Bifnot won a red monkey in the Around Four Arches - Cutter Race of October 2004 on Midnight. Bifnot served as king of The Jolly Company for a long period, and was the first pirate to drop a war chest, making a claim for Emperor Island. Bifnot is a notable blockade navigator, and compiled the most comprehensive blockade strategy guide on navigation and board tactics to date, considered by many to be the gold standard for blockade navigation training.