Rafael's murder at the hands of drug lord Esteban Calderone (Miguel Piñero) led Tubbs to Miami, where he eventually teamed up with the Metro-Dade Organized Crime Bureau. Calderone was apprehended, but managed to bribe a judge to escape custody. Later, when trying to track the drug lord again, Tubbs sleeps with Angelina Madeira (Phanie Napoli), Calderone's daughter. Upon confronting the drug lord, Crockett and Tubbs are caught in a shoot-out, which ends when Crockett shoots Calderone dead. Several months later, Angelina surfaces again, having had a child as a result of her fling with Tubbs. However, her brother Orlando (John Leguizamo) has also located Tubbs, wanting revenge for his father's death. Tubbs' son, Ricardo Jr, is kidnapped, and Angelina killed, before Orlando escapes. Orlando reappears after luring Tubbs to a remote Caribbean island, hoping to trap and kill him. Tubbs is able to evade Orlando's gang, however, and escapes after killing his pursuer in a shoot-out.