastward so it would instead head south along Wentworth Avenue. It was a less direct route, and it required the road to make two sharp curves in a short space, but the new route turned the Dan Ryan into a classic barrier between the black and white south sides.

Langston Hughes was beaten up for crossing Wentworth Avenue, an unofficial dividing line between Chicago’s Black Belt and the white neighborhoods of the South Side. This included Bridgeport where Daley grew up. It was a line defended with violence by the Hamburg Athletic Club, of which Daley was a member in his youth, during the period of the 1919 race riots. “Athletic clubs” or “youth clubs” in this time were often covers for white gang activity or political power – or both.

The Dan Ryan’s 14 lanes of traffic would make it much harder to cross Wentworth Avenue by creating a significant obstacle in access to it from the east.

Pharoah also notes the construction of the Dan Ryan was announced less than a month after the City Council approved the building of the Robert Taylor Homes. The Robert Taylor project would be built in the State Street Corridor where other large public housing was already located: the Harold Ickes Homes, Dearborn Homes, and Stateway Gardens.

The overwhelming majority of the people in these communities were Black and lacked access to higher-income jobs, in large part because of the warehousing approach Chicago and other large cities used to provide housing that clustered Black people in parts of the city that separated them from white people.

The State Street housing projects, almost all of which are now long gone, were located just east of the Dan Ryan, which was just east of Wentworth Avenue. The violence that occurred in the 1919 riots, often from whites going into Black neighborhoods, was concentrated in a few places, particularly along State Street, decades before the Dan Ryan was contemplated.

The construction of the Dan Ryan in close proximity to the housing projects of the South Side did not increase the access of their residents to the opportunities of jobs, commerce, and attractions. If anything, it reinforced the lack of access. A 1998 New York Times article quotes one resident of the Robert Taylor Homes describing the projects as a “public aid penitentiary.”

It’s hard to find a more obvious metaphor for Chicago segregation. But the way the story plays out is more complicated than it would seem.

The racial makeup of many South Side neighborhoods changed significantly in the years following the construction of the Dan Ryan with many previously white neighborhoods becoming majority Black. According to a June 2020 report from the Chicago Metropolitan Agency for Planning, Bridgeport itself is now 39% Asian, 33% white, 23% Latino, and 2% Black.

As a WBEZ Curious City segment points out, the Dan Ryan didn’t create the segregation in this part of the city. The story notes author Dominic Pacyga’s Chicago: A Biography says that “political power, street gangs, railroad viaducts, and railyards — posed greater obstacles to blacks’ expansion into white neighborhoods.”

Another source in this piece says the Dan Ryan “helped expedite the exodus of the white community from the Southwest Side.”

It’s an inescapable fact that Chicago’s built environment often reinforced or exacerbated segregation. And that’s before you get into the history of redlining and other ways in which racism and real estate intersected.

For instance, in the map for the WBEZ segment, the proposed and final routes of the Dan Ryan are shown. The final route meant more Black-owned homes that white homes would be eliminated to make way for the expressway.

When you consider how Black families have more of their assets and wealth concentrated in their homes than white families you see the institutional effects of racism are often complex and indirect.

Now, none of us built the Dan Ryan Expressway; it opened in 1961 – years before many of us were born. We weren’t consulted about the route. But the 300,00 people who use it each day benefit from its convenience and speed. We can’t ignore that.

Should we tear up the Dan Ryan Expressway and rebuild it completely? No. Nobody’s arguing that.

We should still recognize that the construction of it reinforced a desire on the part of those who built it to keep Black people and white people separated.

Besides, it’s not like the use of the Dan Ryan Expressway is killing black motorists at a higher rate than white motorists.

Or the tools and training given to the staff of the Illinois Department of Transportation put them in a position where they have to choose between their lives or the people using the road.

Or we have to hold fundraisers because we aren’t equipping them with enough fluorescent vests to wear when they are in harm’s way.

Or the people who work at IDOT are committing suicide at a higher rate than the national average.

If that were happening, we’d definitely need to think about a complete rebuild because it’s harming everyone involved.

Chance The Rapper Buys Chicagoist

What will Chance The Rapper’s Chicagoist become?

Chance The Rapper Buys Chicagoist

(Disclosure: I was a writer and editor with Chicagoist from 2004 to 2007 and stayed in close communication with people who worked there up until the time it was sold to DNAinfo. While some of the below is based on knowledge gleaned during that time, none of this is based on off-the-record conversations. For my full ethics disclosure statement, read this.)

Last week, Chance the Rapper announced he’d purchased Chicagoist, a website which covers Chicago news and culture, from WNYC, which bought it from DNAInfo/Gothamist after the local news sites were shut down in the wake of a unionization effort.

Why? And what’s next?

Owning the medium to own the message?

A brief announcement about the sale divulged little about Chance’s plans, but lyrics in a simultaneously released song called “I Might Need Security” perhaps shed some light on his intentions:

I missed a Crain’s interview, they tried leaking my addy
I donate to the schools next, they call me a deadbeat daddy
The Sun-Times gettin’ that Rauner business
I got a hit-list so long I don’t know how to finish
I bought the Chicagoist just to run you racist bitches out of business

Genius can give you the background on the media beefs above and the Chicago Reader’s Leor Galil goes deeper into the issues between Chicago media and Chicago hip-hop.

Of greater concern for Chance’s new venture is the moment last year when Chance pressured MTV News to remove an essay from its website that he and his manager Pat Corcoran “both agreed that the article was offensive,” in Corcoran’s words.

Suffice it to say Chance keeps the media at arm’s length and has been savvy about managing his image, going all the way back to 2013 in this Chicago magazine piece from Jessica Hopper (who coincidentally was MTV News’s editorial director last year):

Chance the Rapper doesn’t want to show me his hood. The burgeoning hip-hop star sits in my car behind the Harold Washington Library issuing a flurry of excuses: It’s too hot. Chatham, the South Side neighborhood where he grew up and filmed his viral video “Hey Ma” (it’s on YouTube), is too far. He has to be at the studio in an hour. Anyway, that place isn’t really his story, he insists. His story is “here,” he says, motioning toward the library.

On one hand, you could imagine Chance is tired of being misrepresented by “the media” and like other savvy cultural creators he’s taken the means of production into his hands to exert more control over his image. The MTV News blow-up, the “Security” lyrics and the Chicago magazine excerpt all lend some credence to this theory.

Also of note is Corcoran’s $15,000 founding member donation to Block Club Chicago, the new hyperlocal Chicago news organization (disclosure: I am also a member of BCC but at 1% of that amount). Considering Chance’s philanthropic endeavors and he and Corcoran’s recent interactions with journalism it’s tough to know whether this is more in line with the former or an attempt to hedge bets on the latter.

