Jeff approached Brandon Walsh in the hallway of West Beverly Hills High School and offered to book him some action on sports. Brandon, having dug himself into a hole with Duke Weatherill, placed a bet with Jeff to cover his costs.
After Brandon won the bet, Jeff told him that he didn't have the money. Brandon became enraged, slamming Jeff against the wall and threatening to break every bone in his body if he didn't pay up. Steve Sanders arrived to pull Brandon off of Jeff. Jeff later paid Brandon $200 dollars and told the rest would be coming.