Operating in Port Royal in Jamaica in the 1720s, Montanari was an infamous rumrunner and smuggler in the Caribbean, with a crew of two men and a donkey who helped transport cartloads of barrels. At some point in his career, he had befriended pirate Captain Jack Sparrow. In 1729, Montanari was found by Lieutenant Floyd of the East India Trading Company who had his men brutally beat Montanari to the point of unconsciousness. However, his crew were able to warn Jack Sparrow of the incident and the pirate intervened, quickly defeating the Royal Marines who were beating the defenseless Montanari and afterwards chasing Floyd down an alleyway and disposing of him. When Sparrow and blacksmith Will Turner came to check on the rumrunner, Montanari promptly had them smuggled into Fort Charles where they managed to rescue Capitaine Chevalle from the gallows in their attempt to rally the Pirate Lords. His further fate is unknown.