Kleinfeld, who stole $1 million in payoff money from his client, Mafia boss Anthony Taglialucci, is coerced into providing his yacht to help Taglialucci break out of the Rikers Island prison barge. Kleinfeld begs for Carlito's assistance in the prison break, and Carlito reluctantly agrees. That night, Carlito, Kleinfeld, and Taglialucci's son, Frankie, sail to a floating buoy outside of the barge where Taglialucci is waiting. As they pull Taglialucci aboard, Kleinfeld kills him and Frankie and dumps their bodies in the East River. Carlito immediately severs his ties with Kleinfeld and decides to leave town with Gail. The next day, Kleinfeld barely survives a retaliatory assassination attempt at his office.