From trying to unilaterally reinterpret the plain language of the Constitution to attempting to usurp states’ authority over elections, President Donald Trump’s relentless, extreme attacks on our democracy have generated an avalanche of legal challenges over the past year.
That’s not an exaggeration. Democracy Docket is currently tracking hundreds of lawsuits related to the Trump administration’s illegal and authoritarian actions — and dozens of others are likely on the horizon.
If you’re struggling to keep up, we certainly can’t blame you. As we start 2026, here are the crucial legal challenges to Trump that we are watching closely in the new year.
Trump’s domestic military deployments
On the last day of 2025, Trump announced he was ending his National Guard deployment in Los Angeles and his attempted military takeovers in Chicago and Portland.
His retreat came just a week after the Supreme Court upheld a lower court ruling halting his efforts to send hundreds of Guard troops into Chicago, dealing a major blow to his effort to exert military control over cities and integrate soldiers into routine policing.
The court determined that Trump did not have the authority to invoke an archaic and rarely used law to federalize hundreds of Illinois Guard troops for the Windy City deployment.
The ruling — one of the court’s most significant rejections of the president’s agenda in 2025 — also undermined his Guard deployment in Los Angeles and his attempted intervention in Portland, both of which were also blocked by lower courts.
Nonetheless, Trump is unlikely to abandon his longstanding goal of using the military as a police force. In fact, in his announcement, Trump also threatened to return to major Democratic-led cities and states “in a much different and stronger form,” likely hinting at invoking the Insurrection Act.
One of the president’s most expansive emergency powers, the act allows the president to deploy the traditional military — such as members of the U.S. Army or Marines — and federalize state national guard troops in order to put down an insurrection or civil unrest.
The Supreme Court’s Chicago ruling did not affect Trump’s ongoing military intervention in Washington, D.C., or the deployment in Memphis, Tennessee that he extracted from Gov. Bill Lee (R). Both of those deployments were carried out under different laws.
Unlawful U.S. attorney appointments
Trump and Attorney General Pam Bondi have repeatedly used temporary appointments to circumvent the Senate confirmation process and keep loyalists atop key U.S. attorney offices across the country.
Several defendants succeeded in challenging many of those appointments last year. Most notable were former FBI Director James Comey’s and New York Attorney General Letitia James’ successful bids against Lindsey Halligan, who Trump tapped to personally bring criminal cases against Comey and James.
Challenges to Trump’s unlawful appointment are likely to continue, if not expand, this year. And as pressure continues to mount, several of his appointees, including Halligan, could be forced to resign.
Last month, Alina Habba became the first of Trump’s unlawful appointments to resign after an appeals court disqualified her from serving as New Jersey’s top federal prosecutor.
Their resignations should clear the way for judges in those federal districts to select a new U.S. attorney. However, Trump and Bondi have sought other ways to undermine U.S. attorney appointments, such as by dividing the powers of a U.S. attorney between multiple officials.
Where Trump takes his political prosecutions
Despite his prominent failures at waging lawfare last year, Trump’s revenge tour will almost certainly continue in 2026.
Though a judge tossed the Department of Justice’s (DOJ) first criminal cases against Comey and James, Trump’s prosecutors have continued to pursue them and will likely bring new trumped-up charges (pun intended) against other foes of the president.
And acting on two executive orders from Trump, the DOJ is also preparing to go after left-wing groups it deems responsible for domestic terrorism.
DOJ officials have claimed their chief concern is extremist violence. But security experts have warned that the department may be preparing to criminalize organized opposition to the Trump administration or create a pretext to target people or organizations that support progressive causes.
Moreover, in the final days of 2025, Bondi previewed the next dark turn in Trump’s retribution campaign. The DOJ, she said, is planning a mass prosecution of the president’s enemies through a vast conspiracy case in the Trump-friendly Southern District of Florida.
The fate of independent agencies
The Supreme Court is also considering whether to formally uphold Trump’s arbitrary dismissal of the last remaining Democratic commissioner on the Federal Trade Commission. In oral arguments last month, the court’s Republican-appointed majority appeared poised to side with Trump.
However, it remains to be seen how the conservative justices intend to do so without also turbocharging Trump’s effort to assert absolute control over independent agencies that regulate the economy, the stock market, federal campaign finance and communications.
During the hearing, several conservative justices raised the issue of “limits” on executive control, but did not articulate any clear vision of what that might look like.
At stake is a 90-year-old landmark Supreme Court case that allowed Congress to protect certain federal officials from arbitrary dismissals and paved the way for the modern U.S. administrative state.
Boasberg’s contempt probe
We’re also keeping a close eye on U.S. District Judge James Boasberg’s probe into whether Trump officials deliberately ignored court orders blocking flights of hundreds of people to a notorious Salvadoran megaprison.
Boasberg’s probe isn’t just consequential because it’s the first criminal contempt inquiry against the second Trump administration. Rather, Trump’s allies in the judiciary have also commandeered the investigation to embark on a dangerous effort to undermine courts’ inherent authority to investigate and punish contempt.
While pausing Boasberg’s probe last month, Trump appointees on the D.C. Circuit Appeals Court introduced a question about whether he has the power to investigate potential contempt or whether he must refer it to the DOJ, which would almost certainly ignore it.
Former DOJ officials and legal experts have warned that through this line of questioning, the Trump appointees could create a loophole through which the president and his subordinates can ignore court orders without fear of being held in contempt.