Gregory aiming a gun at Darius. ("Tough Love")
Gregory Coleman was a loan shark and a known associate of the East River Crime Syndicate.
Late 2012, Gregory gives Darius Bishop a $100000 loan to open up a VIP lounge in his club. But when the club fails to turn a profit Darius became unable to pay the money back. Three months later, Gregory and his boss, Ray Scheckman, attacks Darius and then convince him to kill Heather Chandler. Vincent arrives just as Darius is about to kill Heather. Vincent jumps in between them and kills Darius before he could pull the trigger. Vincent then kills Gregory.