To be taken seriously as a funder of independent journalism, he’ll need to address the questions around all of the above. But if I had to guess, I’d imagine he’ll be a media owner more in the mold of a Mansueto or Bezos than an Adelson.

Chance has been an undeniable force for good in Chicago culture. The erstwhile Chancellor Jonathan Bennett is the son of politically active parents whose lives have been devoted to public service. He is seemingly a devoted father, philanthropist and community advocate who has donated upwards of two million dollars to Chicago’s public schools, testified at the Chicago City Council and supported voter registration efforts. When we talk about a music community, it looks a lot like what Chance creates in Chicago by investing in its people.

Chance’s familiar critique of mass media is that it too often misses nuance in favor of an easy-to-swallow narratives and elevates conflict over conversation. Buying Chicagoist could be a way to put create another independent media organization in Chicago, albeit one run by a well-heeled single investor, that serves as a catalyst for the kind of social change he’s been creating.

A business plan for a business, man

Mike Fourcher, a former Chicagoist colleague and also the former publisher of a few hyperlocal news and politics sites, delves into the business and audience side of things in this post. In short, re-building Chicagoist won’t be easy. The business model it had as part of the Gothamist network is lost as a standalone site. With an increasingly mobile audience accessing news via phones, local news sites are competing for attention with not just national publications but also everything that’s in app form whether it’s Facebook, Netflix, Fortnite or text threads.

But with this sale, Chance and Chicagoist will have some valuable assets most startups don’t. When it was shut down, Chicagoist had a sizable social media audience of 500,000 across Facebook, Twitter and Instagram, monthly unique visitors of 700,000 and an email list of 29,000 subscribers. All that’s waiting to be reactivated.

One possible way for Chicagoist to start re-engaging and building on its previous audience is to act as an amplifier/partner of news from the startups who cover underserved-by-news neighborhoods still trying to get to Chicagoist’s size like City Bureau and The Triibe Chicago. This isn’t about aggregating the work of others, but using Chicagoist’s already existing audience to support community engagement.

Going back to Mike’s post, he ends it this way:

Maybe Mr. Bennett wants to turn Chicagoist into a kind of “Players Tribune” for entertainers. Maybe he’d like to use the title as platform for something other than news. Perhaps he is thinking of creating a site about the experience of Black Chicago, a sorely under-reported topic. “Chicagoist” could mean so many things. We shouldn’t limit ourselves to what it’s meant in the past.

All of which leads to one a couple key questions: What is Chicagoist’s voice going to become and what does its audience need and want?

I have a few thoughts on how to answer that.

What could Chicagoist be?

If he has the time, team and treasure to invest, Chance’s Chicagoist could be an exploration of, and a check on, emerging power in Chicago: who has it, how they use it and what are the ways that power affects the everyday lives of Chicagoans, particularly those on the South and West sides who often find a surge of interest in their concerns when something goes wrong, but not as often when something goes right. How is power being used for good as well as for destruction?

It shouldn’t be another variation on “watchdog” reporting though. It can, and should, be celebratory. Imagine this article as an ongoing content vertical with products and events built around it. Billy Penn is already doing something like this with Who’s Next in food, music, the law, education, schools, etc. Someone else will try it here if Chance/Chicagoist doesn’t.

Crain’s Chicago Business covers established power with a specific downtown focus and a high-income audience. Daily papers do this for politics and big business. Local publications cover some of this in a breaking-news, scoop-driven way. But it’s rare to see, for example, a deep dive into the history of a longtime neighborhood developer building condos with first-floor retail in a neighborhood that isn’t on a “hot” list. Not to mention those just coming up.

There’s also something to be said about being a voice for those whose views often go underrepresented in this city. Chicagoist could be the source that represents Pilsen and Humboldt Park and Jackson Park in the way that the Tribune represents…well, often, the western suburbs, bridging the gap between young progressives and older, passionate Chicagoans. It’ll mean taking stands, reflecting the grit of the city, avoiding both the middle ground and “both sides” reporting – pointing out truth, lies and agendas.

This kind of voice would mean elevating people on the front lines of these community issues, making sure the audience sees itself reflected in what’s discussed and giving the readers a stake in it, which increases relevancy, word of mouth and audience size.

We see these voices all over social media. They are guiding the conversation and too often the traditional news media products are playing catch-up to them or just throwing up a screenshot without delving into context. They should be a part of what Chicagoist does, even if, or perhaps especially if, it doesn’t involve traditional journalists.

While the Tribune seems to have cornered the market on op-eds by people who are leaving Chicago and Illinois, Chicagoist has an opportunity to talk about why people stay here and build. Young entrepreneurs who have never set foot in 1871 are creating businesses here. The national political organization Run for Something had an event here last year that was even larger than one in D.C. Who attended, why are they running? Can we track their campaigns in a way that is shows the path and doesn’t follow the patterns of who’s-winning-who’s-losing, horse-race journalism?

When we do this, we find:

  • The next lead-contaminated pipes before they harm the brains of our kids and make them more susceptible to violence
  • The next models for entrepreneurship in neighborhoods which others can replicate and build a hyperlocal economy
  • The next political movement leaders
  • The next…Chance the Rapper

It’s about giving the audience an understanding of power and how it’s used but also in reinvigorating the trust between reader and publisher by demonstrating that we’re listening to what they need, not just telling them what we think they need. Hearken, a Chicago startup with national reach, has been pioneering this approach. I’m surprised more newsrooms aren’t using their tech and process. Also, City Bureau’s public newsroom collaborations have showed that developing news products side-by-side with readers has tremendous value for the end product and develops audience loyalty.

This starts with research on not just on the previous Chicagoist audience, but also its potential readers – the ones who stepped away from Chicagoist and the ones it never appealed to – as well as the places they live. The geographic communities and the psychographic communities – their interests and needs. What do they need out of a media publisher vs. a mobile website vs. an email product vs. a social feed vs. ongoing coverage of a topic that’s created for the place in which it appears.

But more importantly, it allows Chicagoist to own the relationship with its readers and reinvigorate the entire model of useful products and information given to readers in exchange for trust, money and information about themselves. It takes work, but it’s how you develop a true business model.

It also makes the content actionable for the audience. For someone with Chance’s philanthropic leanings, a media organization that consistently says “If this is important to you, here’s what you can do…” could be an important next step.

