: Especially since he believed, and with good reason, that the Rommies would be forced to fight the Dominion eventually, and would indeed be better off in the long run if they joined the UFP's coalition. It's technically a dillema, yes, but it's also a pretty easy one. As I said in a previous thread on this, I gotta agree with Michelle Erica Green on this one
I must say that I think the flashback-via-diary structure for this episode was a mistake, because I had a really hard time not laughing at Avery Brooks' earnest, emotional monologues in Sisko's personal logs.
.... I have to believe Sisko was upset because Garak was a cleverer saboteur than he was himself, not because he played nasty. If he was really feeling guilty about the dead enemy agent and the man the Klingons were going to execute anyway, his skin isn't nearly tough enough for him to be a captain during wartime. Garak wasn't even amoral in this episode as he so often is - his decisions were quite effective as he plotted to get the maximum Federation protection with the fewest lives lost. I thought the twist at the end was going to be that he was up to something far more personal and nefarious, not that he was trying to shoulder the responsibility for something he thought Sisko might not want to do himself.