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In the early 2000s, Carlos De Oliveira was a valet and handyman at Mar-a-Lago, parking cars and doing odd jobs at Donald J. Trump’s private club and residence in Florida for not much more than $10,000 a year, court records show.
Then, within two months in 2012, Mr. De Oliveira divorced and filed for bankruptcy. He owned a 6-year-old BMW that needed brake work, paint and its belts replaced. His checking account, the records said, held $700.
But over a decade, Mr. De Oliveira, a Portuguese immigrant, started slowly climbing a ladder of promotions at Mar-a-Lago. First, Mr. Trump brought him on to the maintenance staff full-time, according to a person familiar with the matter. Early last year, he was given the loftier post of Mar-a-Lago’s property manager.
That was the job he held when he was named with Mr. Trump in a new indictment last week, one that accused him of conspiring with the former president and one of his personal aides to obstruct the government’s efforts to retrieve dozens of highly sensitive national security documents from Mr. Trump after he left office.
Mr. De Oliveira, a minor player in the case, was ensnared in it largely because prosecutors contend he delivered a message to another Trump employee that the former president wanted to delete a trove of potentially incriminating surveillance footage at Mar-a-Lago. He was also charged with lying to investigators.
The path he followed is a familiar one in the world of Mr. Trump, who often views relationships in terms of leverage and obsesses constantly about loyalty. In his business career, as a candidate and as president, Mr. Trump has frequently plucked subordinates from trouble or obscurity and given them a lifeline — and, by extension, a sense of obligation to him.
Those opportunities and obligations have sometimes come with a cost — including, as in the case of Mr. De Oliveira, serious legal jeopardy.
The release of new details on Thursday in an updated indictment by the special counsel, Jack Smith, underscored the extent to which low-level workers like Mr. De Oliveira — lacking Mr. Trump’s reserves of power, fame and money — have become embroiled in the government’s attempts to hold the former president accountable for threatening national security.
The situation is even more extraordinary because Mr. De Oliveira and Mr. Trump’s other co-defendant in the case, Walt Nauta, his personal aide, are relying on the former president not only for their paychecks but also their legal bills. Those are being handled by Save America PAC, one of Mr. Trump’s fund-raising entities.
A spokesman for Mr. Trump did not respond to a request for comment.
The payment of the legal bills has been the responsibility of Susie Wiles, one of Mr. Trump’s top political advisers.
She started by signing off on checks from the political action committee to lawyers for some of the former White House and campaign officials who received subpoenas in the past two years from the House select committee investigating Mr. Trump’s efforts to overturn the 2020 election. As the criminal investigations have unfolded, the number of lawyers whose payments Ms. Wiles is responsible for has grown.
Ms. Wiles also made an appearance in another portion of the indictment, where prosecutors described Mr. Trump showing a classified document to a representative of a political action committee — identified by people familiar with the matter as Ms. Wiles.
With so much of Mr. Trump’s past fund-raising spent on voluminous legal expenses, two people familiar with the matter said his advisers were creating a legal-defense fund to take on some of the costs, although the fund is not expected to cover the former president’s legal fees. It is unclear how many other people the fund is intended to support. Mr. Trump’s advisers have insisted there has been no effort to influence witness testimony through Save America’s payment of legal fees.
While Mr. Trump plays the leading role in the indictment in the documents case, the narrative as laid out by Mr. Smith’s team relies heavily on supporting characters like Mr. De Oliveira, Mr. Nauta and others.
Much of the story involves what prosecutors have said was a plot to move boxes of documents in and out of a storage room at Mar-a-Lago to avoid returning them to the government. Prosecutors say there was also a subsequent attempt to disguise those movements by seeking to delete footage from security cameras positioned outside the storage room.
According to the indictment, Mr. Nauta was central to the first part of the scheme, moving boxes from the room at least five times at Mr. Trump’s direction. All of that took place during a critical moment in the government’s investigation: the weeks between the issuance of a subpoena last year demanding the return of all classified documents in Mr. Trump’s possession and a visit to Mar-a-Lago shortly after by prosecutors seeking to collect the materials.
