Forget the media. Chicago is emerging as one of President Donald Trump’s favorite punching bags, the big city he loves to hate.

The president barely gets through a few days without sounding off on Chicago violence, often casting the nation’s third largest city as a war-torn wasteland. He whacked it yet again on Twitter Thursday evening, then followed with another haymaker Friday morning in his CPAC speech.


He’s already threatened to “send in the feds,” if Mayor Rahm Emanuel didn’t do something about the “carnage.” He’s proposed reinstating stop-and-frisk policies, compared the city to Afghanistan and even once bragged he could solve the city’s crime problem in a week.

While it’s long been a favorite target of conservatives who view it as a den of Democratic voter fraud and a Midwestern metropolis with tough gun laws that do nothing to quell violence, Trump’s frequent potshots have struck a nerve, leaving local officials to wonder what’s behind the obsession with Chicago.

“I think the president is still upset that we did not allow him to use our city as a backdrop for a campaign stop,” said Chicago Alderman Carlos Ramirez-Rosa, who has led some of the city’s opposition to the president. “We didn’t give him a forum. I think he’s still getting over that.”

Trump’s criticisms are grounded in fact — homicides and shootings have surged — but it’s also true that the City of Big Shoulders has had its own tendency to hit Trump hard, sometimes close to the belt.

Last summer, for instance, Chicago protesters thwarted Trump’s attempt to hold a large campaign rally in the city, essentially booing him off the stage before he could step foot onto it.

Activists posed as Trump supporters to enter the University of Illinois at Chicago arena for the rally. Then they disrupted the event, tearing up campaign signs and shouting anti-Trump chants. Trump never arrived, canceling amid security concerns and lamenting “thugs” in Chicago as the cause.

Donald Trump and his children Eric, Ivanka, and Donald Jr., attend a press conference at the Trump International Hotel and Tower in Chicago on Sep. 24, 2008. | Getty

Trump supporters, some of whom drove in from other states to see their candidate, went home with heads hanging, all part of an ugly scene that played on an endless loop on cable television networks.

Last fall, honorary street signs bearing Trump’s name disappeared right around the time aldermen publicly mulled removing them. That was after Chicagoans drove a trending Instagram meme of posing in front of Trump Tower — while flipping it off.

In November, the City Council codified its repugnance. It officially revoked the “Trump Plaza” designation around Chicago’s Trump International Hotel & Tower, saying in an ordinance that Trump’s “mean-spirited remarks about Chicago during the first presidential debate misrepresents the City and discredits the positive attributes of the City.”

More recently, on Valentine’s Day, a jokester taped onto a Trump hotel sign a photoshopped image of Trump and Vladimir Putin, both shirtless on horseback, with the words: “From Russia with Love.”

Chicago has thumbed its nose at Trump at almost every turn. But the animosity began even before his 2016 presidential run.

In 2014, Trump engaged in an epic feud with Emanuel as well as Chicago Tribune architecture critic Blair Kamin after the New York developer added 20-foot-high letters spelling T-R-U-M-P across his 96-story hotel tower, overlooking the Chicago River. Emanuel called it “tasteless” and tried — unsuccessfully — to take it down. The Pulitzer-prize winning Kamin called it a “wart” on the city’s skyline. That only trained Trump’s gaze on Kamin. The feud went national.

“I gotta say, Chicago, this is on you,” Daily Show’s Jon Stewart said at the time. “Did you not think that Donald Trump was going to put his name on the building you let him build? It’s what he does!”

Fast forward to present day: Chicago is among the cities nationwide to stand in defiance of the president’s threat against sanctuary cities, led by a mayor who has long been a nemesis to conservatives as the foul-mouthed former chief of staff to President Obama and a Clinton White House staffer.

Emanuel, who had met privately with the soon-to-be-president at Trump Tower during the transition, tweaked Trump on a sensitive subject right after Trump’s swearing in.

“You didn’t get elected to debate the crowd size at your inaugural. You got elected to make sure that people have a job, that the economy continues to grow, people have security as it relates to their kids’ education,” Emanuel said. “It wasn’t about your crowd size. It was about their lives and their jobs.”

There’s another theory to Trump’s obsession with Chicago: It’s what the president sees on cable news. Indeed, one of Trump’s Chicago tweets followed a segment on Fox’s O’Reilly Factor that examined Chicago’s surge in shooting deaths.

The president’s fixation is grounded in a legitimate spike in violence (though he often flubs the numbers); the city, with Emanuel as mayor, has battled surging homicide and shootings. In 2016, the city recorded 783 homicides, the highest number since 1996. That’s at the same time other major cities have seen declines in their violent crime numbers.

Trump recently qualified his remarks, saying there were “two Chicagos,” one with crime issues and another without them. It was a more nuanced approach from a developer who owns a major property in the city.

Local pols point to many other fixes — aside from sending in the National Guard — that Trump could institute to lift up the communities where violence rages.

Cook County Commissioner Bridget Gainer cited statistics showing a 55 percent unemployment rate among African American males 16-24 in the South and West sides — raging hot spots for gang violence. Gainer said Trump can employ the power of the federal government with executive orders to impact Chicago’s economy on top of local efforts already underway.

“A whole country mobilized when unemployment was 25 percent. The whole economy got shifted around,” she said, referring to the Great Depression. “Will (Trump) sign an executive order for an infrastructure investment? A WPA 2.0 to employ people? That can be done in a stroke of the pen also. If you want to talk about what the vast majority of this is rooted in — there’s not enough jobs. Don’t start with law enforcement. Get the unemployment down.”