Correction: A previous version of this article listed Pat Corcoran’s Block Club Chicago contribution as $10,000 based on this page. Block Club Chicago Director of Strategy Jen Sabella says the actual amount was $15,000 and said that “Pat’s contribution to BCC was not on behalf of Chance…he just liked/missed his neighborhood news and wanted to help us get going again.”

Image of Chance the Rapper by Flickr user Julio Enriquez licensed through Creative Commons

A guide to yesterday’s Chicago protests on the Dan Ryan – for people who are new to all this (and trolls)

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I spent most of yesterday watching reactions to the shutdown of the Dan Ryan to protest violence in Chicago.

Some of the reactions were genuine – people trying to come to a better understanding of why protestors chose this tactic and why it’s effective.

Some of them were super troll-y.

This is for both groups.

What’s the point of disrupting traffic on the Dan Ryan? Most of the people affected aren’t the ones causing the violence.

One of the biggest problems with addressing violence in Chicago is that it is seen as a problem isolated to a particular area and only affecting certain people and neighborhoods. Yesterday’s protest was like throwing a stone in a pond and causing ripple effects.

If you ended up talking about this protest and the issues surrounding it this weekend, that was the point of the protest. Shutting down the Dan Ryan makes that possible in ways other tactics don’t.

Without calling more people into this fight, the problem doesn’t get solved. Without more pressure on the mayor, the governor, the City Council, it doesn’t get solved. Without a broad-based coalition of people from around the metro area who demand solutions, it doesn’t get solved. Shutting down the Dan Ryan made the problem impossible to ignore.

It was also about forcing people who access Chicago via the Dan Ryan to see parts of the city they otherwise are able to avoid. If you wanted to access the city via I-57, you got diverted to 95th or 103rd Street. You’d have to take State Street or Vincennes or any of the other streets that run parallel to the Dan Ryan to get into the city. You’d have to see the people, the businesses and neighborhoods that make up the South Side – all the places that are largely invisible if you’re taking the Dan Ryan.

At a minimum, this makes the problem more present, less a thing you hear about and more a thing that exists in real ways.

Why don’t they disrupt the spots where the drug dealers / gang members hang out?

People do this all the time. This article is from 2016, but trust me this kind of thing happens out of the reach of TV cameras and reporters frequently.

In fact, Father Pfleger himself leads marches like this every Friday night. His church, St. Sabina, also has an ongoing violence intervention program.

Bringing more attention to the people doing this work is also what the protest was about, not to mention talking about issues like low wages, schools, jobs, etc.

So why don’t they protest in front of the mayor/governor/Mike Madigan’s house?

People do protest in front of the mayor’s house. Often enough that it doesn’t create the kind of disruption or visibility that something like this did. But honestly, this is like asking why civil rights protestors walked from Selma to Montgomery or blocked the Edmund Pettus Bridge. There’s a tendency with protests to see them as either/or rather than “yes, and…”

This is just politics! It’s just a publicity stunt.

Yes. You’ve captured the exact reason why protests happen: to publicize issues and put pressure on political decision makers.

But I’ll agree with you on one point: The posturing by the mayor and the governor yesterday was not particularly insightful or helpful. Especially when you consider the mayor and the governor have both tried to crush unions and teachers, two groups that provide economic and educational health to the affected communities.

This just creates a lot of chaos for law enforcement.

It definitely requires a significant deployment of resources. I don’t have the exact numbers, but I’ll bet it’s roughly equal to the time we closed down Michigan Avenue and most of downtown when the Blackhawks won.

We close streets, disrupt traffic and re-deploy law enforcement officers all the time for street fests, parades, etc. It affects people who aren’t participating in those events, too. I’m not saying we shouldn’t have those things. We should! But again it’s “yes, and…”

It’s a question of what we prioritize.

Also, you might have missed Chicago Police Superintendent Eddie Johnson marching arm-in-arm with Father Pfleger down the Dan Ryan. Was this more politics? Maybe. But most folks think better relations between the community and law enforcement are what’s needed here. So if this brought those groups together in a way that showed unity? That’s probably helpful.

Do you think people really don’t know about violence in Chicago?

I think most people hear about Chicago violence, but they don’t know much about it.

Do they hear it exists? Sure. Do they know why it happens? The real root causes of it and not just the stuff Hannity and his ilk spout? I don’t know.

Do they know the ways we fought gangs and dismantled public housing led to a less centralized, more violent gang problem?

Do they know we closed down mental health clinics in our neighborhoods which meant it was more likely that we are trying to treat medical issues as law enforcement problems? And that Illinois’s ongoing budget issues closed even more?

Do they know we closed 40+ schools in black and brown neighborhoods which meant their education was disrupted or kids had to cross gang boundaries? Do they know you end up gang-affiliated not by choice but by location?

Do they know the manufacturing and industrial jobs that were a large part of the South Side haven’t been replaced and that people there are (ahem) economically insecure?

People who live in this city – anywhere, from the North Side to the South Side to downtown and elsewhere – have a part to play. In part because resources to deal with the issue often flow to what demographer Rob Paral calls “the zone of affluence” which stretches from downtown to as far north as Lakeview and parts beyond. If you live in the suburbs, you benefit from the metro area being an economic powerhouse, not to mention the times you come into the city to enjoy its attractions and culture. Yesterday’s protest was about reaching you, too, and asking for your help.

I also find it interesting that some of the same people who say “What about Chicago?” whenever there’s a protest over a mass shooting at a school, church, movie theater, concert, etc. – to suggest no one is protesting over the violence here – are the same ones who are quick to decry this effort as well.

In order for all of us to be better educated on this topic, we need to seek out media, not just expect that it will reach us. More often than not, it’s in seeking out books, magazines and podcasts over TV, daily news and tweets.

It’s how we will know about Chicago violence and not just hear about it.

Why don’t these protestors spend their time calling for mandatory minimums or truth in sentencing laws?

Increasing the carceral state is a further drain on an already financially taxed system. Not to mention that mandatory minimums are usually implemented in ways that are racist and unequal. And Illinois already has truth-in-sentencing laws.

But if we’re interested in solutions that do more than warehousing people, we could start with restoring the funding to social service programs that try to interrupt violence in Chicago communities or provide jobs and other community services. Or we could work on re-opening mental health clinics. Or equally fund our schools.

Is a protest really going to solve this problem though?

By itself? No. And not even Fr. Pfleger thinks that.

We came out here to do one thing: to shut it down,” Pfleger said. “We came here to get their attention. Hopefully we got their attention. … Today was the attention-getter, but now comes the action.”

