"Captain Pennies" (1910 - 1968) is the alias of the president of an S&L association based out of New Orleans, Louisiana. He possessed a clown fetish, and used an alias at brothels to disassociate his sexual tendencies from his public life. "Captain Pennies" was responsible for defrauding black and Irish people out of their life savings through phony investment schemes, all to finance his sexual escapades.
On 20 November 1932, while attending the University of Chicago for a business degree, "Captain Pennies" was present at the Corleone Hotel's brothel. He was tied to a chair as Salieri crime family soldato Tommy Angelo cleared the place of Chicago Morello goons, killed the manager Howard Davis, and planted a bomb in Davis' office as a message.
Thirty-six years later, after he became president at an S&L association in New Orleans, "Captain Pennies" was one of Marcano crime family associate Harry Robicheaux's three VIP guests at the Un Belle Jardin brothel, alongside Brother Superior and Neighbor Phil. He was killed by Lincoln Clay in order to damage Robicheaux's operations and force him out of hiding.