Private equity billionaire and former Trump inaugural committee chairman Tom Barrack pleaded not guilty on Monday to federal charges that he illegally lobbied the White House on behalf of the United Arab Emirates while his longtime pal was president. As Barrack, 74, entered the Brooklyn courthouse, a protester outside hoisted a sign that read “DIRTY TRAITOR” and shouted, “It’s our democracy! It’s our democracy, not yours! Traitor! It’s our democracy, you asshole!”

A seven-count indictment accuses Barrack, 74, Aspen resident Matthew Grimes, 27, and UAE national Rashid Sultan Rashid Al Malik Alshahhi, 43, of “acting and conspiring to act as agents of the UAE” in an attempt to influence the policy positions of the Trump administration. Barrack, the founder of investment firm Colony Capital and a staunch Trump ally and friend, is also facing charges of obstruction of justice and making false statements. Barrack was released from jail last Friday after posting a $250 million bond, which was secured by $5 million in cash, some $21 million in securities, and Barrack’s California home. Prosecutors argued in a detention memo that Barrack was a “serious flight risk,” as he holds Lebanese citizenship and has access to a private jet.