Chicago’s downtown mirage and how ‘Boss Daley’ was Trump before Trump

Jeremy Borden
The Untold Story
Published in
7 min readJan 25, 2019
Photo by Chris Palomar on Unsplash.

Take a look at that skyline. The descent into O’Hare, skirting the Lake Michigan shore, being enveloped by that steel and glass panoply ripped from Architecture’s Digest is a well-orchestrated delight. It’s enough to inspire even the most cynical to wonder, ‘Who built that?’

The Chicago skyline — and I would bet it could be argued those of other large metropolises, along with gilded statehouses and City Halls across the country — belies its darker history.

In “Boss,” the 1971 biography about the late downtown champion Mayor Richard J. Daley, Mike Royko brutally dismantles the six-term mayor who controlled Chicago for 21 years through his masterful command of the Democratic Party Machine. For the Machine loyalists, Daley inspired awe because he was a master puppeteer: deflecting any legitimate challenge from any progressive Republican*, squelching intra-party feuds and allowing the corruption that greased the Machine’s squeaky wheel to plod along unless it directly challenged his power.

If I want to be charitable, Daley was a man of his time who couldn’t have done more than he did inside the already-corrupt system he had grown up in and mastered by the time he ran for mayor. Catering to downtown business interests was the smart political route and look at the results: a downtown teeming with jobs and clean streets that has built up legends of banking, retail and advertising while providing a palate for some of the best modern downtown architecture in the world.

But that’s not really a charitable view, it’s more like the convenient glossing over of a stark but dedicated two-faced political life that systematically and intentionally destroyed black and brown communities by displacing families and exacerbating and deepening poverty on the city’s South and West sides. Many in those communities — after years of progressive rhetoric and false promises from the solidly blue city’s leaders— are now fleeing Chicago, some 40,000 African Americans between 2015 and 2016 alone, the affects of a long-broken political system cemented in the Daley years. The City of Broad Shoulders chasing away its working class as a gilded downtown playground continues its ascent is an irony that should be impossible to square.

Just like Trump, Daley was a master at making the party Machine do his bidding while voters were herded like sheep. Daley, though, was arguably even more overt in his corruption. Plied by city jobs or more coercive means, vote machine rigging and bribes, The Mayor always got the right turnout, election after election. The Democratic Machine in Chicago pushed policies and handed out city jobs that helped well-connected whites, particularly those from Daley’s Irish enclave of Bridgeport.

Daley’s promise to build a city that meant opportunity for everyone was lost somewhere along the way.

Yes, this is all somewhat familiar. Just as Trump’s friends and businesses are doing quite well as foreign governments and corporations help pad his bottom line, Trump’s central campaign promise to return jobs he claims were stolen by immigrants will be equally disappointing. And while I get that the wall is as much or more about race and the threat of the “other,” the economic promise cinched a base eager for what they remember as a simpler time when economic prosperity was at hand. (No matter that prosperity was usually the province solely of white men.) He wants to build a wall to keep them out — when really it’s automation where, for example, a few machines can produce more steel than dozens of workers with healthcare problems to pay for.

The Trump-Daley hypocritical alliance is also something to marvel at.

Check out this doozy … Royko writes:

Daley was a pious man — faithful to his church a believer in the Fourth of July, apple pie, motherhood, baseball, the Boy Scouts, the flag, sitting down to dinner with the family and deeply offended by public displays of immorality.

And then in a seemingly unrelated passage about Chicago :

The question has never been how you made it, but if you made it. This town was built by great men who demanded that drunkards and harlots be arrested while charging them rent until the cops arrived.

Trump’s father, Fred, built housing all over greater New York City. Trump and his siblings started a shell company to pilfer their father’s profits and avoid taxes without the toil of moving one grain of sand.

The book leads up to the infamous 1968 Democratic Convention, which is a great encapsulation of Daley’s leadership. History might delude you to believe that sometimes things get out of control, that rabid protesters invaded Chicago and the police were forced to respond to the mobs.

Certainly police don’t beat people without being provoked?

