“Again, goal number one is to eliminate Mr. House and install my neuro-computational matrix on the Lucky 38's mainframe! Given how you're a new arrival, I also recommend that you get to know some of the region's tribes, so you can decide how you feel about them! By the time you've finished up all of that, the Legion should be close to attacking Hoover Dam and we'll execute the last phase of the plan!”— Yes Man
When the Courier first enters the casino, they can pass a Speech check with Swank, allowing them to enter with their weapons. Next, if the player character was able to pass the check and keep their weapons, go past the front desk across the casino floor and straight to Benny. Immediately, he will turn around and greet the player character, forcing a conversation with him. The player character will have many options when they first begin to converse.
The passive route is to follow the responses leading to Benny giving the player character the suite key and asking them to go up and wait in the room.
With a successful Speech check, the Courier can get him to lead them to the penthouse, which gives the option of killing him without his guards. The player character will then receive the Wild Card: Ace in the Hole quest, and can proceed to his personal suite, to meet Yes Man.
The other route is to directly attack him. He yells for help from his four bodyguards. Two of the guards will be carrying silenced submachine guns, the other two carry silenced .22 pistols and Benny is using Maria, a unique 9mm pistol.
If the Courier is female and has the Black Widow perk, they can convince Benny to have sex with them in his suite. Upon finishing, the Courier will have the option of murdering him in his sleep.
If the player character chooses the passive route, without Benny leading them, go straight up to the presidential suite. Once in the room, check around for clues, grab whatever items one needs and return to the door, where Benny will be on the intercom. With a high Speech skill, the player character can persuade him to give more information. Otherwise, the Courier will end up having to threaten him, then his guards will show up and attack.
Find the safe behind the counter and loot it. Once this is done, Yes Man should confront the Courier; talk to him to activate another quest.
Search Benny's room in the Tops for clues.
Talk to Yes Man about how to take over Vegas.
Behind the scenes
The phrase "ace in the hole" is used to describe something that can supply a sure victory when revealed. An old American slang (dating from before 1920s), it may have originated from five-card stud poker, in which one of the card in each player's hand is kept face down (in the hole) from being viewed by other players until showdown, thus not reviewing the strength of the hand until the end.