I’m going to put on my marketing hat for a second and suggest protests like this are about bringing in new participants through awareness and education. None of the other options above would have as much impact on awareness as what happened yesterday. It’s also important to talk through these issues and what else is being done to solve the problem so people know where/how they can spend their time and why it’s so vitally important.

Are the issues and their solutions complicated? Very much so. Chicago Tribune reporter Peter Nickeas talked yesterday about how the work that follows is about offering basic help and services to the people most likely to end up touched by violence:

Softball on Monday + Thursday, afternoon basketball, Tuesday night prayer group, twice-monthly tattoo removal, after-school probation programming w/ substance abuse, therapy, life skill classes, little league baseball. And of course, street outreach, violence intervention…they’ve done *tons* of work off the efforts of volunteers alone over the years, they still do. And people donate space, food, etc. But yea, things cost $. Space, vans, insurance, salaries, permits, jerseys and uniforms, etc.

Pete’s article from last year on how this work is being done in Little Village is a must-read on the topic.

So what am I supposed to do? I want to help, but I don’t know where to start.

Continue to ask questions and listen to the answers from people who’ve been doing this work.

For a regular deep dive into these issues, follow the coverage at WBEZ, Chicago Reader, City Bureau, South Side Weekly and Chicago Reporter as they often go beyond a daily news reporting model. This isn’t to say reporters at the Chicago Tribune and Sun-Times aren’t ever doing so, but the approach is different. Having said that, the long reads and watchdog reporting from both those papers (like Pete’s article linked above) are worth your time. Again, “yes, and…” not either/or.

Here’s a list of social service agencies that could use your time, talent or treasure. You could also learn more about the places that fly under the radar who are trying to help.

If each of us takes a piece of this, the load becomes a little lighter.

Image via Wikimedia Commons

Hugh Hefner: Janus in voluptatem

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I worked at Playboy for a year or so. I’ve written about it before, but it was filled with some of the best professional experiences of my life even though parts of it were the worst. (Shout-out to everyone in Playboy’s legal department for the time they sent me a cease-and-desist letter for talking to a reporter after they fired me.)

Turning this around in my head and reading some of the early comments on Hugh Hefner’s death, it occurred to me that what’s most striking about his life was its pronounced dichotomy.

The same man who championed sexual freedom as well as equal rights for POC, women and LGBT folk also reinforced misogyny, unrealistic standards of beauty centered on whiteness and a consumerist approach to living. When he advocated liberation for women, he did so to position them as “entertainment for men.” In all these ways, he was the best and worst of American idealism.

He simultaneously derided Midwestern values as he built a media empire in Chicago before abandoning it for a L.A.-based cocooned fantasy world. His was a family business, which his son and daughter both led, at different times, that occasionally preached contempt for the embrace of 2.5 kids and a picket fence. He imagined himself the picture of urbanity then built professional and personal worlds that never required him to leave the house.

He gave generously to support freedom of the press, public education and other worldly concerns, but lived a life of self-centeredness.

Hugh Hefner was a man of contradictions. Anyone who claims he was any one thing without acknowledging the other is not telling the whole story.

A conversation about leaving Chicago

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You saw this thing, right?

Whassat?

This thing where the kid from San Francisco talks about leaving Chicago?

If he’s from San Francisco how iz he in Chicago?

He moved here three years ago and it didn’t work out so he’s moving again.

Wait, he only moved ‘ere three years ago and he’s leaving already?

Well it didn’t work out for him.

So he’s black, huh? Lived on da West Side?

What? Why would you say that?

I mean, if he moved here tree years ago and he’s already leaving it musta been pretty rough. And if ya pay attention to all duh eggheads like I do then ya’d know da people havin’ da hardest time right now are blacks, especially on the Sout’ and West Sides. Dat’s who’s leaving town what with all the schools and clinics closed and da jobs lost and da violence and what not.

Oh. No, he’s not black. He’s white. And it sounds like he lives on the North Side.

Get outta here. White guys from da Nort’ Side don’t have problems.

He said he didn’t like the food and the beer is too expensive and he had a hard time dating.

Like I said. You know what’s expensive here? Housing.

Housing?

Yeah. It’s like 12 hundred a month for da average person. And then da minute somebody tries to bring in some actual affordable housing and make things livable like dat guy up in da 45th ward who’s trying to help vets then everybody starts screaming “Section 8! Section 8!” and other racist crap like we don’t know what dere talkin’ about, you know? Dese people wouldn’t know a Section 8 anything if a damn CHA building fell on ’em. What else does he say?

He says we’re not “sex-positive.”

We’re not what?

Sex-positive.

Buddy, I’m telling ya this guy never lived here. Ask any-a dese guys in dis bar and they’ll tell ya they are pos-i-tive-ly going to have sex tonight. They’re wrong, but dere pretty positive about it.

No, he means Chicago just has traditional views of gender and relationships and…

Oh and how did dis genius dat lived here for five minutes decide dat?

Apparently a table full of women thought he came off like a real jerk. He interrupted their evening and then he got mad when they didn’t want to talk to him.

Where was dis?

From what I hear, it happened at Estelle’s.

OK, well dat’s his first problem right dere. Nobody goes to Estelle’s to date. It sounds like dis guy thinks Chicago isn’t sex-positive because everyone here is positive dey don’t want to have sex with him and I don’t blame them.

He has some good points though.

Oh yeah? Like what?

Well he says it’s cold, we’re prideful and the CTA is kinda bad.

Stipulated.

And we’re kind of insular and a little on the conservative side.

He said that was a good thing, right?

No, he said that’s bad.

See, dis guy never lived in Chicago. Maybe he spent time here but he didn’t live here. Yeah it’s hard to break in here sometimes and people are kinda standoffish at first but that keeps out the dicks. Like guys who move here from San Francisco and expect Chicago ta worship dem because dere talkin’ about how sex-positive dey are.

I think he’s raising some things worth talking about though. We’re way too boosterish. We never talk about the problems of this city.

Excuse me, but dat is horseshit. Fire on da Prairie, Da Third Coast, Da South Side, Division Street, Boss. Alla dose books will gladly tell you what’s wrong with Chicago and dere right. But nonna dem are gonna say Chicago’s problems are because you can’t get laid or da beer’s too expensive.

Fair enough.

So where’s he moving to?

New York.

Wait, his complaints are that everything is too expensive and dating is hard and the transit sucks so he’s moving to New York?

Yeah.

Well good luck to him. Ask the bartender to put da Bears game on, wouldya?

With apologies to Mike Royko and Slats Grobnik

Photo by Flickr user Kylio licensed via Creative Commons

A few musings on why DNAInfo bought the Gothamist network

Today DNAInfo announced it is buying the Gothamist network. Why? Well here are a few thoughts.

