Tom Barrack, a billionaire investor and close friend of Donald Trump, was arrested on Tuesday afternoon for violating foreign lobbying laws, obstructing justice, and making false statements. Barrack is accused of illegally lobbying Trump on behalf of the United Arab Emirates between April 2016 and April 2018. He allegedly acted at the direction of senior Emirati officials.

But according to a seven-count indictment, Barrack never disclosed his lobbying relationship with the Emiratis, which is a violation of federal law. He also lied to the FBI about the matter, according to court documents. Penalties for violating the Foreign Agents Registration Act include up to five years of imprisonment.

Two co-defendants were also charged: Matthew Grimes, a former top executive at Barrack’s company, and Rashid al-Malik Alshahhi, an Emirati businessman.

“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 acting Assistant Attorney General Mark Lesko of the Justice Department’s National Security Division.

“The conduct alleged in the indictment is nothing short of a betrayal of those officials in the United States, including the former President,” Lesko said in a statement.

Barrack and Trump have been close for years. In 1988, Trump purchased The Plaza hotel from Barrack. The Washington Post expands on their relationship:

A real estate titan who became wealthy buying out-of-favor assets, Barrack was one of Trump’s closest associates during the campaign and in office, regularly speaking to the former president, visiting him and channeling him to others, including business officials and leaders in foreign countries.

He chaired Trump’s inaugural committee, which also faced federal investigation for its spending and activities, and at one point was considered as a candidate to become ambassador to Mexico.

The 74-year-old Barrack is accused of inserting talking points generated by the United Arab Emirates into Trump speeches. More from CNBC:

One of the events that caught their attention was a speech about energy policy that Trump gave as a candidate for president in May 2016. 

According to the indictment, Barrack “inserted language praising the UAE” into the speech, and “emailed an advance draft of the speech to Alshahhi for delivery to senior UAE officials.”

For the next two years, prosecutors allege, Barrack “sought and received direction and feedback, including talking points, from senior UAE officials in connection with national press appearances Barrack used to promote the interests of the UAE.”

Bloomberg points out that many Trump associates have landed in similar hot water:

Others tied to Trump have been charged with violations of the Foreign Agents Registration Act. Among them are former top fundraiser Elliott Broidy, former Trump campaign chairman Paul Manafort and former national security adviser Michael Flynn. Trump personal lawyer Rudy Giuliani is being investigated for breaches of FARA and has denied wrongdoing.