At the height of Trump’s tariff negotiations, Wall Street traders developed a new strategy to make money: assume that, despite the tough talk, whenever another country stood up to him, Trump always chickened out. The “TACO trade” became an instant hit among those looking to profit. It also coined a phrase that revealed a deeper truth about Trump: behind the bluster, he is an insecure coward.
When it came to dealing with Trump, foreign governments were onto something. Now, it seems their approach may serve as a roadmap for his domestic political opponents. In recent weeks, Illinois Gov. JB Pritzker has refused to back down as Trump threatens to deploy the U.S. military to the streets of Chicago.
Pritzker flatly rejected Trump’s “crime-fighting” rationale and called it what it was — dictatorship. Counterintuitively, instead of de-escalating the rhetoric, Pritzker escalated it, raising the political stakes for Trump. So far, that strategy has proven successful, and it may ultimately be studied as a template for others in government and the private sector.
Like most bullies, Trump surrounds himself with weak sycophants. He values incompetence and loyalty over expertise and original thought. Defense Secretary Pete Hegseth is a fool. Secretary of State Marco Rubio and Attorney General Pam Bondi compete for the title of most obsequious. FBI Director Kash Patel wears the permanent expression of a small child lost in a shopping mall searching for his mother.
Since taking office, Trump has picked fights with people and institutions he assumed would back down or compromise. He attacked large law firms, and quickly discovered that many who marketed themselves as fierce advocates were all too willing to become his lapdogs. But when four firms stood their ground and beat him in court, he abandoned his efforts to compromise the legal profession further.
He made the legacy media his permanent punching bag because, with a few exceptions, it bent to his will. Media companies have paid millions in bogus settlements and repeatedly allowed Trump to dictate the terms of coverage of his administration.
He also racked up settlements against universities — until Harvard stood its ground. Since then, his attacks on higher education have been more muted, as he reportedly seeks any settlement he can spin as a win.
Most recently, Trump has tried this strategy against large urban centers. He loudly deployed the National Guard and U.S. Marines in Los Angeles, followed by an even more grandiose deployment in Washington, D.C. In both cases, he used speed and his bully pulpit to shape the political reality of improper domestic military interventions.
In early August, Trump suggested Chicago might be next after Washington, D.C. He has long spread lies about crime in the city. While claiming crime was at “record levels,” the truth is that rates have dropped this year: homicides down nearly 30%, robberies down 35%, and shootings down 40%.
Trump repeatedly directed threats at the Windy City throughout August and early September, even posting on social media that “Chicago is about to find out why it’s called the Department of WAR.”
Most leaders confronting Trump have tried to extend partial olive branches to appear reasonable and willing to compromise. Pritzker took a very different approach: he denounced Trump’s efforts outright.
For example, in late August, when Trump suggested deploying troops to Chicago, Pritzker responded:
“There is no emergency in Chicago that calls for armed military intervention. What President Trump is doing is unprecedented and unwarranted. It is illegal. It is unconstitutional. And it is un-American. This is not about fighting crime. This is about the President and his complicit lackey, Stephen Miller, searching for ways to circumvent our democracy, militarize our cities, and end elections.”
When the administration floated using the Labor Day holiday to quietly send in National Guardsmen from Texas, Pritzker again raised the stakes rather than de-escalating:
“None of this is about fighting crime or making Chicago safer. None of it. For Trump, it’s about testing his power and producing a political drama to cover up for his corruption.”
Days later, when Trump posted about “WAR,” Pritzker again fired back on social media:
“The President of the United States is threatening to go to war with an American city. This is not a joke. This is not normal. Donald Trump isn’t a strongman—he’s a scared man. Illinois won’t be intimidated by a wannabe dictator.”
Throughout this battle, Pritzker refused to accept Trump’s framing of the issue as law enforcement and crime. Each time Trump tried to make military deployment seem ordinary, Pritzker highlighted its extraordinary nature.
When Trump suggested the military would assist policing, Pritzker called it “armed military intervention.” When Trump claimed it was routine, Pritzker called it “illegal,” “unconstitutional” and “un-American.” Most importantly, when Trump claimed it was about safety, Pritzker made clear it was about dictatorship.
We all know what happened next: Trump retreated. Instead of Chicago, he landed on sending troops to Memphis — a city in a Republican-led state.
I have no illusions that this marks the end of Trump’s attempts to deploy the military in Democratic-led states. Persistence — and a willingness to ignore defeats — are among his greatest political skills. His administration has proven capable of responding to setbacks with even more aggressive tactics.
But for now, Pritzker’s approach has worked. And it stands as an example others can learn from and follow in the months and years ahead.
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