(Full disclosure: I used to be a Chicagoist editor though it’s been a while since I’ve had any inside info on what goes on there. And I’m friendly with people at DNA but, again, I have no inside info on this deal and haven’t talked to anyone there about it. I’m merely an outside observer with a lot of time spent observing and working in Chicago media.)

First, this solves DNA’s need for more audience and Chicagoist’s need for content. DNAInfo New York has 2.5 million uniques, 108K newsletter subscribers and a combined social audience of about 160K though some of all of those numbers are duplicative, obviously.

But I think Chicago is the key to this sale. DNAInfo Chicago has about 1.8 million uniques, 168K newsletter subscribers and a combined social audience of 200K. Again, some duplication there. Chicago is DNA’s only other city site and has a larger email and social audience than NYC.

I’m not sure if the Gothamist figures here are rolled up or not, but I think it’s safe to say they are. So that’s 8M uniques across all their cities (including LA, DC, etc.), 846K of which are in Chicago.

The deal terms weren’t announced, but if Politico is to be believed and the deal is in the low seven figures, even with audience duplication you’re talking about significantly less than a dollar per user acquisition, not to mention DNA’s new footprint it all the -Ist cities. This was a bargain just in terms of numbers.

Again, you assume some duplication there but DNAInfo and Gothamist are all trying to own the very localized, neighborhood-focused stories. So either way you look at it, each network is going after the same type of reader though -Ist skews younger and DNA with a higher HHI.

But look also at the mission of the two companies and what’s been happening competitively in Chicago.

With ProPublica IL’s impending launch and Billy Penn’s rumored Chicago entry, there’s more competition in Chicago for local news eyeballs and DNA needed to shore up its presence here. Buying Chicagoist was an easy way to do that.

And, again, the types of stories DNA does well used to be the -Ist sites bread and butter (as well as Huffington Post Chicago’s local outpost which has since shuttered). -Ists aggregated DNA and both companies chipped away at each other. I don’t know what it means to be “DNA’s official blog” as it says in the announcement but I’d guess it means DNA can get aggregation eyeballs without damaging the strong reporting of the DNA brand. And it grabs back the lost audience that would read -Ist aggregation of DNA stories but not click through.

Gothamist has been trying to get bought for at least seven years now. Ricketts’ politics aside, ownership by a company who believes in local news is a much better ending than Kabletown.

If I was going to produce a Chicago news show, here’s what it would look like

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A little over a year ago, I was reading The Third Coast. The book is full of stories of how Chicago was a hub of innovation. Not innovation in the way we currently think of it – as “the Uber of X” – but innovation in poetry, architecture, television, print, music, business, etc.

The television and media part stuck with me. I hadn’t ever really understood what Dave Garroway did and how Studs Terkel’s worldview was given life through the medium of TV and how important it all was before this book.

It seemed like TV – or something akin to TV with a heavy social media component – could still do that. To take the idea of the Chicago school of experimentation and apply it to conversations we’re having now. What is Chicago’s place in the national conversation? Or why isn’t it more prominent in that discussion? And what can we do to change that through media?

So I asked the question “What’s missing from Chicago media?” As you can see from that link, I had a lot of help answering that question.

All those answers informed the below: a way to tell national stories through a Chicago lens.

I have no agenda in posting this now other than it was an idea I spent some time on and the results of it have never been published. And I wanted to get it out there before the ideas around it seem too old. Since I started the discussion it public, it feels right to continue it that way.

There’s so much I love about Chicago media. So many reporters and producers are doing vital work. We need more of it. We need to know how to pay for it, too. But I wanted to know what we could do that’s different.

This is that.

What is this show?
This show will look at what’s going on in the U.S. through personal stories based in Chicago.

But it’s a daily news and information show combined with advocacy. It delves deep into a single topic each day across TV and social and shows both how it affects the audience and what they (or others) can do to contribute to a solution.

In doing so, it answers three questions for the audience:

* What do we know?
* What do we think?
* What are we doing?

We do this by making sure the audience sees itself reflected in what’s happening on-screen and giving the viewers a stake in it, which increases relvancy, word of mouth and audience size.

This should not be driven by media talking heads or “experts.” Sure, there’s some of that in the “what do we know” portions but we should hear more from the people living the issues we’re exploring.

Most importantly, this will solve for the biggest problem viewers under 40 have with these kinds of shows: understanding how it affects them in their daily lives and what to do with this information in order to make a difference.

Why does this show need to exist?
There’s a need for a daily news/information show that goes deep into a topic and isn’t ruled by a “news peg” or the 24 hour cycle. Look at the response to Last Week Tonight with John Oliver. That show is revelatory because it exists outside the regular news cycle and motivates the audience to act.

There’s also a need to treat culture, food and arts with the same rigor and conversation as politics.

And we are perfectly positioned do all this here.

Chicago is a microcosm of the country, good and bad – in a way that NYC and LA can never be – while still remaining a national influence thanks to its geography and demographics.

Consider:
* Our struggles between public vs. charter schools
* The crime problems, whether in the “inner-city” or the suburbs and their drug problems
* A world-class mix of fine dining and street food has helped turn us all into foodies
* Neighborhoods that all have their own personalities, adding up to a larger whole  
* Arts and culture that’s the home of Lollapalooza, Pitchfork, the Goodman Theatre or the next Wilco

The subtitle of the book The Third Coast says “Chicago built the American dream.” We were and still are a great testing ground for ideas. In many ways, Chicago’s problems and successes still explain what’s going on in the rest of the country.

The knock on younger news audiences is that they are uninterested in news. This isn’t true. News is important to them.

What they dislike is how most news is structured: it features the same old players in the he said/she format and doesn’t demonstrate how it’s relevant to them. They get their news through social so their news needs to be inherently social.

“Simply put, social media is no longer simply social,” the Media Insight Project report says. “It long ago stopped being just a way to stay in touch with friends. It has become a way of being connected to the world generally — to send messages, follow channels of interest, get news, share news, talk about it, be entertained, stay in touch, and to check in and see what’s new in the world.”

We also need a show that explores a broad range of viewpoints. The second part of this post on Medium lists recommendations for news from a still-relevant 2002 study on youth (consider that this cohort now makes up part of the older millennial segment):

“Let youth speak for themselves.” “Highlight root causes and trends.” “Examine solutions other than increased punishment and incarceration.” “Link social problems to public policy.”

Right now, some news organizations – mostly national – do parts of this. But no one does all of it and especially not in video or live TV.

