Okay thinking about that one deleted scene from The Wire script where Sisko mentions he and Curzon worked at the Federation Embassy on Romulus and his Romulan friend was arrested by the Tal Shiar (calculations w Sisko’s age put this around 2360), what if they were there at the same time as Garak? Like considering Romulans are pretty xenophobic, the Embassies are probably clustered together to keep the aliens in a single area and so if they were in the same city, there’s a good chance they would cross paths with each other at one time or another.