On a pursuit after a pirate who made off with his booty, Winslow was caught in the wind current of Flotsam Island where he presumably crashed into the reefs, stranding him on the island the same as all the other inhabitants of Flotsam. After a while living on Flotsam, Winslow became captain of the Screaming Narwhal after by tradition somehow knocking off the previous captain. Ever since then, he never leaves the Narwhal in fear that it may be taken from him, though he claims that no-one on the island has been brave enough to challenge him. At some point before being drawn into Flotsam Island, Winslow once journeyed round the Jerkbait Islands in the hold of Captain Liverbottom's trader ship, and served as a cabaña boy in Borneo. He also worked at and became a master of haiku in the Sashimi