The Supreme Court just handed President Trump a rare defeat in his push to secure Chicago’s streets.

In a stunning decision on December 23, the highest court in the land denied Trump’s request to send roughly 300 National Guard troops to protect Immigration and Customs Enforcement (ICE) agents in the Windy City, marking a significant check on presidential power, the New York Post reported. 

Let’s rewind to August 2025, when Trump first started eyeing National Guard deployments to cities like Portland and Memphis, only to hit legal roadblocks at every turn.

Trump’s Push for Federal Muscle

Undeterred, Trump turned his focus to Chicago, arguing that federal law enforcement needed backup amid what his legal team called “dangerous and chaotic” conditions.

“Conditions for federal immigration agents on the streets of Chicago remain dangerous and chaotic,” Trump’s legal team insisted. Well, that may be true, but the Supreme Court wasn’t buying the argument that this justified federalizing the Guard.

Last week, Trump took his case to the Supreme Court, hoping to overturn lower court rulings—and an appeals court affirmation—that blocked the deployment.

Court Draws a Hard Line

The justices, however, stood firm, ruling that the law Trump cited, which allows taking over the Guard when “regular forces” can’t execute the law, doesn’t apply here.

The majority opinion clarified that “regular forces” means the military, not federal officers like ICE agents, and thus the statute likely only kicks in when the military itself can legally step up.

In essence, the Court said Trump overreached, a rare slap on the wrist for a president who’s often sailed through the Supreme Court’s motions docket with ease.

Conservative Justices Split on Ruling

Conservative Justices Clarence Thomas, Samuel Alito, and Neil Gorsuch dissented, clearly seeing more wiggle room for Trump’s authority than the majority did.

Justice Brett Kavanaugh, while siding with the majority, offered a narrower concurrence, hinting at future concerns. “The court’s legal interpretation, as I understand it, could lead to potentially significant implications for future crises that we cannot now foresee,” he warned. That’s a polite way of saying this ruling might handcuff leaders when the chips are down.

Meanwhile, the White House tried to shrug off the loss, with spokeswoman Abigail Jackson asserting that Trump’s core mission to protect federal personnel remains intact.

Broader Context of Guard Deployments

Let’s not forget Trump has managed to station troops in Washington, D.C., since August 2025, though even that move is under legal scrutiny by a federal judge.

Unlike other cities, the federal government holds more sway over D.C., which might explain why that deployment stuck— for now.

Still, this Chicago ruling is the Supreme Court’s first direct weigh-in on Trump’s broader strategy to send the Guard to urban hot spots, and it’s a clear signal that judicial patience for such moves has limits, even among a Court often friendly to his agenda.