“I think that’s comical,” Gregorie said. “Here’s a guy from Palm Beach and he can find a lawyer in Washington, D.C., but in the busiest criminal district in the country, in the Southern District of Florida, he’s not able to find a lawyer? It’s almost funny.”
Appearing before a federal judge in Miami last week, De Oliveira, wearing a navy suit and glasses and without a local attorney, was unable to enter a plea.
It was a reprise of the two delays that led Walt Nauta, Trump’s personal aide who is also indicted in the classified documents case, to postpone entering his not guilty plea.
The district has no shortage of legal firepower, said Philip Reizenstein, a former Miami-Dade County prosecutor.
“We’re very active as defense attorneys,” Reizenstein said. “We don’t just roll over and plead guilty.”
Mark Schnapp, a veteran federal prosecutor who led the criminal division at the U.S. attorney’s office in Miami, said, “I don’t know what’s taking so long.” Schnapp said De Oliveira “had to know” he would be charged ahead of time.
Typically the government will contact targets to let them know they’re going to be charged and offer them opportunities to cooperate, former prosecutors said.
A source familiar with the matter said De Oliveira’s legal team was informed ahead of time that the government intended to seek an indictment. The source said the defense was offered a chance to explain why he should not face charges.
But even after the charges were announced in a superseding indictment and De Oliveira made his first court appearance, his defense team was still working to lock down local counsel.
“This is a delay tactic,” said Dave Aronberg, the state attorney in Palm Beach County. “I’ll walk outside in a couple of minutes. I’m going to trip over at least three lawyers who are admitted into the Southern District of Florida. You’ve got to watch your step.”
“This is a delay tactic. I’ll walk outside in a couple minutes. I’m going to trip over at least three lawyers who are admitted into the Southern District of Florida. You’ve got to watch your step.”
— Dave Aronberg, Palm Beach County, Florida, state attorney
Yet despite the historic challenge of wanting to represent a former president, veterans of the South Florida legal world who spoke to NBC News said other issues could be complicating the decision.
The cost of securing an attorney independent from Trump’s operation could prove a daunting challenge for workers targeted by federal investigators in the special counsel’s probes.
Gregorie pointed to potential conflicts with Trump, who promised to find De Oliveira an attorney, according to the updated indictment.
Trump’s Save America fundraising group spent at least $20 million on legal fees in the first half of the year, some of it with the firms of lawyers who have signed on to represent his employees, federal records show.
For De Oliveira, a former maintenance worker at Trump’s Mar-a-Lago estate accused with him and Nauta of conspiring to subvert federal investigators’ efforts to retrieve sensitive classified documents from Trump in his post-presidency, the stakes could not be higher.
Prosecutors allege that De Oliveira lied to the government by denying he had any knowledge of boxes of classified files, despite his role in moving them, and then tried to delete security video at the Palm Beach club after the Justice Department sought to obtain it. Trump called De Oliveira, and the two spoke for more than 20 minutes, according to the indictment.
He later approached another employee, identified as Yuscil Taveras, and informed him that “the boss” wanted the video deleted, prosecutors allege. That employee, who was once represented by a lawyer shared with another Trump defendant, sought new counsel last month.
De Oliveira, who is set to appear before the federal judge assigned to the case Thursday, faces a delicate path that could lead to new challenges down the line.
“This is a question of ‘how is this guy going to pay for his lawyer?’ And if he is being paid by Trump, that lawyer has got to say: ‘Listen, my job is to represent you. Some of the things I’m going to recommend to you may not be what Mr. Trump wants,’” Gregorie said. “That may be a real difficulty.”
Former prosecutors for the Southern District said lawyers face their own liabilities, including the financial peril of a defendant who loses the means to pay or the threat of landing in the very public crosshairs of Trump’s ire.
If a lawyer signs on to a case in Florida and the defendant stops paying, “you’re stuck,” Schnapp said.
Reizenstein said: “Unspoken among my colleagues who wanted to work for the president — within a group of certain people who were being consulted — [was] a cost-benefit analysis. Literally there were lawyers who were asking themselves how much is your reputation worth. Because a lot of people who take on the representation end up getting damaged themselves.”
“That was an undercurrent within the Miami legal community when he was looking for lawyers,” Reizenstein said of Trump.
Said Kendall Coffey, a former U.S. attorney for Southern Florida: “Lawyers associated with Donald Trump have had bad luck.”