Jenoff ran a casino out of Los Angeles and had many individuals in his pocket, primarily from his side business in which he would procure requested items at the price of the requestor's soul. The payment was not required up-front, and the individual could live their life until either the merchandise (soul) were in jeopardy of being given to another, or if Mr. Jenoff decided it was time to collect.
Charles Gunn traded his soul to Jenoff for a truck in his early years of running The Crew, reasoning that his life would never really amount to anything and the truck could be useful in his mission to fight vampires. Later in his life Jenoff detected his love for Fred and immediately sent one of his henchmen to collect the soul early. Angel Investigations followed Gunn to the casino to back him up and Angel offered a double-or-nothing bet to Jenoff, putting not only Gunn's soul, but his own on the line. Losing the bet in a single-card draw, Angel chopped off Jenoff's head, only to be shocked when a new one started to grow. However, Angel took the opportunity to turn the crowd against Jenoff by asking if anyone else owed him anything, the entire casino ganging up on him at once and allowing the team to escape.