Hugh Hefner: Janus in voluptatem


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


You saw this thing, right?


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.


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?


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.


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?


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

When does Govenor Rauner start punching up instead of punching down?

There’hadow a precept in good satire that you punch up, you don’t punch down.

There isn’t a similar theory about those who hold political office though you generally want to be seen as representing the average person rather than someone swelled with power and money.

Last night, I was listening to Sam Sanders’ podcast “It’s Been A Minute.” He was interviewing members of The Onion’s editorial staff about their work and someone echoed that line about punching up, not punching down. Sanders didn’t ask about it, but the line reminded me of a time when the Onion violated this rule and paid for it with a rare apology.

During the 2013 Oscars awards ceremony, the Onion attempted a joke, via Twitter, that covered the backbiting nature of Hollywood gossip, the misogynistic way female celebrities are discussed and even the way in which we sexualize young actresses. It’s a lot to squeeze into 140 characters and the Onion didn’t even come close to hitting the mark, using a nuclear-option swear word as a shortcut which got them lost in the wilderness. The underlying truth or attempted meaning was obscured by a joke that centered a young, black child within it, making her seem like the joke’s target.

We’re seeing a similar situation unfold in Illinois political circles due to the fallout over a political cartoon from the Illinois Policy Institute, a right-wing think tank with a CEO who’s often called “the de factor governor” and whose ex-staffers – up until a mass firing last night – served Illinois Governor Bruce Rauner in various roles, from chief of staff to communications and messaging.

The cartoon depicts Chicago Public Schools a young black child sitting on the sidewalk with a sign that says “NEED MONEY 4 SCHOOL” while a cigar-chomping white guy in a suit says “Sorry, kid, I’m broke” as dollar bills marked “TIF money” spill from his pockets.

IPI’s explanations about the cartoon have been similar to the justifications people made about the Onion’s cartoon: the point of the commentary was not to portray CPS students as panhandlers but to hold the white, fat-cat politicians up for ridicule and point out their hypocrisy in refusing to give money to Chicago Public Schools despite vast resources of TIF money – property tax dollars that go into a special discretionary fund controlled by politicians instead of to schools – at their disposal.

These are all worthy arguments for political commentary and ones a responsible group of adults ought to be having right now. Equally true is the idea that anyone using a young black child in caricatured form to make a point – a practice so legendarily problematic that there’s a go-to term for it – will find his or her arguments buried underneath an entirely different meaning. It makes you look like you’re punching down instead of punching up.

Incidentally, this is why having diverse staffs of writers, policy makers and communications professionals isn’t about political correctness, it’s about good business. If you don’t, this is what happens.

All of this would probably not get the kind of play it has if it didn’t align with the coded way Rauner himself has talked about Chicago Public Schools and the students it serves.

He’s described Chicago’s public schools as “prisons.” He’s said half of CPS teachers are “virtually illiterate.” He calls attempts to provide equitable funding for Chicago “a bailout.”

With IPI’s (ex-?)staff acting as an arm of Rauner’s government – officially and unofficially – the cartoon seems less like subtext and more like text.

This controversy has been going for more than a week – and jumped from being a local story to a national one – due to the governor’s bungled attempts at response after response keeping it alive (hence last night’s firings).

Refusing to call out the cartoon’s racist overtones – whatever the meaning behind it – makes Rauner look like he either agrees with the portrayal, is covering for his friends at IPI or doesn’t understand how the cartoon plays into the overall tone of his previous comments.

There’s a way to talk about the problems of our state’s education funding and even our state’s public schools without making students, teachers and the work of the people in those schools your targets.

The less focused your punch, the more likely it is you’ll hit the wrong person.

Maybe the governor should hire his next communication staffers from The Onion. They seem to have learned a lesson he hasn’t yet.

Image: U.S. Air Force photo by Jodi Martinez/Released

Will Rahm Emanuel’s future depend on Lori Lightfoot’s future as police board president?


Good morning. It’s Tuesday and Chicago doesn’t have a police board president.

This is important because we had a police board president yesterday.

As president of the police board, Lori Lightfoot has been the leading voice for police reform in Chicago since she was appointed by Mayor Emanuel in June 2015.

That is until this morning when her appointment expired with no indication from the mayor as to whether or not he would re-appoint her.