Mr. Nauta’s path to Mr. Trump and Mar-a-Lago was also characterized by a degree of turbulence.
A member of the Navy, Mr. Nauta had worked as a valet for Mr. Trump in the White House. But toward the end of his military career, Navy officials removed him from what is known as the Presidential Support Detail after learning he had fraternized with colleagues and subordinates in the White House mess, according to people with knowledge of the matter.
As naval officials were deciding what to do — including the possibility of sending Mr. Nauta back out to sea on a ship — an aide to Mr. Trump, who was already out of office, reached out to Mr. Nauta, offering him a job at Mar-a-Lago as the former president’s personal aide, according to a person familiar with the matter.
Mr. Nauta leaped at the opportunity, the person said, taking the job in July 2021 after receiving an honorable discharge from the Navy. It remains unclear whether Mr. Trump knew of Mr. Nauta’s troubles in the Navy at the end of his career.
Prosecutors say that they have been in touch with more than 80 witnesses while investigating Mr. Trump’s handling of classified documents, many of them low- to midlevel employees of Mar-a-Lago or the Trump Organization, the former president’s family real estate business. Most of these people — aides, assistants, housekeepers, security officials — have been interviewed by Mr. Smith’s team or appeared before grand juries.
Among them was Yuscil Taveras, who works for the Trump Organization in information technology and oversaw the surveillance cameras at Mar-a-Lago, according to people with knowledge of the matter. The indictment describes how in June 2022, on the same day that prosecutors issued a subpoena for footage from the cameras, Mr. Nauta and Mr. De Oliveira sent text messages to Mr. Taveras implying that they needed to speak with him.
A few days later, Mr. De Oliveira approached Mr. Taveras in Mar-a-Lago’s I.T. department and brought him to a private room for a conversation meant to “remain between the two of them.”
There, the indictment said, Mr. De Oliveira told Mr. Taveras that the “‘boss’ wanted the server deleted” — a reference to the computer server housing the footage. When Mr. Taveras responded that he did not know how to delete the server and did not think he had the right to do so, Mr. De Oliveira repeated the orders from “the boss,” according to the indictment. “What are we going to do?” Mr. De Oliveira asked.
Mr. Taveras, identified in the indictment as Trump Employee 4, provided the outlines of that encounter to the grand jury in May, the people with knowledge of the matter said. During Mr. Taveras’s grand jury testimony, prosecutors questioned him about his dealings with Mr. Nauta and Mr. De Oliveira, the people said, seemingly laying the groundwork for the indictment that was unsealed last week.
The Trump Organization ultimately turned over the surveillance tapes, and the indictment does not accuse any Mar-a-Lago employees of destroying the footage. (Mr. Taveras has not been accused of any wrongdoing. Although at one point Mr. Smith’s team was scrutinizing other aspects of his grand jury testimony, there is no indication he is facing legal jeopardy.)
At a trial, Mr. Taveras’s testimony could be crucial for Mr. Smith’s prosecutors in establishing a conspiracy to try to erase the tapes — and thus obstruct the investigation. And yet Mr. Taveras remains a Mar-a-Lago employee, one person with knowledge of the matter said. He has a new lawyer, and it is unclear who is paying his legal bills.
In a remarkable scene in the indictment, people in Mr. Trump’s orbit are described as beginning to worry about Mr. De Oliveira’s loyalties after the F.B.I. descended on Mar-a-Lago with a search warrant last summer and hauled away about 100 classified documents.
“Someone just wants to make sure Carlos is good,” the indictment quoted Mr. Nauta as saying to another Trump employee.
In response, that employee wrote in a Signal message with Mr. Nauta and Ms. Wiles that Mr. De Oliveira was “loyal,” according to prosecutors. It was unclear what, if anything, was said by others in the group message.
That same day, the indictment said, Mr. Trump called Mr. De Oliveira and said he would get him a lawyer.
Jonathan Swan, Adam Goldman and Kitty Bennett contributed reporting.
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