Rattling Sabers: Trump’s Expanding War on Democracy

The entirety of Donald Trump’s second administration can be described as one continuous assault on democracy. Over the weekend, two new fronts have opened in this offensive: Illinois and Oregon. While legal challenges have been part and parcel of this war since the beginning, an interesting—and potentially alarming—development is the introduction of the actual military. Let’s look at what has transpired, and what might come next.

On September 27th, Donald Trump posted on Truth Social that he was directing Pete Hegseth to send troops into Portland. “I am also authorizing full force, if necessary,” he wrote. His justification? He characterized Portland as “war-ravaged” and claimed that ICE agents were under attack—a narrative that has become increasingly popular in the wake of the assassination of Charlie Kirk. At the time of this announcement, details of the deployment—including when it would take place—were not provided.

The next morning, Trump informed Oregon Governor Tina Kotek that he would be invoking Title 10, which authorizes 200 Guard members to perform federal duties for 60 days. Almost immediately after, both Oregon and the city of Portland filed a federal lawsuit against the Trump administration, arguing that the president lacked the authority to federalize the Guard in such a manner. “There is no insurrection or threat to public safety that necessitates military intervention in Portland or in any other city in our state,” Governor Kotek said in a statement later that day.

On Saturday, October 4th, U.S. District Judge Karen Immergut, appointed by Trump in 2019, issued a temporary restraining order (TRO) blocking Trump from activating Oregon’s National Guard. It wasn’t close, either. She called the idea that ICE facilities required National Guard assistance “simply untethered to the facts” and concluded, “Defendants have made a range of arguments that, if accepted, risk blurring the line between civil and military federal power—to the detriment of this nation.”

However, the ruling only affected Oregon National Guard service members. Thus, the administration quickly pivoted, attempting to deploy California’s National Guard to Portland instead—an apparent effort to bypass the injunction. “Mr. Hamilton, you are an officer of the court. Aren’t the defendants simply circumventing my order?” Immergut said in the hearing Sunday. Why involve California? Besides proximity, Trump had successfully federalized California’s National Guard during the Los Angeles protests earlier this year despite legal challenges. Round two didn’t go Trump’s way, however, as Immergut blocked the move in another, broader TRO issued in an emergency meeting on Sunday. This new order blocked any federalized National Guard deployments to Oregon until October 19th—a necessary step given the developments in Illinois.

The situation in Chicago is different—and arguably more alarming. In Portland, Trump’s team argued that National Guard assistance was needed, but Judge Immergut found that claim to be false based on law enforcement reports showing conditions had cooled since the summer. Chicago, by contrast, has been heating up for weeks. You may recall the “Chipocalypse Now” post, which was followed by a large-scale deportation operation, dubbed Operation Midway Blitz. This campaign has been public and aggressive—more so than usual for the Trump administration. Claims that ICE is disregarding the rights of both citizens and immigrants have become common—made worse by the administration’s insistence on turning enforcement into a social media spectacle.

And that was before last weekend. ICE conducted a “military-style” raid on an apartment complex; a Chicago lawmaker was handcuffed, removed from a hospital, and threatened with arrest; and a woman who allegedly “rammed” a law enforcement vehicle was shot—though witnesses contend the agents caused the crash. In the middle of this chaos, on Saturday, October 4th, Trump authorized 300 Illinois Guard members to deploy to Chicago to “protect federal officers and assets.” A day later, Texas Governor Greg Abbott also volunteered 400 of his state’s troops for deployment at Trump’s discretion.

On Monday, Illinois sued. “Among other things, Trump and Noem have sent a surge of SWAT-tactic trained federal agents to Illinois to use unprecedented, brute force tactics for civil immigration enforcement; federal agents have repeatedly shot chemical munitions at groups that included media and legal observers outside the Broadview facility; and dozens of masked, armed federal agents have paraded through downtown Chicago in a show of force and control,” the suit reads.

The arguments mirror those in the Portland lawsuit, but unlike Oregon, the judge did not issue a TRO. U.S. District Judge April Perry, a Biden appointee, said she needed time to review the government’s response and scheduled a hearing for Thursday. This delay poses a problem for Trump, who has little desire to wait, in a judicial setting or otherwise. On Monday night, he floated the idea of invoking the Insurrection Act, stating: “If I had to enact it, I’d do that. If people were being killed and courts were holding us up or governors or mayors were holding us up, sure, I’d do that. I mean, I want to make sure that people aren’t killed. We have to make sure that our cities are safe.” Later that evening, Abbott announced that the Texas National Guard was deploying and expected to arrive in Illinois soon (at the time of writing).

What Happens Next

Hearings are set for Illinois on October 9th and Oregon on the 17th, where courts will determine whether the TROs will be approved in Illinois and extended in Oregon. Officially, that’s where things stand.

Looking ahead, several scenarios emerge. Illinois is the more volatile situation. Reports from the weekend describe a marked escalation in ICE and federal law enforcement aggression. With roughly 700 troops expected to arrive in Chicago and tensions already high, there is a real risk of clashes in the next 24–48 hours—especially if those troops continue the pattern of escalation seen in recent days.

According to some, that may be exactly what Trump wants. Illinois Governor J.B. Pritzker has alleged that the administration is following a playbook “to cause chaos, create fear and confusion, make it seem like peaceful protesters are a mob by firing gas pellets and tear gas canisters at them. Why? To create the pretext for invoking the Insurrection Act so that he can send military troops to our city.”

Trump flirted with invoking the Insurrection Act back in 2020—you might remember the resulting photo op. That time, the act was never invoked, constrained by legal and political limits. But today, Trump’s leash is much longer, his control over the executive machinery much tighter, and the checks on his power far weaker. If he can produce even a sliver of plausible deniability before a sympathetic judge, he could well declare an “insurrection” and deploy troops at will.

What’s unfolding in Oregon and Illinois isn’t just a legal or political showdown—it’s a test of the system’s ability to restrain executive overreach. Trump’s moves reveal a pattern: escalate tension, provoke resistance, and then use that resistance as justification for greater force, regardless of the actual facts on the ground. Whether courts, governors, or ordinary citizens can hold that line will determine not only the fate of these two states, but the health of American democracy itself. If the past weeks are any indication, the defining struggle of Trump’s second term won’t be over policy or ideology—it will be over whether the rule of law can withstand a president determined to bend it to his will.