During June of 2008, Gregory was asked to leave after serving for over 30 years. Lehman shares had fallen 25% in a week, even though the firm had raised $6 billion in funding. He was one of Lehman's largest individual creditors, with a total claim of $233 million in deferred compensation. Since leaving Lehman, Gregory has been in the news for selling several of his properties and vehicles. He sold his prized helicopter that he used to fly from his Long Island home to Manhattan, and fired his household staff of 29. His Bridgehampton home, listed for $32.5 million, sold for $20 million to Donny Deutsch. He put his Lloyd Harbor, NY home on the market for $22 million.