The group urged Chutkan to reevaluate her order, calling it both vague and overbroad, with aspects of its meaning “unknown and perhaps unknowable.” One particular uncertainty the ACLU seized on was the meaning of Chutkan’s prohibition on statements that “target” Smith, his prosecutors, court personnel, defense attorneys or witnesses.

“Reading the order, Defendant cannot possibly know what he is permitted to say, and what he is not,” the group wrote.

Trump’s lawyers opposed the gag and have appealed to the D.C. Circuit Court of Appeals. Chutkan has temporarily lifted the gag order while she mulls a request to keep it on ice during that appeal.

Trump has also run into trouble in connection with a separate gag order issued by a judge in New York overseeing a civil case involving Trump’s business empire. After Trump used his social media platform to attack the judge’s law clerk, the New York judge ordered Trump not to make comments about court staff. Last week, Trump was fined $5,000 for violating that order, and he racked up another $10,000 fine Wednesday.

Chutkan said during a hearing on the gag order issue in her court earlier this month that Trump should not be treated differently from other defendants simply because he’s running for president. But the ACLU said the ongoing campaign heightens the public interest in letting the former president speak freely about his prosecution and other grievances against Smith’s office.

“Defendant’s ability to speak publicly about the substance of the prosecution, even including potential witnesses and testimony, is in many ways inextricable from the 2024 presidential campaign in which he is a declared candidate,” the ACLU brief said.

The ACLU brief also echoed arguments from Trump’s lawyers that his speech should not be curtailed simply because some who hear it may have acted violently or issued explicit threats to the targets of his ire.

“The First Amendment does not authorize the Court to impose a judicial gag order on Defendant merely because third parties who hear his public statements may behave badly of their own accord,” the group wrote.

Taking Trump’s side in court is a new look for the ACLU, which once boasted of filing more than 400 legal actions against the Trump administration and saw a huge influx of donations for its legal battles against Trump policies such as the travel ban.

Undoubtedly aware that many ACLU supporters will be surprised to see the organization coming to Trump’s defense, the group’s filing includes a blunt condemnation of his efforts to overturn the 2020 election.

“Defendant’s role in the events related to his obstruction of the peaceful transition of power are relevant not only to the proceedings in this Court, but to the country’s decision about whether he deserves to be elected again,” the organization’s brief says. “Much that he has said has been patently false and has caused great harm to countless individuals, as well as to the Republic itself. 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.”