At Ops, Bashir announces that the creator of the program, Felix, installed Frankie as a "jack in the box," a sudden complication to shake things up and prevent the program from becoming boring. But he confirms that the problem can only be solved within the program using period-appropriate tactics. Feeling indebted to their "friend" Vic, Bashir, O'Brien, Nog, Kira, Odo and Ezri all agree to help. Even Kasidy joins in when she learns, but Sisko is mysteriously aloof to the whole idea, never having been interested in the Vic program.
The group gets together and plans a heist to steal the casino back from Frankie, who is financed by the kingpin Zemo. Kira plays the Honey Trap and seduces Frankie to distract him. Odo befriends Cheech using his shapeshifting and convinces him to hire Ezri as a cocktail waitress. Vic convinces Frankie to let him stick around on the promise to bring in a high-rolling gambler to the casino. As all of this goes down, Kasidy confronts Sisko on why he's so aloof to Vic. The captain finally admits that he finds the Politically Correct History in Vic's program distasteful, since it white-washes the fact that black people were still treated as second-class citizens in the 1960s. Kasidy argues that the program doesn't make people forget about history. Instead, it shows them how things ought to have been, where the only limitations are what they impose on themselves. Sisko is impressed by the speech.
The crew go over their plan. Kira will lure Frankie out of the casino to the bar. When one of the two money counters leaves to make a phone call, Ezri will have Bashir poison a martini with ipecac and deliver it to the lone money counter remaining. When he leaves to puke, Nog will slip inside and open the safe. Odo will transform from the cocktail tray and put all the money in a briefcase he makes out of himself. Kasidy will distract the guard by accusing O'Brien of stealing her money. Meanwhile, a high roller will win a bunch of money to further distract the gangsters on the casino floor. As if on cue, Sisko arrives to join in on the heist and takes the role of the high-roller.
It's the day of the heist, and Ezri accidentally drops her martini, but Bashir snags another drink from a nearby tray, and the heist continues. When she arrives in the money room but discovers that the normal counter has the day off and doesn't want a martini. She asks if she can drink it instead, and the man downs it out of spite. When Nog arrives to open the safe, he discovers that it has an auto-relock tumbler, which makes it much harder to crack. At the same time, Zeemo arrives and wants to inspect the vault. As Nog struggles to open the safe, Bashir shortstops the second moneylender to prevent him from returning and catching Nog. Vic accosts Zeemo's date to delay him but gets shooed away. As Nog finally opens the safe, Sisko and Bashir start throwing money around to cause a commotion and cover Nog and Odo's escape.
When Zeemo finally arrives in the money room, it's empty. Outraged, he has Frankie and Cheech escorted out, and the casino returns to normal. The gang all celebrate at the restored casino by listening to Vic sing. Sisko joins him on stage to perform a duet of "The Best Is Yet to Come," to the delight of the crew.
This episode provides examples of
- Artistic License History: Las Vegas was actually much more racially tolerant than Sisko believes. The Rat Pack helped desegregate casinos by refusing to play at any venue that wouldn't allow Sammy Davis Jr. to gamble in them, and thus got many casinos to repeal their policies regarding blacks. Segregation had effectively ended in Vegas by 1960, two years before the program is set. However, Sisko is likely correct that black people would still be treated differently than white people even in a desegregated Las Vegas and certainly much worse in most other corners of the country.
- Breather Episode: In a long and dark war arc. Also, an inversion, as the last lighthearted episode before a string of serious episodes.
- Briar Patching: Ezri tricks the substitute accountant into drinking the drugged martini by asking if, since he says he doesn't want it, she can have it instead. As expected, he drinks it just to spite her.
- Brief Accent Imitation: While waylaying the money counter, Bashir fakes an American accent.
- Butt-Monkey: O'Brien's part of the heist works a little too well: he ends up getting strip-searched for the chips he "stole" from Kasidy.Bashir: Where have you been?
O'Brien: I don't want to talk about it.
- Call-Back: When talking about their reasons for helping Vic, Nog mentions Vic helping him cope with losing his leg and Kira cites his role in getting her and Odo together.
- Character Shilling: Part of the purpose of the episode was to sell Vic to viewers who still didn't like the character.
- Continuity Nod: In the 24th century, racism - at least between humans - seems to be a thing of the past to the point that such a concept is completely foreign to most humans in the Star Trek universe. So why does Sisko bristle over going to the 1960s, even through a holodeck? Because as Benny in "Far Beyond the Stars," he lived in that time period, and he knows full well how deeply racism ran in humanity back then.
- Despite the Plan: Nothing goes as planned (the count room has a different accountant, someone spills the spiked drink, the safe has an auto-relock tumbler, etc.), but everyone is able to improvise enough to pull it off. They actually show us what the plan looks like when executed perfectly, too, and even mislead us a little into thinking it's the actual performance of the plan, with the characters narrating/explaining their parts.
- The Don: Carl Zeemo, who Frankie Eyes reports to. The caper involves ripping off Zeemo's "skim" of the casino's profits and making it look like Frankie's the thief.
- Don't Ask: O'Brien gets strip-searched off-screen. He does not want to talk about it.
