Chicago Knows Donald Trump. He's Like a Crooked Alderman on Steroids.

Trump has a sordid history with the Windy City. Pardoning criminals is just a part of it.

Donald Trump wants to send troops to Chicago. He says he’s being begged by “beautiful black women” to militarize our streets and make us safe from violent crime. It is a lie that no reporter, not in Chicago, not in Washington, and not on the Sunday news shows, should repeat.

Violent crime is down in Chicago, as it is other big cities. Violence reduction strategies funded during the Biden years are working. If Trump cared about continued progress, he would support this work. Instead, he defunded it.

In fact, Trump has never cared about violent crime in Chicago. Earlier this year, for example, Mr. Trump commuted the federal sentence of Chicago’s most violent and dangerous gang leader, Larry Hoover. Fortunately for those of us who live here, Hoover is also serving a state sentence that Trump has no power to lift. Commuting Hoover’s sentence and concern for violent crime in our streets are absolutely incompatible.

Donald Trump also pardoned more than 50 Illinois residents who were convicted or charged with participating in his January 6^th insurrection. Among them are dangerous criminals, people with prior convictions for assault and battery, for burglary, for drug possession and distribution, and for firearms violations. Commuting those sentences and concern for violent crime in our streets are, again, absolutely incompatible.

There’s another story to tell about Mr. Trump’s relationship to Chicago. It is a sordid and familiar one. The kind of story that makes you think of crooked aldermen and political hacks. It’s one where Trump’s only concern about crime is whether he benefits from it.

Chicago is a beautiful city and its motto urbs in horto means city in a garden. But some veteran City Hall watchers have quipped that a better motto would be ubi est mea — where’s mine? That’s the side of Chicago where Donald Trump is most at home.

Take his namesake tower. It is a beautiful building. It sits on the former site of the Chicago Sun Times, a site he bought in a 2001 deal with the paper’s then owner, Conrad Black. Mr. Black and his investors sold out Chicago journalism when they pocketed the profits rather than investing in the business. Later, Mr. Black was convicted of mail fraud and obstruction of justice for illegally diverting millions of dollars from his company through fraudulent non-compete payments. He received a full pardon from Mr. Trump in 2019.

Full disclosure: Before the Trump Tower was fully built, I ran for governor of Illinois against a crook in my own party. A supporter threw a fundraiser for me in the building’s model unit. I’ve never met Mr. Trump, but if you look at his campaign contributions, there’s an in-kind donation to my run against Rod Blagojevich.

That’s funny, because I’m not his kind of guy, and Mr. Blagojevich really is. In fact, Trump commuted the sentence of our ex-governor who was serving time because he got caught on tape attempting to sell the U.S. Senate seat that became vacant when Barack Obama left to become president. After his release, Rod campaigned for Mr. Trump’s reelection and when Trump returned to the White House, he pardoned Blagojevich.

Just this week, Blagojevich authored a piece for the right-wing Illinois Review arguing that Chicago is at a tipping point and in need of Trump’s military intervention. This, I scratch your back, you scratch mine relationship is not about fighting crime, it’s about looking the other way to pocket an advantage.

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The dirt isn’t just political; it’s actual pollution. When he built his Chicago tower, Mr. Trump opted for a unique cooling system that drew 20 million gallons of water each day from the Chicago River, with the then-heated water was pumped back into the river. Never mind that the system didn’t comply with environmental laws, or that it lacked permits, or that it killed thousands of fish. In 2025, Trump Tower agreed to a $4.8 million settlement under the Clean Water Act and agreed to take several steps to mitigate the environmental damage.

Then there was the story that even a Hollywood writer couldn’t make up. It takes us back to 2021, during the height of the COVID pandemic. It was the time of social distancing. Many elderly people wouldn’t leave their homes. COVID vaccines had just been approved, but the supply was limited. Across the country, vaccines were being offered only to populations most at risk. In Chicago, that meant vaccines were available only to people over 65, who are at most risk of severe illness and death from the disease and to frontline workers regularly exposed to the virus.

Loretto Hospital, a small safety-net hospital on the city’s low-income west side received an allocation of COVID vaccines to administer to the target population. What did they do? They set up a vaccination site far from the west side. In fact, at Trump Tower. Turns out, Dr. Anosh Ahmed, the hospital’s CFO, lived in the building.

The hospital was then suspended from the vaccination program. Later, Dr. Ahmed was indicted for money laundering and a multi-million-dollar COVID testing scam. According to the Block Club Chicago, he subsequently fled to Dubai. No one is alleging that the staff at Trump tower had anything to do with the very unusual vaccination effort that took place in their building. On the other hand, though he later denied it, Dr. Ahmed bragged about vaccinating Eric Trump at Trump Tower in a text message that included a photo of the two men taken on the day in question.

If all this feels more like the work of a crooked alderman than President who cares about public safety, well, it should. After all, there are the local property taxes.

Chicago is in Cook County, and every year, the county collects its property taxes from homeowners and from commercial properties like Trump Tower. The more money the commercial properties pay, the smaller the portion of the levy is left for homeowners to cover.

For many years, the assessment of real-estate was a wholly owned business subsidiary of corrupt local Democratic Party leaders. It was the party’s political cash station. The Assessor determines what commercial properties are worth. Party leaders who are also lawyers appeal those assessments on behalf of the property owners, and everybody but the homeowners win. One of the biggest players in this business, former Alderman Ed Burke, reportedly won more than $12 million in tax reductions for Trump Tower. I served on the City Council with Ed. I like him. So far as I know, unlike Mr. Blagojevich, Ed Burke did not seek a pardon or commutation from Mr. Trump when he was jailed for shaking down a businessman.

Not all of Mr. Trump’s Chicago connections are related to his namesake tower. It turns out that a small Chicago bank, The Federal Savings Bank, was once owned by a man named Stephen Calk. When Rahm Emanuel was mayor, Calk’s bank received $3.6 million in city job training money. Later Calk’s bank made $16 million in loans to Paul Manafort, Trump’s Russia-connected campaign manager. Calk then served on the Trump campaign’s economic advisory committee and tried to buy his way into Trump’s cabinet. It didn’t work out. Calk was convicted of trying to bribe Manafort and went to jail for one year. Manafort was convicted of financial crimes relating to his work for pro-Russian Ukrainian political leaders. Trump pardoned Manafort but not Calk.

None of these stories hints that Mr. Trump cares about crime, unless he can somehow be the beneficiary. So, when reporters talk about sending troops into the city, they might say it is an autocratic show of force. They might say it is an attempt to suppress Democratic votes. They might say it is about intimidating political opponents. They might even look to see if the troops are housed at taxpayer expense in Trump Tower. But they must not say it has anything to do with crime on our streets.

Edwin Eisendrath hosts “It’s the Democracy, Stupid” on Lincoln Square and "The Big Picture" on WCPT820 AM/ Heartland Signal. You can follow him on BlueSky at eisendrath.net and Substack at “It’s the Democracy, Stupid.” Read the original column here.

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