Ring-a-Ding-Ding!: Swank is met by the Courier upon entry into the Tops casino. The player character can make Swank aware of Benny's plans through a series of Speech checks (15, 30 and 45) and is then allowed to progress to Benny's suite with all the player character's weapons. The player character only needs to pass the first two Speech checks to gain access to their weapons.
Proof can also be found along the way such as Benny's lighter, and distinctive cigarettes, along with other proof that can sway Swank.
Effects of player's actions
If the Courier opts to kill Benny in Ring-a-Ding-Ding!, Swank can later be heard "consoling mourners" in an interview with Radio New Vegas by saying, "If I know my pal Benny he's swinging with the big cat upstairs as we speak, or chasing some angel broad with cans as big as her halo." However, if the player character has shown evidence to Swank that Benny attempted to kill the Courier, he will state in conversation he "guesses he's the boss now." He, along with everyone else in the Tops, will mention how he "thought Benny was a stand up guy" and that he never saw him as a rat.
If the Courier kills Swank, they will be allowed to enter the Tops casino with all of their weapons.
If the player character convinces Swank that Benny is planning something behind Mr. House's back, Swank asks the Courier what they want to do. If the player character says they want to take Benny out now, Swank will send Benny to his room. There the Courier can kill Benny. Afterwards if the player character returns to Swank he will ask,"Has Benny been dealt with yet?" There is only one speech option as "Yes he is dead." Swank seems to rejoice this fact by commenting, "Guess that makes me the boss. Ring-a-ding!".
If the player character has the Black Widow perk and asks Swank about work, she can convince him to give her 100 caps to "buy something pretty."
In his appearances, he wears three different suits: black in All Roads, gray on his playing card and dirty white in Fallout: New Vegas. (Because he's wearing a grimy pre-War businesswear, which is white due to a texture error, it can be said he wears black in the base game.)
If the player character convinces Swank to let them keep their weapons to deal with Benny, if they return at a later time, after Benny's death, he'll greet the player character with a hostile attitude if they talk to him such as, "Give us a good reason not to fill you with lead!", although he won't turn hostile.
The quote mentioned above will go away once the Courier has done notable deeds, such as killing or disabling Mr. House, and eventually, that will go away as well, then permanently saying, "Something else you need?"
"Don't get me wrong, that resort of theirs is ring-a-ding, but my guts say, "Don't go in the basement.""
"Man, we're only the coolest cats on the whole Strip. We been here the longest, we got the swankiest digs, and we got caps rolling in like the tide. Everybody loves the Chairmen, because we show them a simple good time, no strings attached."
"Oh, boy, those clowns. Listen up, kid, and listen good, I don't care how many fancy Latin names he gives himself, a thug ain't nothin' but a thug. Warlords and emperors? Don't make me laugh. At least they got enough brains to stay the hell out of New Vegas - Mr. House'd clean their clocks."