The 100 Lives of Black Jack Savage

When Barry Tarberry, a Wall Street con artist as devious as he is wealthy, flees to the Caribbean to avoid facing trial for his misdeeds, he finds his tropical castle home inhabited by an otherworldly spirit. This spirit is that of Black Jack Savage, a famed pirate from the 17th century, who only Barry can see. Now, with his assets frozen by the government and an unwanted supernatural roommate, the two must work together to save 100 lives, or face divine punishment for their worldly sins. (Summary by SageSledge)