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Year In Review: Trump's 5 Biggest Clashes With Chicago In 2017

The president and the city were constant sparring partners throughout the year. But who won in the end?

CHICAGO, IL — Ask most Americans about the biggest fights of 2017, and they would probably point to Floyd Mayweather's beat down of Colin McGregor. Or maybe the "he said, she said" exchanges between Rob Kardashian and Blac Chyna. Some Chicagoans would even point to the scuffle between Bulls teammates Bobby Portis and Nikola Mirotic that left Mirotic with a shattered jaw earlier this season. But for sheer magnitude, duration, drama and audacity, the highest of this year's high-profile feuds was between President Donald Trump and the City of Chicago.

Throughout 2017, the back and forth between Trump and Chicago officials — particularly Mayor Rahm Emanuel and, usually by extension, Chicago police Supt. Eddie Johnson — played out like some twisted Matthew McConaughey-Kate Hudson rom-com that, by the end, had spectators yelling at the participants to quit fighting and start dating already. The only missing elements were co-starring roles for Judy Greer and Steve Zahn as the sympathetic but snarky best firends.

Actually, that wasn't the only thing missing; the feud also had very little intentional humor, making it more of a prize fight than a romantic comedy. It was the Don vs. Rahm, the Second City Skirmish, When Chicago Crime Hit Primetime. Patch takes a look at the five big rounds of thumps from Trump and bombs from Rahm and declares a winner in the War Over the Windy City.

Find out what's happening in Chicagofor free with the latest updates from Patch.

Round 1: "Send In The Feds"

If the 45-minute meeting between Trump and Emanuel in December of 2016 was like the pre-fight hype of a weigh-in, then the president's criticism in January of how officials were handling the city's rampant crime and gun violence was the equivalent of charging out of the corner swinging once the bell rang.

THE STORY: Trump's 'Send In The Feds' Threat: Chicago Officials Welcome Help But Not The National Guard

Find out what's happening in Chicagofor free with the latest updates from Patch.

And Trump connected. Hard. First came the message, "Standing Up For Our Law Enforcement Community," published on the White House website on Inauguration Day that called out Chicago for the "thousands of shootings" in the city in 2016. Days later, Trump wrote this infamous Twitter post:

"If Chicago doesn't fix the horrible 'carnage' going on, 228 shootings in 2017 with 42 killings (up 24% from 2016), I will send in the Feds!"

The ominous threat sent Emanuel's administration reeling, and it even generated responses from Chicago activists and Illinois Gov. Bruce Rauner. Trump never followed up on — or even really explained — his ultimatum, but it didn't matter. He sent Chicago to the mat.

WINNER: Trump with a knock down.

Round 2: Protesting the President

While the city's elected officials ended the first round with a standing eight count thanks to Trump's opening salvo, Chicagoans were less stunned by the president's wallop. Protesters demonstrated in front of Wabash Avenue's Trump International Hotel and Tower on Inauguration Day, an event that led to an impromptu nighttime march throughout the Loop. That protest was followed by the Women's March on Chicago, one of the largest of the series of national demonstrations that occurred the day after Trump's inauguration.


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The real haymaker, though, came with February's "Operation: Kiss Our Asses, Release Your Taxes." The demonstration had more than 1,000 people aim their bare bottoms at Trump Tower in cold temperatures to demand the president release his tax information.

WINNER: Chicago with the kind of staggering knock down that only the raw fury of naked butts can deliver.

Round 3: Trump's Crime Jabs

After the flashy displays of the early rounds, both fighters settled into steady, predictable patterns of punch-defend-counterpunch. Trump consistently worked the body of Chicago's biggest weakness, its epidemic levels of shootings and murders.

THE STORY: Trump Calls Chicago A War Zone (Again), Cites 'Alternate Facts' About U.S. Murder Rate (Again)

Although the president's jabs bruised the city's reputation at the national level, his attacks had a major flaw: They were usually based on wrong and misleading information. No holds barred might fly in a street brawl, but for a public battle in the political arena, rules apply or it's anarchy. Anarchy! Human sacrifice! Dogs and cats, living together! Mass hysteria!

WINNER: Draw. Trump wins the round but is deducted points for hitting below the belt with "fake info."

Round 4: Rahm Strikes Back

If Trump's go-to tactic was going after Chicago officials on crime, Emanuel relied on shots that struck the president's national policies, such as health care reform and a transgender military ban. His most cutting response, however, came following the president's first-ever address to a joint session of Congress in March. Emanuel publicly questioned whether Trump actually cared about ending Chicago's crime and violence problems after the president's speech cited the city's murder rate.


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The mayor's blows might've landed, but they certainly didn't stop Trump from continuing his charge.

WINNER: Draw

Round 5: Lawsuit Loss

Trump vs. the City of Chicago might have played out in soundbites and Twitter posts for most of the year, but this fight's most decisive action actually happened in the courtroom. In September, a federal judge in Chicago struck down the new requirements imposed by the U.S. Department of Justice for law enforcement grants that city attorneys contended were unlawful and sought to punish sanctuary cities.

Both sides held nothing back in this exchange over crime, as well as the status of some U.S. cities and jurisdictions as safe havens for undocumented immigrants. Chicago officials argued the administration overstepped with the new grant standards, requiring cities to agree to violate people's constitutional rights in order to qualify for federal money. Trump's attorney general, Jeff Sessions, blasted local leaders for adopting "an official policy of protecting criminal aliens who prey on their own residents" and blamed them for "the unprecedented violent crime surge in Chicago."


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But U.S. District Judge Harry Leinenweber sided with the city in a 41-page ruling that granted a preliminary injuction to block the revised guidelines for the Edward Byrne Memorial Justice Assistance Grant program. To add insult to judicial injury, Leinenweber also denied Sessions' motion to limit the ruling only to Chicago, meaning the decision was seen as a victory for sanctuary cities around the country.

WINNER: Chicago, winning the round and the bout with a technical knock out.

As 2017 comes to a close, Chicago appears to be the battered champ in its first free-for-all with Trump, especially with the news that the city will end the year with fewer murders than last year. But if there's one part of the fight game that holds true — whether in sports or in politics — it's to always expect a rematch.

RELATED: Chicago's Murder Rates Down In 2017, But Still Shockingly High

Who's ready for the War Over the Windy City II in 2018?


President Donald Trump (left) and Mayor Rahm Emanuel (Photos via Patch archive)

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