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For comparison, Joe Biden lost just 13 similar cases across his entire four-year term.
On the day of his second inauguration, January 20, 2025, Donald Trump signed Executive Order 14149, with the title “Restoring Freedom of Speech and Ending Federal Censorship.”
The order bans the use of taxpayer resources to carry out what it claims has been censorship, which may refer to the efforts of social media platforms and independent researchers to mitigate or track misinformation.
The order also tells the Attorney General to investigate the federal government’s activities over the past four years in the context of free speech, and to seek remedial actions, although it is vague on what these actions may be.
The executive order closely aligns with a proposal released by the Trump campaign in 2022. In it, then-presidential candidate Trump vowed to sign the executive order banning any federal department from colluding with any business, person or organization, and to limit, categorize, censor or in other ways impede “the lawful speech of American citizens.”
So how has Trump’s fight for the freedom of speech gone a year and a half into his second term?
75 rulings of constitutional infringements
A recent review by Reuters uncovered 75 lower-court rulings finding that the administration infringed on constitutional freedoms. These cases involved rights to speech, religion, and the press.
“The President’s palpable misunderstanding that the government simply cannot seek retribution for speech he disdains poses a great threat to Americans’ freedom of speech,” Boston-based U.S. District Judge William Young wrote.
The administration has strongly rejected that criticism. White House spokeswoman Abigail Jackson argued that “the federal judiciary has repeatedly endangered and obstructed the election choices of the American people with its unlawful rulings.”
Defeats and victories
The legal battle lines stretch across numerous federal agencies and policy targets. Judges halted efforts to strip grants from major universities, including Harvard, over ideological disagreements.
Foreign students faced deportation over political advocacy, while legal firms saw their access to federal buildings suddenly revoked. U.S. District Judge Beryl Howell criticized an order targeting a prominent firm.
“Settling personal vendettas by targeting a disliked business or individual for punitive government action is not a legitimate use of the powers of the U.S. government or an American President,” Howell wrote.
Still, the White House has secured important wins on appeal. Higher courts overturned rulings that blocked the administration from stripping union bargaining powers from federal workers.
A rare record
Out of 93 First Amendment cases examined by Reuters, the administration lost nearly 80 percent. Democratic-appointed judges delivered most of those rulings, though Republican appointees ruled against the White House in ten cases.
By contrast, former President Joe Biden faced only 27 total constitutional challenges during his four years—losing less than half (13), with most centering on workplace vaccine rules..
Legal experts say the sheer volume of cases is historic. Law professor Timothy Zick noted that no president has pushed such broad speech restrictions since the Red Scare era under Woodrow Wilson.