It’s a bit like the story Wesley tells in The Princess Bride of working for the Dread Pirate Roberts. Wesley served under the legendarily cutthroat Roberts but was told each night that the pirate would likely kill him in the morning.

The sun rose this morning and whether Lightfoot lives to see another day as police board president remains to be seen.

If you or I get fired or laid off, it’s for two reasons:

1. The company we work for doesn’t have enough business to support the job they hired us for
2. The people above or below us think we’re doing a bad job

Now, you’re not Lori Lightfoot with a background in criminal justice, but you read the news so you know Chicago’s police force has plenty of work to do when it comes to systemic reform, which has benefits for cops and citizens alike.

Absent a consent decree from the Justice Department, which we don’t have now and likely won’t under the Trump administration, Mayor Emanuel controls the pace of police reform. And he’s apparently put together a plan. You and I haven’t seen it. None of the groups in Chicago who work on police reform have seen it. I’m sure some of the mayor’s allies and staff have seen it.

Lori Lightfoot’s seen it though. She’s said it’s insufficient or, to use her words, “set up for failure.”

In any other job, openly and publicly criticizing your boss is a bad move. But, similar to Inspector General Joe Ferguson – another Emanuel appointee whose work involves pointing fingers at the mayor on behalf of the city’s residents – that’s Lightfoot’s job: Set a course for the city to pursue police reform and speak up when the city – and the mayor – doesn’t meet the standard.

Criticism from Lightfoot is a clear sign she’s doing a good job whether you’re the target of that criticism – the mayor – or the beneficiary of it – that’s us.

Similar to what happened before Ferguson’s re-appointment in 2013, Emanuel appears to be wavering on whether to keep Lightfoot in the role of police board president. Ferguson’s re-appointment came after a major scandal involving another mayoral appointee seemingly forced the mayor’s hand. One would think he wouldn’t want to make the the mistake twice.

We know there are plenty of good reasons why you and me and the rest of the city benefit from Wesley…er, Lori Lightfoot remaining as police board president under Rober…er, Rahm.

There’s also a political reason why the mayor should want her to remain as well. And sometimes that matters more than the good reasons.

Smarter minds than mine know that unless Rahm can demonstrate he’s serious about police reform then he’ll have a real problem getting re-elected in 2019. It won’t be impossible, but it will mean challengers with money and organization will see an opportunity.

But there’s an even more important political reason why Rahm needs Lightfoot: Trump.

Trump takes every opportunity to keep Chicago’s name in the news as a haven for violence. Last week, he even paired it with a call for state-sponsored police violence against the people police interact with in the city.

Police organizations repudiated these remarks. And Rahm will want to distance himself from them, too, though he hasn’t yet.

Let’s also not forget about that mythical motorcycle-riding cop Trump met during a visit here who supposedly has the magical formula for solving our violence problem – even though it’s likely he’s not actually a cop.

Reading Trump’s comments, you get the sense that the solution from this motorcycle-riding unicorn involves rounding up the 39,000 people on the department’s violence watch list and illegally detaining them until who knows when.

At the very least, Trump wants to put Chicago on the wrong side of the law. Not to mention on the wrong side of justice. All of which makes cops jobs harder, not easier, and puts reform further out of reach.

If Rahm wants someone good at the job of police reform, Lightfoot’s already there. If he wants to look like he’s pushing back on Trump (and his previous efforts make it seem like he does) then Lightfoot’s already there. And if he wants to win re-election in 2019, re-hiring one of his most powerful critics is a step in that direction. If for no other reason but preventing her from becoming a martyr who’s positioned to run against him.

Every morning that passes makes Rahm seem a little more like Dread Pirate Roberts. Re-appointing Lightfoot would mean they both may live to serve a little longer in their respective roles.

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.

Home for Christmas

(Note: I wrote the following back in 2009 about a now-somewhat-legendary mix of Christmas music I made in 2001. The reasons why I made it – and how, in the years since, I lost and found the joy that went into it – are what follows. I’m re-publishing it here now because I’ve finally re-created this mix on Spotify. Embed below.)


My feelings on “the holidays” have always been mixed.

