Mob Boss in a Fantasy World

The head of the family is someone who is responsible for taking care of the rest. Vincent Denaro has been leading his family since his father died. He's collected a lot of debts and earned a lot of favors. After his family is wiped out in a sudden betrayal, he decides to collect the debt he has with the ruler of death himself. Instead of granting him revenge though, Death sends him into the cycle of reincarnation with his memories. Follow him on his journey of bringing his family to the top! ... in a world with magic? and dragons?