‘What the hell is happening in Chicago’: Trump’s love/hate relationship with our city

WGN Investigates

CHICAGO — For four years, Chicago has been President Trump’s punching bag.

“What the hell is going on in Chicago?” he would frequently – and rhetorically – ask from the presidential podium.

President Trump’s taunts usually occurred after especially bloody weekends in which Chicago endured a rash of shootings, mayhem and murders. “It’s worse than some of the places in the Middle East where you have wars going on,” the president declared in the Roosevelt Room of the White House in February 2017.

It was during that meeting that a pastor said he had heard from several Chicago street gang leaders who wanted to convene a summit and lower the body count.

Pastor Darrell Scott told the president “they respect you and believe in what you’re doing.”

There was only one problem: The pastor is from Cleveland and not Chicago. The summit never happened. The carnage continued.

After an aborted campaign rally at the UIC Pavilion in 2016, candidate Donald Trump began telling a story about meeting a mythical motorcycle cop from Chicago who claimed to have the cure for crime. “I said how long will it take you to straighten out this problem” Mr. Trump later stated. “He said, ‘if you give me the authority, a couple of days.”

The president said he believed the cop really could put a cork in murders and shootings. If the motorcycle cop had the solution to Chicago’s crime plague, the president never revealed it nor publicly identified the officer.

It was until the summer of 2020 – nearly three-and-a-half-years into his term – President Trump sent in the cavalry. It came with the name “Operation Legend” and a partnership that flooded Chicago and other cities with extra FBI, ATF, DEA agents and U.S. Marshals. Mayor Lightfoot originally rejected the help, fearing it would come in the form of militarized agents, similar to what transpired in Portland. “If they try it, I’m going to use every tool at my disposal to stop them,” Lightfoot said in July. She later relented after receiving assurances that the Justice Department wasn’t planning a militarized style occupation of high crime areas. Federal prosecutors in Chicago charged 176 people as part of Operation Legend. However, Chicago still ended the year with murders up by 50%.

Trump’s team blasted progressive prosecutors who advocated for cash-free bonds.

“These guys with numerous prior felonies – 7 or 8 prior felonies with violence and guns – were let out on the street and committed another homicide. That’s not the exception. That’s increasingly the rule around here,” Attorney General William Barr told WGN News in July . “These people have criminal records and they need to be taken off the streets.”

As president, Donald Trump portrayed large cities run by Democratic politicians as chaotic capitals of anarchy run by socialists and over-run by illegal, criminally-inclined, immigrants. But it wasn’t always like this.

In 1993, developer Donald Trump flew to Gary, Indiana to lobby for a casino license. “We’re negotiating for the finest boat anywhere,” Trump said at the time. “If we’re chosen, I think Gary is going to be a very happy place. We’ll do a great job.” A decade later, Trump’s casino company declared bankruptcy and his last name was scrubbed from the betting barge in Lake Michigan.

In the early 2000’s, Donald Trump bet big on Chicago planting his namesake tower on land once occupied by the Chicago Sun-Times newsroom along the Chicago River. He boasted about the beauty of the city (and his under-construction hotel and condominium complex.

“To show you how important this project is to me, I put my children in charge and that’s very important” Trump said in 2006.

The Trump International Hotel & Tower turned into a beautiful building that more than holds its own in a city known for eye-catching architecture. Donald Trump also proved astute at understanding “The Chicago Way.” He hired now-indicted Ald. Ed Burke and his firm who successfully fought property tax assessments that wound-up saving Trump millions.

When the economy roared, Chicago’s Trump Tower still struggled. Retail space along the Chicago River was never occupied. Realtors reported the sale price of condos coincided with the president’s approval rating.

The 22-foot tall stainless steel letters that spell out the Trump name on the exterior continue to earn criticism. Ald. Gilbert Villegas recently proposed an ordinance that would revoke the sign permit for anyone convicted of treason or anyone who is convicted by the U.S. Senate after impeachment, a clear shot at Trump. 

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