President Donald Trump might’ve met his match with Chicago Mayor Brandon Johnson. We’ve been keeping you updated with all the drama and fallout between the two leaders after the president symbolically declared war on the midwestern city. With threats of the National Guard and ICE agents being sent to Chicago, Johnson promised he’s not going down without a fight.
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In truth, the mayor is in a unique position as a Black man and Democrat continuously targeted by the Trump administration. That’s why he’s been coming for Trump and undermining his plans to turn Chicago into a battleground. From writing executive orders of his own to giving Trump some shady advice, here are all of the times Johnson proved he can get down with Trump… no matter how low he goes.
Statement on the Ruling in the Lawsuit
On Oct. 9, 2025, a judge ruled in favor of Chicago against Trump’s deployment of the National Guard. Mayor Johnson called the victory “a win for the people of Chicago and the rule of law.” He continued in a statement calling the deployment “illegal, unconstitutional, dangerous, and unnecessary.” But what’s most notable is Johnson’s assertion that the people in Chicago are not the threat that Trump previously suggested. “There is no rebellion in Chicago. There are just good people standing up for what is right,” Johnson added.
‘What Happened to America First?’
The president recently announced a $20 billion bailout to Argentina, which has expectedly drawn criticism from folks like Johnson who say it is a waste of government money. “Argentina gets $20 billion and the South Side gets nothing,” the mayor began in a statement. “What happened to America First?”
He went on to detail plans– which would bring money, jobs and security to the city– and how Trump has undermined it all. “Right when we are finally on the brink of moving forward, Trump just cut off the funding,” he continued. “From public safety to public education to public transit, this president is cutting the services that working people rely upon.” And let’s not forget Trump’s billion-dollar bailout comes as the federal shutdown enters its third week.
Trump Is ‘Beneath the Honor of Our Nation’
For weeks, Trump has been taunting Mayor Johnson and the city of Chicago with threats of sending in the Guard. Back in September, this led Johnson to respond to AI memes posted by the president. “The President’s threats are beneath the honor of our nation, but the reality is that he wants to occupy our city and break our Constitution,” he began on X. “We must defend our democracy from this authoritarianism by protecting each other and protecting Chicago from Donald Trump.”
Chicago Police Will Not ‘Collaborate’ with Guard Troops
Johnson signed an executive order declaring that the Chicago Police Department doesn’t take order from anyone other than himself. He said the department will not “collaborate with federal agents on joint law enforcement patrols, arrest operations, or other law enforcement duties including civil immigration enforcement.” Johnson said the order “gives a clear directive” about who’s really in charge, POLITICO reported. “This is about making a clear distinction about what our law enforcement engages in vs. what the federal government engages in. This president is not going to come in and deputize our police department.”
Johnson Calls Trump an ‘Unstable, Unhinged, a Double-Minded Individual’
Responding to Trump’s call to have him and Ill. Gov. JB Pritzker jailed, Johnson told CNN that the president is simply an “unstable, unhinged, a double-minded individual that quite frankly is a threat to our democracy.” He continued saying he wasn’t shocked by Trump’s threats because this isn’t the first time he’s called for “the arresting of a Black man unjustly.”
Johnson Explains Trump’s True Motives
In a recent interview with MSNBC, Mayor Johnson explained Trump’s true motives. “It’s not about immigration, and it’s certainly not about crime,” he began. “This president and this administration cannot be trusted,” the mayor continued, adding that the city of Chicago will hold Trump accountable. He encouraged all Americans to “push back against this tyrant.”
Johnson even referenced Trump allegedly trying to undo the progress made after the Civil War– when slavery officially ended in America. “This president is literally attacking the sanctity of what this democracy is about,” he said.
‘Not in Chicago’
Mayor Johnson isn’t impressed or stressed about Secretary of Homeland Security Kristi Noem recent TSA promo videos. If you haven’t noticed yet, when you walk through TSA at many airports, a video of Noem blaming Democrats for the current government shutdown plays… Well, Mayor Johnson said he’s not having any of this going down in his city. In a simple tweet, he wrote “Not in Chicago.”
Johnson Responds After Trump Calls Him ‘Incompetent’
After Trump called Johnson “incompetent,” the mayor spoke out condemning the National Guard deployment. “The problem with the President’s approach is that it is uncoordinated, uncalled for, and unsound. Unlawfully deploying the National Guard to Chicago has the potential to inflame tensions between residents and law enforcement when we know that trust between police and residents is foundational to building safer communities,” he said. “An unlawful deployment would be unsustainable and would threaten to undermine the historic progress we have made.”
The City Responds
Johnson is trying anything he can to slow down ICE and Guard troops from invading his city. On Oct. 6, he signed an executive order designating ICE-free zones around the city. The goal is to protect Chicago residents from being targeted by the Trump administration’s efforts. “City property and unwilling private businesses will not longer serve as staging grounds for these raids,” Johnson said in a press conference.
Interview With Rolling Stone
In an interview with Rolling Stone, the mayor criticized Trump’s immigration agenda. “Ripping families apart and disappearing people do not make our cities safer,” he said. “These unconstitutional actions incite fear in our immigrant communities and cause more problems than they solve,” Johnson continued.
He went on to explain that immigrants “are a critical part of the rich social fabric of our city.” The mayor added, “We will always fight for the rights and dignity of all Chicagoans [and] continue to work with community-based organizations and legal groups to ensure that all Chicagoans know their rights.”
Mayor Wants Trump to Restore the Budget
Johnson spoke to journalist Don Lemon about what he would tell President Trump to his face. “Invest in people,” he began, adding that Trump has “declared war on poverty” while doing nothing to curve the growing socioeconomic gaps in the nation.
“If you’re serious about reducing crime, then restore the $800 million for violence prevention that you took out of the budget,” Johnson continued. “If we’re gonna built safe and affordable communities, the best way to do that is by investing in people and not the ultra rich.”
Johnson’s Response to Federal Probe
We previously told you all about the Department of Justice’s investigation into Johnson’s hiring practices after accusing the mayor of discrimination. He responded to the matter calling out Trump’s cabinet– which only has one Black man in his cabinet.
“What’s clear is that not only does the Trump administration not respect the rule of law or what’s sensible about our society, you would be hard-pressed to find qualified individuals who are in his administration,” Johnson said, according to ABC News. “As my administration reflects the country— reflects the city, his [Trump’s] administration reflects the country club.”
‘They Are Lining Their Own Pockets’
Mayor Johnson called out Trump for throwing money to hire ICE agents while neglecting the needs of Chicago. “The money that the Republicans gave to ICE is more than the funding allocated to police by state and local governments in all 50 states and the District of Columbia combined,” Johnson said. “They are lining their own pockets and the pockets of the executives of a small number of corporations.”
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