The American Civil Liberties Union (ACLU) has long been a foe of former President Donald Trump, boasting in 2020 that it had launched 400 lawsuits against his administration.

Yet in a surprising move, the left-wing organization recently sided with Trump in one of his legal fights.  

ACLU files brief challenging gag order

According to The Hill, the ACLU filed a brief with U.S. District Judge Tanya Chutkan on Wednesday regarding a gag order she imposed on the former president earlier this month.

Fox News reported that Chutkan, who is presiding over Trump's criminal trial in Washington, D.C., issued limitations on what the former president can say at the urging of Special Counsel Jack Smith.

Specifically, the judge prohibited Trump from publicly going after any members of the prosecution team or court staff along with those who could foreseeably be witnesses, saying,  "No other criminal defendant would be allowed to do so, and I'm not going to allow it in this case."

That move didn't go over well with the ACLU, which argued that Chutkan's gag order was a violation of the Constitution's First Amendment.

"Trump retains a First Amendment right to speak"

"Former President, and now Defendant, Donald Trump has said many things," The Hill quoted the ACLU as acknowledging in its court filing.

"Much that he has said has been patently false and has caused great harm to countless individuals, as well as to the Republic itself," the document continues.

"Some of his words and actions have led him to this criminal indictment, which alleges grave wrongdoing in contempt of the peaceful transition of power," it asserts.

"But Trump retains a First Amendment right to speak, and the rest of us retain a right to hear what he has to say," the brief declares.

Trump threatened with jail time for New York gag order violation

It goes on to contend that the gag order is excessively vague as the former president "cannot possibly know" what he is or is not allowed to say.

"The entire order hinges on the meaning of the word 'target.' But that meaning is ambiguous, and fails to provide the fair warning that the Constitution demands, especially when, as here, it concerns a prior restraint on speech," it adds.

The Hill noted that Chutkan's gag order is not the only one Trump has contended with, as a similar order was imposed in his New York civil trial by Judge Arthur Engoron.

As Fox News explained, Engoron fined Trump last week and threatened him with jail time over a social media post and comments he made at a press conference.