Thomas J. Barrack, a billionaire businessman and longtime friend to former president Donald Trump, was arrested Tuesday in California and charged with violating foreign lobbying laws, obstructing justice and making false statements, officials said.

He and two other defendants are accused of acting and conspiring to act as agents of the United Arab Emirates between April 2016 and April 2018, according to an indictment unsealed Tuesday afternoon.

Prosecutors allege Barrack, 74, used his decades-long relationship with Trump to lobby on behalf of the UAE without registering as a lobbyist or telling administration officials he was working on the country’s behalf. They also say he lied to FBI agents during a 2019 interview about his dealings with the wealthy Persian Gulf nation.

The 45-page indictment paints a portrait of a well-connected businessman devoted to advancing the UAE’s goals in the United States: trying to change the wording of a campaign speech, pushing for particular people to be hired in the new administration and aiding the UAE in its battle with regional rival Qatar.

Barrack, according to the indictment, helped schedule calls, draft statements, nix certain meetings and generally tried to push U.S. policy to be more favorable to the UAE, which he called the “home team” in one email to a co-defendant.

The charging documents do not claim that Barrack, who chaired Trump’s inaugural committee, was paid for his secret lobbying work. But a UAE sovereign wealth fund has invested significantly in Colony Capital, the investment firm Barrack founded and ran for years before he stepped down as executive chairman this year.

Also indicted and arrested Tuesday was Matthew Grimes, an employee at Colony Capital who authorities say reported directly to Barrack. A third man charged, Rashid Alshahhi, is a citizen of the UAE who lived in California until the FBI interviewed him about the case in 2018. Three days later, officials said, he fled the country.

Barrack and Grimes appeared in federal court in Los Angeles on Tuesday, where a judge ordered them to remain in custody for at least a few more days until their lawyers can present a set of bail conditions that prosecutors would accept. It is unclear whether they will be released before jail officials transfer them to New York, where the indictment was filed in federal court in Brooklyn.

“The defendants repeatedly capitalized on Barrack’s friendships and access to a candidate who was eventually elected president, high-ranking campaign and government officials, and the American media to advance the policy goals of a foreign government without disclosing their true allegiances,” said Mark Lesko, the acting head of the Justice Department’s national security division.

That alleged conduct, Lesko said, “is nothing short of a betrayal of those officials in the United States, including the former president. Through this indictment, we are putting everyone — regardless of their wealth or perceived political power — on notice that the Department of Justice will enforce the prohibition of this sort of undisclosed foreign influence.”

Barrack’s primary residence is in Los Angeles. His spokesman released a statement that said: “Mr. Barrack has made himself voluntarily available to investigators from the outset. He is not guilty and will be pleading not guilty.”

A lawyer for Grimes did not immediately respond to a message seeking comment. A lawyer for Alshahhi could not immediately be identified.

Officials said the lobbying effort began as Trump was sewing up the GOP primary nomination in the spring of 2016 and that Barrack “took steps to establish himself as the key communications channel for the United Arab Emirates to the campaign.”

A real estate mogul who became wealthy buying distressed assets, Barrack was one of Trump’s closest associates before and after the 2016 presidential election. He regularly spoke to the president, visiting him and channeling him to others, including business officials and foreign leaders, and at one point was considered as a candidate to become ambassador to Mexico.

“The defendant is charged with extremely serious offenses based on conduct that strikes at the very heart of our democracy,” prosecutors wrote in a court filing. Barrack, they said, “capitalized on his position of significant influence as an outside advisor to the Campaign and the Administration and as a national media figure with regularly televised interviews on major news networks to further the interests of the UAE as directed by senior UAE officials and their intermediaries.”

Barrack joins a long list of Trump friends, campaign associates and advisers who have faced criminal charges, including his former campaign chairman, Paul Manafort; the chief financial officer at his company, Allan Weisselberg; former Trump Organization lawyer Michael Cohen; former Trump White House strategist Stephen K. Bannon; and his former national security adviser Michael Flynn. Trump later pardoned some of those figures.

Trump’s inaugural committee, which Barrack chaired, also faced federal investigation for its spending and activities.

In a letter to the court, federal prosecutors called Barrack “an extremely wealthy and powerful individual with substantial ties to Lebanon, the UAE, and the Kingdom of Saudi Arabia” and contended that he “poses a serious flight risk” because of his “vast financial resources and access to a private aircraft on which he regularly travels internationally.”

They said Barrack has “deep and longstanding ties to countries that do not have extradition treaties with the United States.”

But the same letter also notes that prosecutors could envision a bail package for Barrack that imposes strict conditions for a release from custody.

Barrack helped rescue Trump’s business empire decades ago and was a top fundraiser for his campaign, though he declined to enter the administration. He was also a regular adviser on the Middle East, jetting through the region, voicing his opinions and talking with royalty and leaders as well as U.S. policymakers as he sought to boost Trump’s interest in the topic.

He was known in Washington as a consummate Trump insider familiar with the president’s mercurial moods, the ups and downs of the rotating cast of characters around him, and the vagaries of Trump’s policymaking process.

Barrack was sometimes consulted by Cabinet officials and others in the Trump White House on how to manage the president. He eventually grew frustrated with some of Trump’s conduct in office, however, and has told others that his advice regularly went unheeded.

After President Biden was elected, Barrack tried to persuade Trump to agree to an orderly transition but failed, The Washington Post has reported.