In 1938, Carbassa was trying to mooch drinks in the Coconut Lounge, Seacouver, when the newly arrived Duncan MacLeod offered to buy him a drink. The owner of Coconut Lounge, Sid Lankovsky, however, used the newcomer in a plot to kill his brother, Joey, and gunned down both his brother and MacLeod, claiming they had killed each other in an argument over the, singer, Peggy.
Benny's assigned Watcher in 1938 was Louie Panozzo, the doorman of the Coconut Lounge.
In 1995, Carbassa again met Sid Lankovsky, who had taken the name of Simon Lange, a respected citizen. In order to avoid a long time at the bottom of the Sound in cement shoes, Carbassa struck a deal with Sid: He would bring to him "the grandson of Duncan MacLeod," who talked about what happened that night in 1938 all of the time.
He lured MacLeod in the harbor, and clubbed him unconscious. Sid's men handcuffed MacLeod and threw him in the water. Benny arrived to fish him out the next morning. Benny's plan might have worked, if Duncan had not run into Lange that night at a charity event.
After MacLeod had taken care of things, Benny was ready to begin a new life. Duncan bought him a ticket to Chicago - a bus ticket.