Former President Donald Trump will test the limits of his free speech rights Monday when he argues to a Washington, DC, appeals court that a gag order placed on him in his federal election subversion criminal case is not constitutionally sound. The high-stakes hearing before the US DC Circuit Court of Appeals will represent Trump’s latest bid to undo the gag order issued by a federal judge last month, an effort he says is necessary to defend himself outside the courtroom as he campaigns for a second term in the White House. The gag order from District Judge Tanya Chutkan restricts Trump’s ability to publicly target court personnel, potential witnesses, special counsel Jack Smith and his staff. Prosecutors argue such attacks could endanger some people close to the case. The appeals court has temporarily frozen the gag order as Trump continues to contest it. “The Gag Order violates President Trump’s most fundamental First Amendment rights. Even worse, it gives no consideration to the First Amendment rights of President Trump’s audience, the American public, to receive and listen to his speech,” Trump’s attorneys told the appeals court earlier this month. Legal experts have cast doubt on Trump’s argument, with Catherine Ross, a professor at the George Washington University Law School, saying she believes Trump’s appeal is meritless. “It is a foundational principle that First Amendment rights to speak may sometimes have to give way to the integrity of the judicial process and the importance of guaranteeing a fair trial,” Ross said. “This is a routine kind of limitation on criminal defendants,” Ross added. “It is more important to this discussion that he’s a criminal defendant than that he’s running for president.” This is the second Trump appeal of a gag order in the past week. The former president was recently under a gag order in the $250 million New York state civil fraud case. The judge overseeing that case barred Trump and his lawyers from making any statements about court staff, pointing to security risks. But on Thursday, an appeals court judge in the state temporarily lifted that gag order, saying the constitutional rights at issue gave rise to his decision to side, for now, with the former president. Both sides in Smith’s case will have the option of appealing the court’s decision to a panel comprised of all the judges on the DC Circuit or directly to the Supreme Court. The DC Circuit has considered a litany of Trump-related cases – particularly during his presidency – and the three-judge panel randomly selected to handle the gag order appeal includes two judges who have sided against Trump in recent years: Circuit Judges Patricia Millett and Cornelia Pillard, both of whom were appointed by former President Barack Obama. The third jurist on the panel – Circuit Judge Brad Garcia, an appointee of President Joe Biden – joined the bench earlier this year and has yet to hear a Trump-related case. Smith has brought four charges against Trump for his alleged efforts to remain in power after losing the 2020 election. The former president has pleaded not guilty and Chutkan has scheduled his trial for early March. First Amendment scrutiny Trump’s attorneys have mounted a constitutional challenge to the gag order, claiming that it violates a number of his rights – chief among them those guaranteed under the First Amendment. His legal team has asked the circuit judges to consider whether Chutkan’s restrictions run afoul of the free speech rights of “Trump and tens of millions of Americans to engage in and hear core political speech in the middle of an ongoing Presidential campaign.” The panel will also decide whether the gag order is “unconstitutionally vague,” with Trump’s lawyers arguing that it lacks “clear and precise language” needed to pass legal muster. “It restricts large amounts of core political speech that poses no plausible threat to the administration of justice,” Trump’s attorneys told the court in a filing. “The entire Gag Order rests on an unconstitutional ‘heckler’s veto’ theory, so it is overbroad in its entirety.” Trump’s arguments were not persuasive when he tried to have Chutkan pause the gag order while his appeal unfolded. In rejecting his request last month, the judge said that “the First Amendment rights of participants in criminal proceedings must yield, when necessary, to the orderly administration of justice.” Prosecutors, meanwhile, have consistently said that Trump’s attacks on individuals close to the case give rise to the restrictions on his speech. They told the appeals court last week that the Chutkan did not err when she issued the gag order and that the former president’s recent attacks on people close to the case while the order has been frozen are a reason his speech should be curtailed. “There has never been a criminal case in which a court has granted a defendant an unfettered right to try his case in the media, malign the prosecutor and his family, and … target specific witnesses with attacks on their character and credibility,” Smith’s team wrote in a filing. “The defendant has recently resumed targeting the Special Counsel’s family while the order has been administratively stayed,” they said. At a campaign rally earlier this month, Trump repeated several attacks on Smith, including with references to the special counsel’s family. The former president said Smith is “deranged” and a “Trump-hating prosecutor,” and that “his wife and family despise me much more than he does.” Referring to the alleged ill will Smith and his family have for Trump, the former president said that Smith is “about at 10” and his family is “about a 15 on a scale of 10.” Some major legal groups have raised concerns about the gag order, including the American Civil Liberties Union. “The entire order hinges on the meaning of the word ‘target,’” the ACLU wrote in a proposed court filing. “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.” Latest clash at the DC Circuit The DC Circuit has ruled against Trump in a number of cases both during and after his presidency, with Trump at times taking his losses straight to the Supreme Court for further review. In one of his more memorable cases before the appeals court, Trump lost a bid in 2021 to block records from his time in the White House from being released to the House select committee that investigated the January 6, 2021 attack on the US Capitol. In a unanimous opinion authored by Millett, the court said that what transpired on the day of the Capitol attack “exposed the fragility of those democratic institutions and traditions that we had perhaps come to take for granted” and said Trump had given no reason for the court to prevent the government from turning over the materials. The Supreme Court rejected Trump’s appeal. In two recent cases related to Smith’s pair of cases against Trump, the appeals court – in decisions joined by Judge Pillard – ruled in favor of positions that were potentially damaging to Trump’s cause. In one 2-1 ruling from late last month, the court upheld the Justice Department’s ability to prosecute January 6 rioters with an obstruction charge in a ruling that is likely to bolster their case against Trump, who has been charged under the same federal statute in Smith’s case. The other case involved Trump’s defense attorney Evan Corcoran, with the appeals court upholding a lower court order that said the lawyer must provide testimony to the grand jury that investigated classified documents found at Mar-a-Lago. The lower court made the decision after prosecutors with Smith’s office successfully argued that they had enough evidence that Trump’s interactions with Corcoran were part of a possible crime. Trump was later charged in the classified documents probe, where he has pleaded not guilty.