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While O'Brien wasn’t a officer, he is a decorated war veteran with multiple years of experience on the field, so that definitely makes him more qualified than, let’s say, Sisko, who as far as I can remember had exactly 0 experience on the military side of Starfleet before the Ds9 posting So if we assume the Obsidian Order is basically the Lizard KBG and Garak worked for them off-world, then yes, he is definitely the more experienced there, quickly followed by O'Brien. However, there’s also the whole Romulan tale, which if taken as true (and probably there are some truths in there), then Garak was definitely involved in political espionage and assassination in foreign territory. Finding, torturing and destroying any possible inner threat to the regime from within. A lot of hints (his relationship with Dukat being the main one) make me think that he did a lot of, er, inner surveillance. It depends on what Garak precisely did, and the sources are… not exactly transparent on that matter. I mean, it’s debatable? Let me rant a moment as someone who is currently mid season 5 for the first time ever.