Jimbo is the unquestionable leader of the bullies, although he seems to be on par with Nelson, who has no interest for hierarchic systems. Jimbo is the tallest bully, and before it turned out that Kearney is actually 23, Jimbo was also considered to be the oldest of the gang. He was once beaten and bullied by Lisa Simpson. He is also the on & off boyfriend of Shauna Chalmers.
Jimbo is the abusive leader of the gang of bullies at Springfield Elementary consisting of himself, Kearney, Dolph and Nelson. He is extremely bossy, obnoxious, domineering, and bratty. He has mixed feelings with Bart, most of the time he will think he is cool but sometimes he will bully or tease him. While he may seem tough and dangerous, it is likely that he does this out of enjoyment to treat and hide his weaker, true self, as evidenced when threatened by a vengeful Moe.
When not bullying, he often can be found watching Soap Operas and drinking tea with his mother in their surprisingly lavish living room.
- In Treehouse of Horror V, Jimbo Jones is Principal Skinner's first victim, when Jones trips up Lunchlady Doris and her soup spills on Jimbo, Skinner notes it tastes nice and has Doris beat Jimbo to death then cook him up in the basement.