Background

• Benny turns out to be the head of the Chairmen of New Vegas, a faction that runs the Tops Casino. Benny plans to take over New Vegas from Mr. House, the President of the New Vegas Strip. Benny steals the Courier's package because it contains the Platinum Chip, a computer chip that controls the Securitron robots and opens several locked areas.
  
  

Killing Benny at Tops

• As part of the "Ring-a-Ding-Ding!" quest, you confront Benny at the Tops casino. You must convince Swank at the reception desk that Benny is guilty. You then get a key to Benny's room or the option to deal with him immediately. Killing Benny without his guards unlocks the "Wild Card: Ace in the Hole" quest. Directly attacking Benny results in a fight with his bodyguards. Female characters with the Black Widow perk can sleep with Benny and kill him in his sleep. In all cases, you can retrieve the Platinum Chip from Benny's corpse.
  
  

Letting Benny Live

• If you fail to kill Benny while fighting his body guards, ask Benny to spare your life, sleep with Benny and choose not to kill him or allow Benny to bribe you, he escapes and runs to Fortification Hill, still carrying the Platinum Chip. This hill, occupied by the Caesar's Legion faction, sports heavy fortifications as the name implies. You can reach the Fort by taking a barge from Cottonwood Cove.
  
  

Render Unto Caesar

• On arriving at Caesar's camp, you lose your weapons for the duration of your stay. Once you speak to Caesar, he will inform you that his men have captured Benny and that he has been sentenced to death. You get to choose how he will die and have the opportunity to speak to Benny. You can kill Benny outright, have him fight you in the Arena or sentence him to crucifixion by the Legion. You can also free Benny, at which point he disappears from the game, but this causes Caesar and the Legion to become hostile. Killing Benny instead of sentencing him also causes them to become hostile.
  
  

Benny's Suit

• Benny wears a black and white plaid suit that adds an extra five points to the Barter and Speech skills. You can pickpocket the suit from Benny if your skill is very high. Alternatively, you can strip the suit off Benny's corpse after killing him. A bug allows you to get two copies of the suit by first pickpocketing when you first enter the Tops, then killing Benny during "Render Unto Caesar."