WBEZ’s public radio programming often does deep dives with community voices. Chicago magazine, DNA Info Chicago and Belt magazine do mixes of long features and personal stories that explore topics outside of news cycles. Some TV stations will do special reports like this – think Fox 32’s “Chicago at the Tipping Point” series. This format could mix all of these approaches in a much more exciting way.

What is it like? What makes it new/different?
We’d see two co-hosts, preferably late 20s/early 30s. To be demographically specific, the relevance of this kind of show would be increased with at least one person of color and a woman (two women of color would be ideal). They’re our guides, but they’re us: they’re asking questions, they’re asking for more detail, they’re exploring. They are not approaching this as the all-knowing journalist who keeps an arm’s length from the topic. But they have expertise and experience. More importantly, they’re entertaining. They approach these topics with humor, when appropriate, but can handle serious topics, too.

Also, there are three things about this that make it new/different:

Socially-sourced: The 13-week editorial calendar will be planned out in advance and posted online for viewers to see. Viewers will be encouraged to email/tweet/message us who they’d like to see on the show. This will help us ensure we’re not getting the same voices we always see in these types of shows and showcase more of the people who are affected by or living these issues.

Socially-driven: In addition to the video conversations, we’ll see curated tweets, FB posts and photos pop up live throughout the show. Viewers will be told how they can contribute to the conversation through an onscreen hashtag. (Yes, this kind of thing has been done before but it’s rarely relevant to what’s happening onscreen, it’s usually just noise).

Socially-relevant: Even though we’ll have planned our topics in advance, the social conversation will keep it fresh and of that day.

Here’s a rough outline of how this might work as an hourlong version (weekly) or a half-hour long version (daily). Keep in mind we discuss a single topic throughout the hour.

FULL HOUR

Segment 1: WHAT WE KNOW (11 minutes)
A mix of of host-led explainers with infographics and animation that introduces the topic. Provides context for the discussion to follow. Consider this like watching a live version of your favorite blog – maybe Andrew Sullivan’s The Dish in its time or one of the better Vox videos.

Segment 2: SKYPE INTERVIEWS / LIVE VIDEO CHAT – “WHAT WE THINK” (8 minutes)
From the social conversation we’ve seen before, we’ll choose some people to speak with live via Google Hangout, Skype or similar video setup. We’ll either do this one-on-one or in groups. This will help guide the conversation in the roundtable to come.

Segment 3: ROUNDTABLE INTRO – “WHAT WE THINK” (4 minutes)
Short profiles of the people we will meet in the intro. Who they are, what their background is, why we’re speaking to them. Quick thoughts from them on this conversation before we cut to break. We could do this live in-studio or – more ambitiously – as pre-recorded pieces that morning that are edited into the show. These should be people who have a stake in living with these issues, not people from think tanks or the heads of NGOs. Think block club captains, rather than aldermen.

Segment 4: ROUNDTABLE – “WHAT WE THINK” (11 minutes)
Our guests talk with the hosts about the topic. Conversational, open, not argumentative. This will be interspersed with social posts in the lower-thirds. Some of the social conversation will be used as the basis for discussion.

Segment 5: WHAT WE’RE DOING (8 minutes)
Conversation about people and places that are working on solving the problems we’ve discussed. Specific information about how the viewer can participate.

This could include more live Skype video interviews and/or an in-studio interview with a person who works at a social service, agency, a neighborhood organization or an advocacy group.

(More ambitiously, this segment might include a pre-recorded piece from time to time.)

Segment 6: THE PUSH/THE MIC DROP (3 minutes)
This is a straight-to-camera essay that summarizes what we know, what we think and what we want to do. Most of this is written in advance but it also includes drop-in excerpts from what we’ve heard in the show. This is our final call to action. 

HALF HOUR

WHAT WE KNOW:
Segment 1: INTRO/EXPLAINER (5 minutes)
Intro / explanation of topic: Discussion of how the topic is normally presented. This is an antidote for the “this person vs. that person” style of discussion. Maybe a couple anecdotes about why we’re discussing it how. (2 mins) 

Three-minute mix of animation, stats and facts  (3 mins)

BREAK

WHAT WE THINK
Segment 2: ROUNDTABLE (8 minutes)
Interspersed with video-submitted questions from the audience and questions via social
Need to break this up into a series of three issues about the topic, would see that on-screen similar to how ESPN shows the various topics it’s discussing 
BREAK

WHAT WE’RE DOING (3 minutes)
Segment 3: 
Conversation between the hosts and perhaps a guest about how someone can take part or solve this problem. Could be research, could be volunteering. 

Mic Drop: A one-minute straight to camera about what we’ve heard and seen
Possible show topics:
Why are so many people here killed by guns?
How can you make a living as an artist?
Is Chicago’s food scene the most innovative in the country?
Why is Chicago so corrupt?
What would it take for Chicago to become the next Silicon Valley?

Some final show notes:
Each piece of the show will exist in parts that will be broken down into social-friendly components.

It will be extremely important that this show is not shot in a typical studio environment. If this comes across like a CNN panel, we’re sunk. Think more about the average co-working space or a “teaming area” you’d see at an agency. The roundtable segments will need to feel / look as if the viewer is eavesdropping on a conversation. They shouldn’t start with a moderator controlling the conversation nor should we be aware of the camera through showy zooms, etc.

We’ll also need to see a variety of viewpoints. Again, this can’t be set up as “one side thinks this, another side thinks that.”

The 13 week editorial calendar will likely include a handful of topics that we go back to again and again in each season/cycle like gun violence, equality, civil rights, climate change, privacy. But instead of broad topics like this, we’ll delve into micro issues through personal stories. But it also lets us follow up on topics and people so viewers can follow the ongoing story. (Our social and web presence will also be key to this in our off-periods.)

Who is the audience? How do we know this will work?
As we’ve said, this is tailored to an under 40 audience. I’ve outlined above how this is tailored to their news interests. Some of these same values are shared by the Gen X audience, particularly the community aspects of it.

I look at stories like this that show how a broad issue – gentrification – is told through a personal story and see that it works.

And how there’s usually a deeper story to be told in these kinds of viral conversations.

Also, I’ve been asking people what they want more of in media. The above outline reflects a lot of that but puts it in a national context, instead of a local one.

Plus, this social-driven approach is something other news organizations are doing. For instance, Pro Publica does itTheir Get Involved page shows you how it’s done.

Final thoughts
The above should be the start of a conversation. From a production standpoint, there may be things we need to scale back on and begin as an experiment.

But there’s something here that would be unique and meeting a consumer demand.