Even when I was a kid, I always associated this time of year with a lot of running around. Between Christmas Eve and Christmas Day, we’d be zipping from one set of grandparents to midnight mass to our house to another set of grandparents and then back home. Then, when I was in high school, my parents divorced, which meant one more place to go on Christmas. I’d head to my Dad’s on the evening of the 23rd, then to grandma’s, then mass, then mom’s, then grandma’s, then home. A two-day, four-house gauntlet.

Then in college…well, you’re never really “home” in college, are you? The house you grew up in and the dorm with your hot plate both get tagged with that description, meaning you’re never really there. This feeling was always exacerbated by the break between Thanksgiving and New Year’s. There was a little bit of me in Chicago, and a little bit of me in Ohio.

After college, I moved into a series of apartments and this feeling of “the holiday gauntlet” was inescapable. I didn’t own a car, so I’d take the train down to the ‘burbs or have my parents pick me up, loaded down with presents and a suitcase. It never felt relaxing to me, pausing just long enough in places to eat, drink and do my best to be merry. I never really felt at home.

Look, I’m not saying being around my family is a miserable experience. It isn’t. I love them, and it doesn’t feel like Christmas to me if you’re not around friends and family. But for the ten years after my parent’s divorce, I never felt like I was in a place, emotionally or physically, to be able to fully enjoy Christmas. Again, there were good times. But I never felt like I could sit back and soak in the spirit (much less The Holy Spirit).

One of the other things I always disliked about Christmas was the music. If you want to put me through hell, make me listen to music I hate. And since most Christmas albums are cash-ins – recorded for easy money or to fulfill a contract requirement – the resulting music is generally awful. It’s not that I hated the sentiments, I just hated the arrangements.

I trace the genesis of my dislike of Christmas music back to my high school days in show choir. From 1990 to 1993, I, along with several of my classmates, spent cold December afternoons and evenings traipsing around the south suburbs singing the most common of Christmas songs. Over and over and over. (And yes, Virginia, there was accompanying choreography.) While this time period accounts for some of my most cherished memories, there is nothing more depressing than realizing you need to take “I’ll Be Home For Christmas” out of that afternoon’s repertoire because you’ll be singing at a nursing home. And I won’t even get into the lack of irony it takes for a bunch of white kids from a Catholic high school to run around singing a calypso version of “Mary’s Boy Child.” After that, I wanted to be as far away from the Christmas standards as possible.

I don’t need to rehash what most of us were feeling in the fall/winter of 2001. But I’ll tell you that my friends and family instinctually drew closer. It was against this backdrop that I decided to counteract my usual grumpiness around Christmas.

So in the winter of 2001, I set out to make a mix of Christmas songs that would give me the spirit again: The ones that married seasonal good cheer with the sense of fun that most people seemed to have this time of year. The result was A Rock and Soul Christmas. This was the cover:

Here were the liner notes:
If you know me (and undoubtedly you do as I’m not generally prone to giving presents to strangers), you know that music plays a rather important role in my life. Sadly, there are quite a few bad Christmas albums out there. Mannheim Steamroller alone has released seven of them.

So this year I set out to pull together some of my favorite Christmas songs — songs that not only expressed the spirit of the season but also didn’t, as a wise man once said, suck. While a few great tracks didn’t make the final cut (Elvis’s “Blue Christmas,” Cheech and Chong’s “Santa Claus and His Old Lady”), I think the ones that did fit the bill very well.

A note to my friends of non-Christian faiths: Though the selections here focus mainly on Christian holidays, I think the sentiments expressed within them contain universal truths that we can all appreciate during this time of year. Regardless of your expression of faith, a song like Clarence Carter’s “Back Door Santa” speaks to all of us. A note to my atheist friends: You’re all going to hell. Repent now. Just kidding.

The artwork on the cover was blatantly ripped off from A Charlie Brown Christmas as well as James Brown’s Funky Christmas. I’ll leave it to you to figure out what came from where.

I hope this CD finds you well and happy and gets you in a Christmas mood. If I can save just one person from buying A Rosie O’Donnell Christmas then it will be worth it.

Happy holidays and much love,

I sent the mix to a bunch of friends as a substitute for cards and presents and it went over really well. Every year since, I hear from one or two friends who tell me they’ve pulled out RSC during a party or while they’re opening presents. This brings me no small amount of joy.

