Star Trek does Ocean's Eleven two years before the George Clooney film (which would mean more if the episode didn't happen 39 years after the Rat Pack original) in this ensemble caper episode that gives the DS9 cast another chance to cut loose and have some fun.
With a flimsy premise that's another variation of the old malfunctioning holodeck idea, even the writers know the audience is going to have to suspend its belief more than usual. (They do help themselves by establishing that only a holographic character is at risk, which is easier to swallow than a real person... though the episode's promotional spot is artfully edited to make it sound like everyone is in danger). But like "Our Man, Bashir" and "Take Me Out to the Holosuite", the plot itself is secondary; what this one is really about is a chance to get the cast into some new clothes and to do something left of center for the franchise.
Veteran character actor Robert Miano stars as Frankie Eyes, the episode's heavy, which would seem like an opportunity for hamminess, though Miano (apparently taking this a little too seriously) plays it straight. With Mike Starr as his right hand man Cicci, and 89 year old Marc Lawrence as his boss, Mr. Zeemo, however, there's plenty of scene stealing performances. (In fact, the replacement accountant, played by a "Bobby Reilly", is pretty good in his own right. Maybe they should turn him into a Klingon leader or something).
Perhaps the most notable character in the whole deal, however, is Sisko. Used initially as an audience surrogate for those who dislike Vic Fontaine, he's ultimately won over and steals the show at the end with a special coda stuck in by the writers to show off his talents and send a message to the fans about the last few episodes of the series.
It's all tied together by Jay Chattaway's score, a throwback to the 60s with classics like "Night Train" thrown in that perfectly matches the old style cinematography.
All in all, it's not something DS9 would want to do every week (especially since it's one of the most expensive episodes of the season), but for a breather before the big war stuff that's upcoming, it's a lot of fun.