The South Side is a myth: Tuesday Funk, July 5th, 2016

16thstreettower

With The Frunchroom taking up most of my live lit energy in the last year, I didn’t have as much time as I liked to do live readings. I’m trying to get back into the habit and reading at Tuesday Funk earlier this summer was a good way to do it.

This idea was kicking around in the back of my brain for a while. It felt appropriate for this series since it’s held in a Far North Side neighborhood that was not only adjacent to some of the issues discussed but also more likely to have an audience that was open to hearing it.

A couple notes: There are a couple of time-specific references in this piece, so know that I’m speaking of earlier this summer, not now. I changed a couple instances of “there” to “here.”

And if you like watching and listening to things rather than reading them, scroll to the bottom of this post to watch the video.

There are a handful of books I recommend to people who want to understand Chicago. And, yes, I’m starting this piece off with a reading list but, look, if you don’t like anything else I have to say at least I’ve given you some options for something better. Think of it like Amazon’s recommendation list in reverse. “People who also disliked this reader at Tuesday Funk bought the following…”

Anyway, if you want to understand Chicago politics start with American Pharoah, Adam Cohen and Elizabeth Taylor’s biography of Richard J. Daley and Fire on the Prairie, Gary Rivlin’s book about Harold Washington. If you want to know more about the sectarian, tribal mix of people who call themselves Chicagoans you can’t do much better than Studs Terkel’s Division Street: America. And if you want to understand Chicago’s influence and status as an innovator in everything from architecture to television to literature, read The Third Coast by Thomas Dyja.

Those four books are a great place to start, but they mostly tell you about the past. Natalie Y. Moore’s book The South Side, released just this year, is required reading about Chicago because it tells you about our present and updates the past that Cohen, Taylor, Rivlin, Dyja and Studs all explore.

What’s so essential about Moore’s book is how it argues against myth through a mix of facts and memoir. Against a historical context, Moore explains her own experiences with segregation, the real estate crisis, gun violence, political movements, the decline of the middle class – black and otherwise – and Chicago as the epicenter of social change, good and bad. Moore’s life experience fills in the gaps between headlines and stereotypes. Within chapters like “Notes from a Black Gentrifier,” “Kale Is The New Collard” and “We Are Not Chiraq” lives the nuance of stories often untold.

It’s the kind of nuance that’s tough to fit into a headline, especially headlines about the South Side. The more I thought about it, the more I realized the South Side defies easy explanations.

***

The other day I was talking with these two guys named Max Grinnell and Bill Savage. Max is a writer, professor and University of Chicago graduate. Bill’s a professor, too, as well as a renowned Chicago historian, writer/editor and former bartender. We were talking at that well-known gathering spot for gadflies, loudmouths and public intellectuals called Twitter.

Anyway, about a week ago, Max mentioned his former Hyde Park residency and noted, in an aside, “to some, that’s not the ‘real’ South Side.” Bill replied that “people who say Hyde Park is not the South Side promote a narrow view of the South Side they otherwise despise.”

They’re both correct though I’m not sure such a view is limited to those on any particular side of Chicago. For some who’ve never ventured south of Roosevelt, there’s a desire to convince themselves there is good reason never to have done so, to paint the South Side with the broadest brush possible or tell themselves that Hyde Park has something other South Side neighborhoods do not – like museums or a university or lakefront.

For some who live there, this reaction is something akin to an internal pathology borne of anger: surviving a lack for jobs and feeling overwhelmed by the violence that’s a part of some areas becomes a badge of honor others won’t be allowed to claim.

To make it very clear, the South Side contains multitudes.

31st Street Beach is great if you love water and clean beaches, but hate crowds.

For sheer beauty, heading south on Lake Shore Drive beats the drive north any day, especially if you end up at Promontory Point and walk around.

Maria’s in Bridgeport is one of the city’s great bars.

Vito and Nick’s in Ashburn serves one of the best thin-crust, tavern-style pizzas.

Lem’s in Chatham is barbecue, period, end of sentence.

You can tour a damn submarine at the Museum of Science and Industry.

Pullman contains the city’s only national monument and you can get one of the best burgers and ice cream cones in Chicago at Top Notch Burgers on 95th Street and Rainbow Cone on Western and 91st, which are within five minutes of each other in Beverly.

And that’s just the stuff that Channel 11 will cover. Nevermind the stuff only locals know and oh by the way there’s going to be a presidential library down here in a few years so go now and beat the crowds.

But denying the real South Side also includes Hyde Park or, say, Beverly depends on the tired idea that there are nice neighborhoods and bad neighborhoods – that the problems that plague our city stop at boundaries that are a bigger concern for real estate agents than criminals. It also means denying the nuance within neighborhoods, the prosperity that often lives close to danger.

I live in Morgan Park which is about as far on the southwest side as you can live and still be in Chicago. On the whole, it’s pretty nice with some areas you might diplomatically call “dicey.”

Last week, four people, including a pregnant woman were shot and wounded in Morgan Park.

But the day after that I walked block after block, taking pictures of the historic bungalows, Queen Anne homes and old mansions that populate the neighborhood, blocks that contain more than a few Chicago landmarks and designs by Frank Lloyd Wright. The sun was out.

Three days ago, a man was shot in Morgan Park by the father of his ex-girlfriend. This happened roughly a mile from my tree-lined street with its well-maintained lawns, some professionally so.

I’m barely a block from a park which holds an easter egg hunt every year. It was on this street – my street – two years ago that a couple of guys robbed me at gunpoint two doors down from my house. When a lawyer for one of the guys showed up in my driveway with a subpoena, the first words out of his mouth were “This is a beautiful street. I can’t believe you got robbed here!”

Yeah, me neither.

I could tell you about the pro-am cycling event Morgan Park will host in a little over a week, the annual art walk in October or the live lit series much like this one that I host once a quarter.

I could tell you about all that in an effort to convince you that even within a particular neighborhood nothing is all good or all bad or remind you of the times people have been shot in tourist districts downtown or what we’d call a riot in one neighborhood is called a post-game celebration in another but sometimes it feels like I’m belaboring the point, which is this:

Myths are stories we tell ourselves to explain things that seem far away, things we don’t understand. For a lot of people, the South Side is a myth.

Are there very real problems of poverty and violence in some parts of the South Side? Yes. Let me state unequivocally that there are people living in some places here who would leave if they could escape it. But those blocks – and they are blocks not neighborhoods – are no more or less representative of the entire South Side than Edegwater, Rogers Park, Lincoln Park, Lakeview or Wicker Park are completely representative of the North Side.

That’s what’s always struck me: how often problematic areas on the North Side are referred to by their neighborhoods, while shootings are often said to be happening on the South Side. When good things are happening on the South Side, we often speak of them as exceptions or grade them on a curve. Residents of visitors describing a restaurant or bar as “pretty good for the South Side” is literally why we can’t have nice things.

***

Natalie Moore’s book The South Side is a welcome corrective after years of reporting that has focused on the negative of that part of the city. It doesn’t offer easy explanations. Instead, it embraces the complexity of its subject and describes how policy becomes personal. At some point, if you want to get people to stop believing in myths, you have to replace them with your own stories based in science, fact and experience.

While few of us are ever going to write our own book on the complex parts of Chicago we love, we’re all capable of creating the culture we want. Even if it takes a bit of nuance.

METX 204 at 16th Street Tower image by vixla via Creative Commons license.

Rainbow Cone is Chicago’s original family dynasty

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The piece below is something I wrote for a now-abandoned project about unique Chicago places. With Rainbow Cone‘s grand opening this weekend and the store celebrating its 90th anniversary this year, I thought it was right to publish it now.

If there was any justice in the world, the family name most closely associated with the greatness of Chicago would not be The Daleys.

It would be The Sapps.

Sure, the Daleys built O’Hare, Millennium Park and several other monuments to Chicago’s spirit of ingenuity triumphing over reason. But in 1926, when Old Man Daley was still finding his way around Bridgeport, Joseph Sapp and his wife Katherine built Original Rainbow Cone, a small store at 92nd Street and South Western Avenue that sold a unique, five-flavor ice cream treat of the same name. Some 88 years later, the store is in roughly the same location as when it opened and a Rainbow Cone remains one of the finest desserts known to man, woman or child.

The Rainbow Cone is a both an engineering marvel and a kid’s fantasy come true. Literally. The story goes that the New York-born Sapp grew up as an orphan on an Ohio work farm and had few indulgences, save for the times he could save up enough money for ice cream. At the time, he had two choices: chocolate and vanilla. Rather than a single serving of one or the other, Sapp envisioned a carnival of flavors perched on his cone. As an adult, he brought this vision to life:

Orange Sherbet.
Pistachio.
Palmer House.
Strawberry.
Chocolate.

That’s what it looks like, top to bottom. Five layers of ice cream, which could fairly be called slabs. They are not scoops. In a city once known as Hog Butcher to the World, this seems right. It also seems right that Chicago’s most famous ice cream should be built one level at a time like the skyscrapers the city invented. The slender cone below never seems quite up to the task of supporting it all, but it perseveres.

The Palmer House flavor always intrigued me: Venetian vanilla with cherries and walnuts. For a long time, I assumed it was invented, like the chocolate fudge brownie, by the legendary Chicago hotel of the same name. According to Joseph’s granddaughter Lynn, who has run Rainbow Cone since the 1980s, a New York dairy had a vanilla-and-cherries flavor called Palmer. Joseph added walnuts to the ice cream and “House” in honor of the hotel; he and his wife were equally savvy about marketing and making ice cream.

Once assembled, the ice cream often forms the shape of a scalene triangle, the orange sherbet layer valiantly holding it together over the top. It is possible to order a small Rainbow Cone from the menu but even then its size recalls a slice of Chicago’s famed deep-dish pizza. Lynn says Joseph’s original recipe was designed to be chock full of as much nutrition as possible – mainly from the fruits and nuts. His motto then was “Ice cream is good food. Eat ice cream daily.”

It begins melting immediately, as fleeting as a Chicago summer. And it’s delicious. If I were a proper food critic, I might be able to describe why it works so well or contrast the way it’s made with similar frozen treats. All I can tell you is it tastes like roller coasters and a run through the sprinkler and staying at the park until 9 p.m. and all the joys afforded by the warmth of the sun.

For those with an allergy, there’s a nut-free version that I understand is just as good. You can also get rainbow ice cream cakes and sundaes with various other flavors. I know this because it’s on the menu, but I’ve never had any of it. You can also get quarts of Rainbow Cone through December. I never have. The scarcity is part of the anticipation. What’s the fun in wanting something you can have anytime?

The ice cream aside, it’s important to understand why opening Rainbow Cone was sort of a crazy thing to do though perhaps no more or less crazy than raising up the buildings of downtown Chicago some ten feet through the use of jackscrews so an underground sewage system could be built. (Look it up.)

It gets cold in Chicago. Very cold. For months. So the window of opportunity for convincing people to leave their warm houses and buy something that will make them colder is a small one. Rainbow Cone closes for the season at the beginning of November and opens again in early March, which is so much wishful thinking. This year, I went to Rainbow Cone two weeks after it opened and took a picture of the cone piled high with multi-colored ice cream, my hand wrapped triumphantly around it. “Suck it, winter,” read the caption when I posted it to social media. Nevermind you can see a good foot-and-a-half of snow on the ground in the background of the picture. I think it eventually melted in April.

Also, Rainbow Cone was built in what is now the vibrant neighborhood of Beverly on the Far South Side of Chicago. But back in 1926, that area of the city was still developing and known for the number of cemeteries there. According to Lynn, Joseph realized there was a market in the relatives of those dearly departed who would come to visit them. On their way back into the city, they’d need something to lift their spirits and they’d stop at Rainbow Cone. Even now, Sundays remain Rainbow Cone’s busiest day.

The unique two-story design of the Rainbow Cone store is mean to evoke the fluffy ice cream it serves. Pepto-Bismol pink stucco with orange Spanish-style roof tiles. The doorway trimmed in rainbow-colored bricks. A towering Rainbow Cone on the roof. Neon letters offering “Cakes For Any Occasion.” It stands just across the street from the original location, on the border of Chicago and the village of Evergreen Park. The suburb recently removed acres of trees and green space to build big box stores and a gas station. It is as if Rainbow Cone stands at the entrance of the city, a guardian meant to preserve Chicago’s past.

Rainbow Cone remains a family business. Joseph’s son Bob and his wife Jean ran it in the 1960s and 70s and their daughter Lynn took it over from them. Outlasting the imitators (it’s not called Original Rainbow Cone for nothing), it’s been served up at Taste of Chicago for the last 27 years and functioned as the city’s culinary ambassador at events in Washington, D.C. and Los Angeles.

Rainbow Cone has been a part of South Side childhoods for decades. The ice cream is certainly delicious. But I go back there several times a summer as a reminder of what you can do when you leave behind all the reasons why you shouldn’t do something and think about what you dreamed of making as a kid. Chicago has always given me a place to do that.

I’m sure the Daleys would say the same.