There's not a huge amount of interesting trivia about the episode. Apparently it took quite some time to break the story, with the original concept being Jake uncovering dirt on First Minister Shakaar and Sisko tried to make him kill the story; and then he'd uncover a conspiracy that his father and Garak were involved in, and eventually it became Sisko baring his soul about the conspiracy.
And, uh, the episode's title is a reference to the Joker's line from Tim Burton's Batman.
So this is another favourite Trek episode overall for me. I wouldn't recommend it the same way I would Far Beyond the Stars, but only because it needs the weight of 6 years of time with Sisko to really work. That's because of the Captains to that point, Sisko is the most human, largely because he's the most changed by his experiences in the show's lifespan.
In his time as commander of Deep Space Nine, Sisko has moved from being reluctant about his posting on Bajor and his role as Emmisary to loving his adoptive homeworld and accepting his position as a religious icon. He's seen his son grow into a young man, he's been a father figure to Nog, a mentor to Worf and Kira, but throughout all that, he's also been a man willing to go to extreme measures to defend the things he loves.
It's important to remember that last part, because this isn't the first time that Sisko has essentially committed a war crime. He rendered Maquis planets uninhabitable over the objections of his crew the prior year, so we know what he's capable of. And while that action was quite dark, it was still sorta Trekky (as opposed to Trekkie), because he did it in such a way that Cardassians could still live there, so they just swapped Maquis and Cardassian populations between some contested worlds, what happens here isn't as neat and easy.
I tend to agree with @SimonJones rather than @Mike on how much Starfleet knew about the plan. Given that Sisko was somewhat in the dark about Garak's intentions beyond "we'll fake a recording", I don't see how Starfleet could approve of any of the really awful stuff which followed, and at the higher level the plan isn't much worse than routine espionage.
So the question becomes "did Sisko tell Starfleet what happened after he knew all the facts?" And given his rant at the start of the episode I think the answer to that is no. At best they know about Sisko ordering Bashir to provide the biomemetic gel to buy the data rod, and that's because the order was in writing and Bashir logged a formal complaint.
But in many ways the other acts Sisko takes part in are worse. He has to bribe Quark (thus personally proving that Federation morality is not absolute), and he has to stand by and let Garak literally get away with murder to maintain this new advantage in the war.
The second-last line of the episode is the most telling - I can live with it. I can live with it. Sisko knows that his personal surrender to immorality is less important than the survival of the Alpha Quadrant's extant nations. The cost of the Romulan entry into the war is worth the life of one Romulan senator, one criminal... and the self-respect of one Starfleet officer.
The needs of the many outweigh the needs of the few... Or the one.