Benny

Benny is the head of the Chairmen

Background
Benny was a member of the tribal gang called the Mojave Boot-Riders before Mr. House took over Vegas. As one of the three tribes who agreed to House's new rule, the Boot Riders were assigned to renovate The Tops casino. They were given suits and ties and renamed "The Chairmen." Benny saw the potential of New Vegas, but the tribe's chief at the time, Bingo, wanted to stay nomadic. To determine the direction of the tribe, Bingo challenged Benny 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's long-term goal is to control New Vegas, and while the chances might be slim, he is not done rigging the odds yet. After disabling one of Mr. House's PDQ-88b Securitrons with a pulse grenade, Benny brought it in for examination. Unable to fix it himself, he allowed Emily Ortal to inspect it in exchange for her reprogramming it. After finishing the reprogramming, the Securitron became known as Yes Man, an AI designed to obey every command given to him. Benny used Yes Man's compliant nature to interrogate him on the details of House's machinations.

He learned Mr. House had something buried underneath the Fort and of the Platinum Chip - the key to all of House's plans. He also learned of the seven couriers hired by Victor - six decoys and one carrying the chip. Using Yes Man, Benny was able to discover the route the Courier would take, and hired Jessup, McMurphy and Chance to help him finish the job. The Courier was bound, gagged, shot in the head, buried in an unmarked grave at Goodsprings Cemetery, and left for dead.

After betraying his Great Khan accomplices, Benny made his way to the Tops and stayed in the casino area with four loyal bodyguards. Unbeknownst to him, the Courier was not dead... and his actions had not gone unnoticed by Mr. House either.

Appearances
Benny appears in Fallout: New Vegas and the graphic novel All Roads.

Behind the scenes

 * Benny is a Joker in the deck of Vault playing cards included with the Collector's Edition of Fallout: New Vegas.
 * Benny's appearance is a reference to Benjamin "Bugsy" Siegel.
 * Chris Avellone stated that "if there'd been time and the inclination, having Sunny Smiles, Yes Man, Benny, Vulpes, Victor and others as potential companions would have been great."

Bugs

 * If one chooses to crucify Benny, he will end up being crucified outside of The Fort. Sometimes, both the crucified and regular versions of Benny will appear, and the regular version can be killed for Maria. One cannot receive Maria twice; it will only be on the Benny that is standing up next to the cross. Talking to Benny next to the cross will result in you deciding to kill him again.
 * If one kills Benny before talking to him in his casino without getting noticed, the guards will continue to stand in their positions as if they were still protecting him.
 * If the player character has Benny come up to the presidential suite with them, and lets him survive, he will move to the front of The Tops lobby. With a barter skill of 35, one can then repeatedly choose (what do you have in mind?) and (The suite's a nice touch...), which will provide 500 caps and 250 The Tops chips every time.
 * Sometimes after talking to him in his suite, his bodyguards will not come in and attack, but if one rescued him from the Fort and talked to him back in his suite, after ending the conversation he will get up, walk out of the door and his guards will enter the suite. This bug also makes him disappear from the game completely.