Like most endeavors of this type, it ended up making itself. This isn’t the coolest, hippest mix of Christmas tracks ever assembled or even a collection of my personal favorites. In fact, it’s deliberately corny in some instances. Basically, I wanted to create both a Christmas-party record and a Christmas party-record. It’s also designed for all-ages listening (There’s one track on there that’s a little heavy on innuendo for the littlest ones, I suppose, but since I have friends with kids who say they play it, I’m not losing sleep over it).

I put together another mix the next year called Songs For Swinging Santas, which mixed jazz, blues, and cocktail hour together. It too was well-received, and I figured I’d do a variation on the theme each year.

Then, in 2003, I got married for the first time, which added yet another level of familial stress, not to mention more places to be, including an occasional trip to Phoenix to see my ex’s family. They were all very nice people but…well, suffice it to say there’s a fair amount of romance in the notion of a White Christmas and that gets all shot to hell in Phoenix. Plus, it was our first year as a married couple and we spent the holidays on a honeymoon cruise around the Caribbean and this, coupled with a lack of ideas as to what to do for that year’s holiday mix meant I passed on putting one together.

For a number of reasons, I lost the spirit again over the couple of years that followed. The nadir of my holiday experiences was Christmas 2005 when my marriage was breaking up. As luck would have it, we were spending the holidays in Phoenix that year. It’s not possible for me to describe how isolated and out-of-time I felt then. It was awful. One of the lowest points of my life.

The echo of that time carried through the successive holiday seasons, which brought some discord to my then-newish relationship with Erin. She loves everything about Christmas, always has. For someone whose feelings about the holidays were mixed to begin with and were now marred by an altogether unpleasant association, this was hard to take. Also – and this really is deserving of special mention – she loves The Carpenters’ Christmas Portrait. It is a holy relic to her. All due respect to Karen and Richard, but…it just wasn’t my thing.

I don’t know what lousy metaphor best describes the last couple years – a wound that’s slowly healed? A rough edge sanded over time? – but I’d found myself slowly coming around on the holidays again. This year, I noticed something weird: I was getting excited for Christmas. When I saw some Christmas trees on display, I involuntarily said “Oooh!” Out loud. I oohed, people! At first, I thought my renewed sense of Christmas spirit derived from all the folks telling me how much Rock and Soul Christmas was again adding to their Christmas celebrations. But earlier this week, I figured out what was really driving it:

For the first time in 18 years, I was going to be home for Christmas.

Or perhaps, more specifically, Erin and I would own a home for Christmas. We closed on this place during Thanksgiving week, just in time for the grind. And though we’d be running the gauntlet again this year, I was looking forward to it. Because no matter what, at the end of the day, we’d be at home together, not just in a place we called home. Not some apartment we were renting because we weren’t sure where we wanted to end up, not spending the night at our parents’ place, not in a convent singing for a bunch of nuns and mothers…no, we’d be home.

Hey, I realize that sounds trite. For God’s sakes, it’s cribbing the name of one of those cursed songs from the days of show choir. But it just makes sense now.

I’ve been blessed with many, many gifts this year. If you’re reading this post, you’re one of the people responsible since I pretty much I owe my career to the Internet. (2016 Note: This is still true, but keep in mind this was written in 2009. I think maybe 20 people read this blog then.) Eight years after I put together A Rock and Soul Christmas, I feel like I’m once again in a place where I can really enjoy it. So I’d like to share it with you.

Merry Christmas.

(Hey 2016 Me here. A couple notes on the above which is limited by what’s available on Spotify.

  • The original mix contained a different version of the Bowie/Crosby duet. It was intended as an interlude because it contained the awkward dialogue between the two at the beginning. That version feels way more Christmas-y to me.
  • The second-to-last track was originally a duet with Tom Jones and Cerys Matthews of “Baby, It’s Cold Outside.” I know how this song has been recast recently, but it’s never felt that way to me. And feminist responses to it here, here and here say it better than I could. But that’s not why it’s not here. It’s simply unavailable on Spotify (oddly, it’s the sole track off that Tom Jones album of duets that isn’t available there). That’s a shame because that version dials up the ridiculous-ness of that song and brings out the notion that the two people singing it are engaged in a consensual tete-a-tete. You can judge for yourself in the live version here: