Jon Gabagooli is the leader of the Gabagooli criminal organisation and prisoner to Mr. Pickles for a time. Jon discovered the identity of Vito Pizzarelli (now "Bigfoot") after he was sighted at the grocery store. He confronted Tommy Goodman with two other crime bosses after Vito baked him a new fathers day pie. When they threatened his life, Vito came out of hiding and gave himself to their mercy. However, Mr. Pickles killed the other two crime bosses and brutally injured Jon to save Vito. He then took Jon to his lair and used him to help break into the grocery store to steal jumbo pickles.

Jon later escapes from Mr. Pickles' lair in season two by digging out of there, but was quickly arrested by the Sheriff when he was caught trying to steal a car. Jon's daughter, Lisa Gabagoolie, frees him from jail by seducing the Sheriff and stealing his keys. Under the false belief that the Sheriff had sex with her (thanks to Mr. Bojenkins taunting him in jail), Jon attempts to kill him until Mr. Bojenkins and the sheriff's mother come to the rescue. Jon and his daughter escape town in a car where they're confronted by what appears to be Mr. Pickles. Jon runs him over out of revenge, but discovers that it was actually a cardboard cut-out before the real Mr. Pickles rips his face off and shoots him in the mouth.