Benny was a part of the tribal gang called the Boot Riders before Mr. House occupied Vegas. As one of the three tribes who acknowledged to House's new rule, the Boot Riders were allotted to modernize The Tops casino.
They were given suits and ties and renamed "The Chairmen". Benny saw the ability of New Vegas, but the tribe's chief at the time, Bingo, wanted to stay nomadic. To decide the direction of the tribe, Benny confronted Bingo to a knife fight, and the winner would be the leader of the tribe. Benny stabbed Bingo in the throat, killing him and winning the fight.
Benny is fast to eradicate dissent among those Chairmen who sustain the old ways, even killing an old friend, an unnamed singer with a Psycho overdose.