Benny

Benny is the head of the Chairmen of New Vegas in 2281. He is the brains behind a complex scheme to usurp control of New Vegas from Mr. House.

Background
Benny was a member of the tribal gang called the 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, and 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. Benny was challenged to a knife fight, the winner becoming leader of the tribe, and Benny walked away after putting a knife through Bingo's throat. Benny is cautious of the Chairmen who support the old ways, even killing an old friend, an unnamed singer with a Psycho overdose to stop dissent.

Benny's long-term goal is simple: control of New Vegas. The chances of such a thing happening seem slim, but as Benny himself would say, he's not done rigging the odds yet. After attacking 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 look at it in exchange for her reprogramming it. After finishing the reprogramming, the Securitron became Yes Man, an AI designed to obey every command given to him, which Benny used 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.

Quests

 * They Went That-a-Way: The Courier tracks Benny in an attempt to discover the purpose of the package and get revenge. Manny Vargas is the first person to give the player Benny's name, and where he went. Jessup in Boulder City will reveal that Benny betrayed his Great Khans followers after intercepting the Courier, traveling to New Vegas and leaving them to fend for themselves when cornered by the NCR.
 * The House Always Wins: House wants the Platinum Chip back in his possession. He needs you to recover it from Benny.
 * Ring-a-Ding-Ding!: The player must confront Benny at The Tops casino, which results either in Benny's death, or him escaping to Fortification Hill with the Platinum Chip in an attempt to activate House's secret weapon, where he gets captured by Caesar.
 * Render Unto Caesar: Benny is captured by Caesar, who offers the Courier a gift by allowing the Courier to choose how Benny dies. Benny, for his part, seems accepting of his impending death, and urges the Courier to take over his plan and create a truly independent New Vegas. Benny can be killed outright, be made to fight the Courier one-on-one inside the Arena, or crucified by the Legion (only the latter fate causes Benny to panic in any way, given its incredibly painful and torturous nature). Benny can also be untied by the Courier, at which point he will flee Caesar's tent and disappear from the game. Sparing Benny will cause Caesar and his Praetorian Guard to become hostile, leading to a very difficult fight. If you kill Benny (when he is tied up in the tent) before you take the quest, Caesar and his guards will become hostile towards you.

Other interactions

 * If the Courier is a female with the Black Widow perk, you can convince him to take you to his room, where you can either attack him or sleep with him. After some humorous dialogue, you are given the option to kill him quietly in his sleep or leave him be. He will not be present in the morning if you choose the second option.

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

Behind the scenes

 * A Benny is a trump card in trick-taking games, essentially a wild card, and is often represented by the Joker, Benny's card in the Collector's Edition deck.
 * At one point in development, the Chairmen were going to be called the Geckos, with Benny as the head of the Gecko family. However, this name was dropped from development and thus didn't make it into the retail-release of the game.
 * Benny is a reference to Benjamin "Bugsy" Siegel, who is often thought of as the father of modern-day Las Vegas. The similarities exist in the name and in Bugsy's trademark suit, which bears a striking similarity to Benny's, along with the fact that the two are very similar looking.

Bugs

 * If you choose 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. Yet you will not receive Maria twice it will only be on the Benny that is standing up next to the cross.
 * If the player 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 while in Caesar's tent when Benny is kneeling, you perform Ranger Takedown Benny will be knocked from his position on the floor, stand up and protest. Caesar and his guards will not protest or react even though "Benny is forbidden to speak under penalty of death", until you kill him, at which time one of the guards may praise the PC's fighting prowess immediately before attacking the The Courier.
 * If the player has the Super Slam perk, Ranger Takedown perk or a weapon that inflicts fatigue damage, it is possible to knock Benny off his cross. Upon landing, he will continue to act as if on the cross, but he will be standing on the ground.
 * If you choose to crucify Benny and kill him while he is crucified he can re-spawn if you kill Caesar and you can let him down for karma he will have his suit on but he will not have Maria.
 * If you have Benny come up to the presidential suite with you, and let him survive, he will move to the front of The Tops lobby. If you have 35 barter skill, you can then repeatedly choose (what do you have in mind?) and (The suite's a nice touch...), which will give you 500 caps and 250 The Tops chips every time. This bug allows for effectively infinite money.
 * When you talk to Benny at the first time in The Tops Casino, stand up in front of him and let him survive, and you can repeatedly choose the option dialogs between speech and barter skill. Speech will give you 60XP, and Barter will give you 500 caps, 250 The Tops chips and 35XP. This allows you get infinite XP and money and rise your level.
 * Sometimes after you talk to him in his suite, his bodygurds will not come in and attack you but if you rescued him from The Fort and talk 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.

Reference
Benny Бенни