(CNN) When Donald Trump accepted the Republican nomination for president in 2016, a little-known businessperson received a prime convention speaking slot just minutes before the nominee: Tom Barrack.
"I'm here because Donald Trump is one of my closest friends for 40 years," Barrack told the crowd in Cleveland, beaming about the "amazing" things he had to say about Trump.
Last week, Barrack became only the latest in a long line of Trump advisers, aides, employees and friends to be indicted since Trump won the presidency. Barrack was charged Tuesday with illegal foreign lobbying on behalf of the United Arab Emirates, accused by prosecutors of trying to influence the foreign policy positions of both the Trump presidential campaign and his administration.
Barrack and Trump's relationship dates back to Trump's ill-fated purchase of the Plaza Hotel in New York in the 1980s, and they remained close business partners in the succeeding years.
The founder of real estate and investment firm Colony Capital, Barrack played a significant role at several key points of Trump's campaign, helping to recommend Paul Manafort -- later convicted in special counsel Robert Mueller's investigation -- for a key role in Trump's campaign. Barrack later served as chairman of Trump's inaugural committee.
Barrack spoke out frequently as an adviser to Trump and a defender of the President, publicly pushing back when allegations surfaced involving Manafort's ties to Russia. Now Barrack is accused of using his access to Trump in an effort to lobby the former President on behalf of a foreign country.
Barrack was ordered released from jail on Friday on a bail package that includes a $250 million bond, and he will be arraigned in Brooklyn on Monday. He has denied any wrongdoing and a spokesperson has said he intends to plead not guilty.
But while Trump has come to the aid of many of his associates in trouble with the law, it's unclear if he'll do the same for Barrack.
Trump and Barrack remained close as Trump entered the White House, but their relationship has waned in recent years, according to sources familiar with the matter. Barrack has been under scrutiny since 2019, when the federal investigation into his work on behalf of the UAE was publicly disclosed, as was an investigation by the Washington, DC, attorney general into the Trump inaugural committee.
Barrack now joins a list of Trump officials charged by federal prosecutors that includes Manafort, Trump's longtime friend and adviser Roger Stone, former attorney Michael Cohen, first national security adviser Michael Flynn and former senior aide Steve Bannon.
Earlier this month, New York prosecutors charged the Trump Organization and its chief financial officer, Allen Weisselberg, with a 15-year alleged tax fraud scheme. Both have pleaded not guilty.
Before he left the White House, Trump pardoned Manafort, Stone and Flynn -- who had been wrapped up in the Mueller investigation -- as well as Bannon, who was accused of defrauding donors and was pardoned before going to trial.
When the charges were unsealed against the Trump Organization and Weisselberg earlier this month, Trump issued a statement attacking the probe as a "political Witch Hunt by the Radical Left Democrats, with New York now taking over the assignment."
But the former President, who has been issuing numerous statements each day on an array of topics, has been silent on Barrack's charges.
There's a paper trail of FBI interviews during the Mueller investigation, depositions, court documents and congressional reports that offer a window into Trump and Barrack's relationship as Trump went from real estate magnate to presidential candidate to commander in chief.
It also reveals how prosecutors alleged Barrack used his proximity to Trump to advance foreign interests of the UAE without disclosing his foreign lobbying, according to the indictment unsealed last week charging Barrack and two others, his employee Matthew Grimes of Aspen, Colorado, and Rashid Sultan Rashid Al Malik Alshahhi, a UAE national.
Barrack has also faced scrutiny connected to investigations into Trump's inaugural committee, though the indictment is unrelated to that probe. But he sat for a deposition with the District of Columbia attorney general in November, after the presidential election, as part of the investigation into alleged misuse of funds by Trump's Presidential inaugural committee.
Barrack testified that he wasn't interested in participating in Trump's administration, but he became involved in the inaugural committee to help Trump with the "go-forward process of what was on his agenda."
Barrack testified he's known the Trump family since 1985 and had relationship with Trump, his wife Melania and Trump's four adult children.
"Donald Trump is President of the United States, so an active friendship has become some, somewhat more complex," Barrack testified in November. "But yes, I do consider him a close friend, yes."
Barrack was one of dozens of Trump allies who got caught up in the special counsel probe. Witnesses were asked about Barrack's proximity to Trump and his foreign contacts. When Mueller's team interviewed him in 2017, members asked about some of the topics that ended up in his indictment.
FBI memos from Mueller witness interviews, previously obtained by CNN, show how Barrack used his friendship with Trump to help others but also to promote his secret foreign interests.
Barrack lobbied Trump "for some time" to hire Manafort as a campaign adviser in 2016, and arranged for Manafort to meet with Trump and senior campaign staffers at Mar-a-Lago, according to testimony from Manafort's deputy Rick Gates, who later worked with Barrack on Trump's inauguration committee and also worked for Barrack's investment firm.
Manafort got the job soon after the Mar-a-Lago meeting.
According to the FBI memos, Barrack told Mueller's team that Manafort sent him an early draft of a speech Trump planned to give about US energy policy in May 2016. He said he sent back some edits and suggestions, but his ideas were discarded. He also said he perceived the Trump campaign to have a negative view of the Persian Gulf countries, which included the UAE.
But Barrack apparently didn't tell Mueller that, according to his indictment; he backchanneled with Emirati officials regarding the speech. Prosecutors said he wanted Trump to praise Emirati leaders by name, among other things. His exact edits weren't in the final speech, but the indictment says his alleged Emirati handlers were thrilled that Trump touted "our Gulf allies."
The FBI memos also reveal what Barrack thought of some of Trump's controversial moves as president.
Gates told investigators that he was with Barrack in Washington when Trump unexpectedly fired then-FBI Director James Comey in May 2017, and that they agreed it was "typical Trump behavior to react without waiting for all the facts," according to the FBI memos.
Barrack came under new scrutiny in 2019 when Democrats on the House Oversight Committee accused Barrack of leveraging his connections to the Trump administration to push a business deal involving the transfer of US nuclear technology to Saudi Arabia while, at times, standing to profit from the proposal.
The Democratic report zeroed in on Barrack's alleged advocacy within the Trump administration for a Saudi Arabian nuclear technology deal. The House Democratic report included a text -- referenced in the Justice Department indictment-- of Barrack claiming that Trump had offered him a foreign policy role in the Middle East.
In the indictment unsealed last week, prosecutors allege that Barrack and Grimes helped UAE officials gain access to the Trump administration, and that Barrack was in touch directly and indirectly with senior Emirati officials.
Barrack and Grimes helped set up a phone call between Trump and an unnamed Emirati official in the first month of Trump's presidency, according to the indictment, and then advocated for appointing officials to the Trump administration favored by the UAE, including Barrack himself.
Barrack wrote in a text message that his appointment as either ambassador to the UAE or Middle East envoy "would give ABU DHABI more power!"
Prosecutors wrote that after the UAE and other Gulf countries severed ties with Qatar in 2017, Barrack's assistant requested to speak with Trump because he had "something very important to share...about the Middle East."
CNN reported last week that prosecutors had enough evidence to charge Barrack last year, but held off doing so until the arrival of a new administration, according to people briefed on the matter.
Democrats, who have accused Trump and former Attorney General William Barr of using the Justice Department to protect Trump and his allies, are now calling for an inspector general investigation into whether Barrack and others were given "special treatment by the Department of Justice during the last Administration, and whether his case was inappropriately suppressed."