- Evil Is Petty: Frankie dislikes Vic because he used to beat him at stickball
- Fanservice: A dolled-up Kira and Kasidy, as well as Ezri in a cocktail dress. For those who like the fellows, Sisko rocks a very sharp tuxedo.
- Fantastic Racism: Downplayed; Worf likes Vic's singing, and has nothing at all against the guy, but doesn't consider a hologram to be a person in any way.
- Fisher King: When Frankie takes over Vic's club, it turns from a tasteful jazz bar into a sleazy burlesque club. When Frankie is led off at the end, it reverts to Vic's.
- Gone Horribly Right: The "jack-in-the-box" was installed to keep Vic's program from getting boring; Felix didn't account for the crew getting attached to Vic and his world just as it was.
- Hammerspace: Justified when Vic asks how they plan on just walking away with a million dollars, Odo explains that he'll hide it inside himself.
- Heist Episode: The characters have to steal a million dollars in what's basically an homage to Ocean's 11.
- Holodeck Malfunction: This holodeck malfunction episode explains the problem as intentional: Felix designed this little unalterable adventure to prevent the program from getting stale, so the whole crew has to use their free time away from fighting a war to plan a heist in 1962 Las Vegas.
- Honey Trap: Kira's job is to seduce Frankie and keep him distracted while the heist takes place.
- Large Ham: Sisko enjoys the role of High Roller almost too much.
- Laxative Prank: Bashir gets rid of the lone remaining monkey counter by spiking his cocktail with ipecac, making him run off to puke.
- Leaning on the Fourth Wall:
- O'Brien points out the absurdity of the situation, even as he is fully committed to the plot:O'Brien: "Robbing casinos isn't part of any Starfleet job description I've ever read."
- Just after Frankie sees that the money is gone, there's a Smash Cut to the burlesque dancers outside, with one of them pantomiming Sean Connery Is About to Shoot You, highlighting what is about to happen to Frankie out back.
- The final performance of "The Best Is Yet to Come" was supposed to herald the following nine-episode final arc of the show. However, this episode was ultimately moved up in the airing order.
- O'Brien points out the absurdity of the situation, even as he is fully committed to the plot:
- Money to Throw Away: Sisko resorts to this at the end to ensure Nog and Odo escape, tossing his bankroll in the air and creating a frenzied scene. Bashir joins in with his poker winnings.
- Oh, Crap!:
- Nog, when he realizes that the safe is more complex than he expected.
- Frankie Eyes, when he opens the safe to find it empty.
- Planet of Steves: Cicci tells a story about how he once killed Little Paulie when he was supposed to pop Big Paulie."That's the problem with our business! Too many guys named Paulie!"
- Politically Correct History: Discussed. Sisko, who is African-American, is annoyed at the popularity of Vic's holosuite program, which gives a politically correct depiction of 1960s Las Vegas that leaves out the 1960s USA's racial segregation. Sisko points out that in the real 1960s, neither he nor his also-black girlfriend would have been allowed into the casino except as performers or menial staff members. She argues however that it's defensible as being how that era should have been in reality. It's somewhat averted, in that Vic is a pretty blatant expy of Frank Sinatra. Sinatra himself was way ahead of his time regarding racial issues, and in fact forced a few hotels to desegregate (his group would refuse to play at hotels that practiced racial segregation).
- Power Walk: The senior staff walks in their con outfits through the promenade. Lampshaded by Quark, who observes the Power Walk and tells Morn something big is obviously going down at Vic's.
- During the caper, Bashir orders a vodka martini, but stirred, not shaken.
- Frankie complains that there's no statue of Bugsy Seigel in Las Vegas. This is a reference to The Godfather Part II, in which Hyman Roth makes the same complaint about Moe Green, the No Celebrities Were Harmed version of Seigel.
- Slipping a Mickey: Bashir's role is to put ipecac in the accountant's nightly martini, forcing him to leave the count room.
- The Tease: In spite of being the Honey Trap, Kira never so much as lets Frankie kiss her. In fact, Frankie has an unusual tolerance for being strung along, likely because the program author Felix specifically decided to not force the players to prostitute themselves out to play the game.
- This Is Gonna Suck: After Frankie opens the safe only to show Zeemo that he has no money, he is "escorted" outside, a solemn look on his face as Zeemo's goons draw their guns.
- Title Drop: Cicci says "Badda-Bing, Badda-Bang" while recounting a story of how he popped off the wrong gangster.
- Unspoken Plan Guarantee: The plan is spelled out to the audience explicitly, complete with demonstration, so you know it's going to go sideways.
- We Used to Be Friends: Frankie and Vic apparently grew up together, and Vic jokes Frankie's ruining his life because Vic used to beat Frankie at stickball.
- What Measure Is a Non-Human?: Vic is considered to be a life form by the crew, and even though the crew isn't in any real danger (the danger is only to the holographic Vic who is part of the program), they still undertake a complex plan in the holodeck to save him. For his part, Vic is self-aware and knows he's a holographic character. Given that every part of this was a deliberate design choice, you really have to question the programmer's mental state.
- Xanatos Speed Chess: Unforeseen complications force the crew to improvise to keep the plan on track.
- You Have Failed Me: Frankie is disposed of by Zeemo's goons in the usual mafia fashion.
- Zip Me Up: Odo zips up Kira's dress.