Instead, Royko lays out the context — a police force that was embattled, pissed about other events that had happened in the city previously and given free rein to crack skulls.

We should be horrified when Trump winks at violence when it comes to the press, but Daley did a hell of a lot more than wink. A scene from the beginning of what became the 1968 riots near the Democratic convention:

[T]he city forced the confrontation and the police became the aggressors, striking out at militant and middle-roaders alike, involving thousands of people in the violence, and making the dominant event of the convention a battle over a few acres of grassland … The first chilling scene of a reporter being forced to surrender his notebook, a photographer his film, unfolded. A Newsweek reporter, press credentials pinned to his coat and not interfering with police, was cooly and systematically beaten. A Philadelphia newsman was told ‘Hey, you dirty bastard, give me that goddamn notebook.’ … It was clear the police were looking for reporters, that they were prime targets.

Of course, not everyone at the convention — which in those days decided who the nominee for president would be — could let Daley’s open thuggery slide. In a now-infamous exchange, Sen. Abraham Ribicoff from the convention podium compared the Daley police force’s tactics to the “gestapo.”

Ribicoff opened a floodgate of criticism that nearly tore the convention apart. The next day, Daley did what has now become a hallmark of storied American politicians: he came up with a doozy of a lie to explain the whole thing away.

According to Royko, Daley stunned the world when he told Walter Cronkite:

Let me say something I never said to anyone. It’s unfortunate … but the television industry didn’t have the information I had. There were reports and intelligence on my desk that that certain people planned to assassinate three contenders for the presidency, that certain people planned to assassinate many of the leaders, including myself. So I took the necessary precautions.

Federal officials later said Daley’s suggestion of a ‘plot’ was fiction, not that it should have explained away the mass beatings of people at the hands of Chicago police.

This is not to equivocate historical wrongs of that time with present wrongs. It is to say that those who let Daley get away with pronouncements like, “I’ve always been a liberal myself,” deserve their share of the blame in that day’s persistent cover-up.

And it took a village to cover up for the reality of Daley’s autocratic machine. As Royko tells it, the media, City Council, the Kennedys and other elite power brokers all aided and abetted.

Obviously, I don’t have all the answers, but what’s the lesson here? For me, it’s hold power to account all the time and never relent, even when it feels like your team is on the field. It isn’t all that profound to point out that Daley and Trump represent two sides of the same hypocritical coin, that, by varying degrees depending on the era, defines the American political experience. Their similarities aren’t an anomaly of history. They’re a guiding premise.

The merry go round keeps going and we’re the ones spinning it; only we can stop it and that starts by a true search for truth, not worrying about whether you’re wearing a red or blue hat, and doing the hard work of figuring out whether the status quo is actually working or whether your camp on Facebook or FOX or MSNBC has just convinced you it is. Those in power won’t do the soul-searching — they’ve already won, gotten what they want, which is a seat the gilded table.

I wonder if, in 50 years, some American kids on the way back from vacation in Mexico will be sweeping low over El Paso and see a wall. They’ll only vaguely know the story. But it could go something like this: the president had to fight those who didn’t understand what invasion would do as Americans struggled to get their factory jobs back. He battled everyone, including the media who worked for his enemies, to make it happen. That wall saved them.

Like a gleaming downtown mirage, the details won’t matter much.

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*This is not a typo. Republicans, of course, were often the progressive party in Chicago and elsewhere until after the passage of the Civil Rights Act in 1964, when the defection of South Carolina Democrat Strom Thurmond to the GOP sped up the process of the two party’s role reversal on civil rights at the federal level. The Democrats of Daley’s youth were of the same ilk that Thurmond’s when it came to civil rights, as South Carolina and the rest of the South were solidly blue up until that point. It’s worth thinking about that while Daley parroted the new liberal leanings of the Democratic Party, the one he grew up aligns more closely with the pre-1964 Democrats and the modern GOP.

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Jeremy Borden
The Untold Story

Writer, researcher, comms and political consultant in search of the untold story. Tar Heel. Lover of words, jazz, big cities, real people, Chicago sports.