Former President Donald Trump has retained who knows how many lawyers in a truly mind-boggling number of cases since he announced his run for president in 2015. And while he has at times begrudgingly accepted their counsel, Trump is keeping only the most pliable of those attorneys around to represent him.
In the Mar-a-Lago documents case, especially, as is his nature, he’s refusing to listen to any counsel who says anything contrary to what he wants to hear. And it’s costing him dearly — both in money and in continued legal exposure as he takes his legal battle against the Justice Department to the Supreme Court.
It appears that, for the most part, the lawyers Trump has retained in his post-presidency have been acceding to his demands, no matter how ridiculous or personally damaging. (See: the ridiculous defamation suit filed against CNN this week.) At least one of them could face legal jeopardy for having signed off on official documents saying Trump, who’d squirreled away documents, had fully responded to a subpoena demanding their return when he hadn’t.
The Washington Post reported Monday that at least one of his lawyers, Alex Cannon, tried to push back against Trump’s orders. In February, after the first cache of documents had been handed over, Trump wanted a statement he’d dictated to be released, which claimed that he had returned “everything” that was requested, the newspaper reported, and he wanted Cannon to send a similar message to the National Archives and Record Administration. Cannon, reportedly, didn’t think that was a good idea:
But Cannon, a former Trump Organization lawyer who worked for the campaign and for Trump after the presidency, told Trump he could not tell the archives all the requested material had been returned. He told others he was not sure if other documents were still at the club and would be uncomfortable making such a claim, the people familiar with the matter said. Other Trump advisers also encouraged Cannon not to make such a definitive statement, people familiar with the matter said.
Turns out Cannon was right to hold off on putting that claim in writing, given the discovery of hundreds of documents during the FBI’s search in August. By that point it was clear that Trump needed even more legal firepower, including someone with experience practicing in South Florida’s courts.
But given his general reputation for difficulty and not paying those who work for him, Trump has struggled harder than most rich people do to find qualified lawyers. When he finally managed last month to persuade former Florida Solicitor General Chris Kise to represent him in the Justice Department’s investigation, Kise demanded $3 million, paid upfront.
That money bought Trump one of the most coherent legal briefings his team has produced in years, filed to the 11th U.S. Circuit Court of Appeals. But since then, Kise had been quiet, and his name was missing from several subsequent filings in the case. CNN reported last week that he had been “sidelined” but that the “reason for the shift in Kise’s role remains unclear.”
The Post reported Friday that Kise was benched for daring to suggest that Trump try to cooperate with the Justice Department. “Federal authorities had searched Trump’s Florida residence and club because they badly wanted to retrieve the classified documents that remained there even after a federal subpoena, Kise argued,” according to The Post. “With that material back in government hands, maybe prosecutors could be persuaded to resolve the whole issue quietly.” Kise might have found a winning strategy, one that managed to prevent weeks, if not months, of litigation and potential criminal charges. But it’s one that goes against Trump’s combative instincts. All seemed to be forgiven by Tuesday, though, when Kise’s name appeared on an emergency appeal to the Supreme Court. The filing asked the justices to vacate the 11th Circuit’s order last month that allowed the FBI to continue reviewing roughly 100 documents with classification markings seized at Mar-a-Lago. Whether this latest argument from Trump’s lawyers will carry any water is secondary to the fact that they’ve done as their client has demanded and continued to fight. As we saw after the 2020 election, the Chris Kises and Alex Cannons of Trumpworld have always been drowned out by the Rudy Gulianis and Sidney Powells. Despite having no legal training, Trump is predisposed to listen to whichever voice in a room sounds most like his own. Reconciliation and noble defeat are anathema to these types, not when there’s even the most absurdly small chance of victory. In hoping for a deus ex machina reprieve from the Supreme Court, Trump, with his visceral need for escalation, has won out yet again.
Hayes Brown is a writer and editor for MS NOW. He focuses on politics and policymaking at the federal level, including Congress and the White House. 
