By Kaanita Iyer, Matt Stiles, CNN

(CNN) — Within weeks of retaking the White House, President Donald Trump boasted that he had “brought free speech back to America.” But since then, he has tested the limits of the First Amendment time and again, stoking alarm among civil rights experts and his critics.

The First Amendment protects the freedom of religion, speech and press; the right to peaceful assembly; and the right to “petition the government for a redress of grievances.” It also bars the government from enacting laws that prevent the “free exercise” of these rights.

Nonetheless, through executive orders, lawsuits and Truth Social posts, the Trump administration has gone after protesters, universities, news organizations, law firms and speakers it doesn’t agree with.

On Wednesday, the FBI searched the home of a Washington Post reporter, immediately setting off alarms among press freedom advocates who noted that Justice Department policies typically limit searches to extreme cases to avoid impairing public interest journalism.

Attorney General Pam Bondi said in a statement that the search was in connection with the “illegal leaks” of classified information from a Pentagon contractor. The reporter, Hannah Natanson, covers the federal workforce and has been a part of the Washington Post’s “most high-profile and sensitive coverage during the first year of the second Trump administration,” according to the outlet’s story on the search.

Several of the administration’s efforts have been successfully challenged in court. However, some organizations have also conceded to pressure from Trump, such as Disney’s ABC, which temporarily suspended Jimmy Kimmel’s show over his comments on Charlie Kirk after the conservative activist’s killing.

One civil liberties expert told CNN the First Amendment is “undoubtedly, unquestionably” being weakened.

The Trump administration is “trying to frighten Americans out of exercising their First Amendment rights by denying them benefits if they dare to do something that Trump doesn’t like,” said Burt Neuborne, a civil liberties professor at New York University law school.

Neuborne warned that the “net result” would be “a society that is not exercising their First Amendment rights. The First Amendment rights are there, but it’s too costly to exercise them.”

Here is a timeline of some of the instances where Trump has tested the First Amendment.

The-CNN-Wire
™ & © 2026 Cable News Network, Inc., a Warner Bros. Discovery Company. All rights reserved.