Tom Barrack pleaded not guilty on Monday to charges that he acted as an unregistered agent of the United Arab Emirates and obstructed a federal investigation.

Barrack, a real estate investor who once owned the controlling stake in Miramax, was arrested last week and held for three days in a county detention center in San Bernardino. He was released Friday evening on a $250 million bond, and is required to wear an ankle monitor. The bond is secured by a $5 million cash deposit.

He appeared in person at federal court in Brooklyn on Monday. He is barred from traveling outside of New York, Southern California or Colorado.

Matthew Grimes, an employee of Barrack’s investment firm who was also indicted, also entered a not guilty plea.

Barrack has been friends with former President Donald Trump for decades and acted as an informal adviser on Middle East issues. Barrack, the founder and former CEO of Colony Capital, is accused of using his close ties with the Trump administration to advance the UAE’s foreign policy goals.

In a statement issued on Friday, Barrack thanked the jail staff in San Bernardino and praised their professionalism.

“I also want to recognize the grace and humanity of the gentlemen with whom I have shared a community over these last three days,” he said in the statement. “I am innocent and will prove that in court.”

Rashid Al-Malik, a UAE citizen, was also indicted on the foreign agent and conspiracy charges. He remains at large.

Barrack bought Miramax from Disney in 2010, in partnership with the Qatari state investment authority. He later sold the company to beIN Media Group, a Qatari broadcaster.