S3·E18 The Contender

Jack Roy, a fight promotor, tries to convince Sugar Duke, JJ's younger brother and a raising star in the boxing world, to leave his long time trainer, Vinny, for him and his big money before a big fight. While JJ stops by to see his brother in training, he also meets Jack Roy for the first time and is not convinced that Jack Roy really has Sugar Duke's best interest at heart. After JJ drops Vinny home, a couple of assailants mug Vinny. JJ is convinced that Jack Roy is behind this attack and asks Peter and the team to help. Apparently, Jack Roy's gambling interest takes precedent and wants Sugar Duke to throw the fight. He even goes out of his way to make clear that Sugar Duke's girlfriend will take a beating if Sugar Duke fails to. Alexander agrees that the team should help JJ and even throws in some resources to back the scheme up.