Star Trek Characters That Need To Meet Each Other (Somehow)

It has become a bit of an internet meme to decry the fact that Andrew Robinson’s Garak and William Sadler’s Sloane never shared the screen during Deep Space Nine’s run. Sloane represented all that was conspiratorial and dark about the Federation, wrapped in his black leathers - an obvious visual metaphor. Garak, on the other hand, wore bright colours, a bright smile, and was one of the deadliest characters ever introduced to the canon. 

Garak’s relationship with Section 31 may also have been tangential - it was Bashir was courted by them, so one could argue he never came within their purview. However, it would be naive to assume they didn’t have a dossier on him - nor he on them. For Garak and Sloane to meet, it might spell catastrophic things for the Alpha Quadrant, but it would certainly have been a meeting for the ages. 

Comparing interrogation notes, sharing anecdotes about Julian, and even tossing back a bit of Kanar while the Quadrant burned wouldn’t seem out of the ordinary there. Expanded canon has established Bashir as working for Section 31 (who doesn’t, these days?) so having Garak as a personal acquaintance of two separate heads of the organisation seems simple. 

Plain, and simple.