The second-in-command of the Black Hats, Ulysses Boothe is a sky pirate of infamous repute. Recruited by Lucas Miles as his Sky Haven leader, Boothe set up and oversaw the small Black Hat base in that region until 1937, when the Fortune Hunters and the Black Swan arrived in Sky Haven, drawn by the stories of a new gang in town.
Seizing his opportunity, Boothe and his lackey Ace Dixon kidnapped the crews of both the Fortune Hunters and the Black Swan, imprisoning them aboard an abandoned cargo zeppelin. However, Nathan Zachary, leader of the Fortune Hunters, Sparks, his expert zeppelin pilot, and the Black Swan herself all avoided capture. On his next visit to the Cloud Nine Brothel, Boothe was attacked upon leaving by Zachary. With both pilots in Ford Hoplite gyrocoptors, it was a duel of pure skill - which Zachary handily won.
Zachary and the Black Swan then traded Boothe back to the Black Hats in exchange for the location of their crews. Despite an attempt by Ace Dixon to double-cross Zachary and the Black Swan, they were able to free their crews and exterminate the Black Hat operation in Sky Haven.