The Billionaire Governor Taking on Trump (At His Own Expense)

What do you call a billionaire who campaigns to raise his own taxes?

In most contexts, you'd call them crazy. In Illinois, you call them Governor.

JB Pritzker spent $58 million of his own money in 2020 trying to pass a graduated income tax that would have cost him significantly more each year. Voters rejected it 55 to 45 percent. He still supports a national wealth tax. The Hyatt hotel fortune heir isn't just advocating for policies that would lighten his wallet—he's turned Illinois into ground zero for the most aggressive state-level resistance to Trump's second-term agenda.

While other blue-state governors have sought compromise or quiet resistance, Pritzker has gone full confrontation: limiting ICE operations, creating oversight commissions, filing federal lawsuits, and successfully blocking Trump's attempt to deploy federalized National Guard troops on Chicago's streets.

The Illinois Resistance Playbook

Pritzker's strategy is surprisingly practical. "Pull out your iPhone, pull out your Android phone, video everything," he tells residents facing ICE raids. "Not just the people being pursued, but neighbors who want to protect their neighbors."

That advice isn't theoretical. When Trump threatened to send National Guard troops to Chicago and Pritzker refused, Trump federalized Illinois's Guard. But here's what happened: those 300 troops never made it to Chicago's streets. Courts, including the Supreme Court, ruled Trump lacked authority to deploy them domestically. The troops stayed confined to federal bases.

The video evidence Pritzker encouraged residents to collect? It helped win court cases against ICE and CBP agents, he says.

"ICE and CBP today under Donald Trump are stopping US citizens who are Black and brown and demanding to see citizenship papers," Pritzker argues. "They're racially profiling."

The Democratic Immigration Dilemma

But here's where things get complicated. Democrats have historically funded and expanded ICE. As recently as 2024, Democratic presidential candidates acknowledged illegal immigration as a problem. Cities like Chicago have struggled with increased undocumented migration in recent years.

So what's the real difference between Democratic and Republican immigration enforcement? Is it just about tone—wanting deportations to happen quietly rather than publicly?

Pritzker draws a sharp line: "Donald Trump has turned them into a secret police." He doesn't just want reform—he wants ICE "wiped away and replaced" entirely. That puts him well to the left of most Democratic officials, including those who've voted to fund ICE operations.

When Self-Interest Meets Ideology

Pritzker's most fascinating contradiction is his wealth tax advocacy. Most billionaires don't campaign for policies that would cost them millions. Most wealthy Democrats quietly oppose wealth taxes while supporting other progressive causes.

Not Pritzker. "You've got to pay for roads. You got to pay for government. You got to pay for the supports that the most vulnerable need," he says. "The question is, who should that burden fall on? People who can't afford it or people who can?"

This isn't recent positioning. He's been consistent about progressive taxation throughout his political career, even when it costs him personally. Whether that reflects genuine conviction or sophisticated political calculation is an open question—but the consistency is notable.

The 2028 Question

Democratic strategist James Carville has publicly backed Pritzker for president in 2028. He's been traveling to New Hampshire. Illinois is pushing to move up in the Democratic primary calendar. The signs point in one direction.

Pritzker deflects: "I'm running for reelection. That is what I'm focused on." But he doesn't exactly shut the door. "I'm the governor of the fifth-largest state in the country. I'm very proud of that fact."

For a party searching for new leaders after electoral defeats, a billionaire governor who puts his money where his mouth is—literally—presents an intriguing profile.