I've been on a bit of a nostalgic DS9 kick lately (that's Star Trek: Deep Space Nine for the uninitiated.) My favorite character on the series is actually never listed as part of the main cast, despite being a major character for all seven seasons.
The basic premise of DS9 is that the Cardassians (whose empire is a totalitarian, fascistic society) have finally ended their occupation of the planet Bajor after sixty years, likely due to the influence of the Federation. Ben Sisko, a Commander in Starfleet, is given command of "Terok Nor," a Cardassian space station that had been used as a base of operations for the occupying forces, which Starfleet has renamed Deep Space Nine.
There's a lot of drama mined from the scars left by generations of military occupation and oppression, and also the desperate and morally ambiguous measures the Bajoran resistance took to fight off the occupation.
While the Cardassians transfer control of the station to the Federation (with a strong implication they'll take any opportunity they can to take it back,) there is one lone Cardassian civilian who is left behind - Elim Garak, a tailor who has a clothing store on DS9's Promenade - its sort of communal "main street."
Of course, it becomes obvious very early on that Garak is actually a veteran intelligence operative with the Obsidian Order, Cardassia's intelligence agency - or rather, he was. Garak is a fascinating character because, while it becomes clear that he wishes to help the Federation and preserve Bajoran freedom, he is also tied to his own people. Also, a life in the cloak-and-dagger business has made him both extremely wary of others and also very cynical about them. He also has a sort of "realpolitik" view of things that allows him to engage in actions that clash heavily with the ideals of Starfleet, even at one point assassinating a (relatively) innocent diplomat for a grander political purpose.
He's a great character, and it got me thinking: how would one make him in D&D?
A couple things are obvious: he's a Rogue, and he's got the Spy background. I might swap out a language for proficiency in tailoring tools - it is, after all, his cover. I'd also give him the Mastermind subclass, as that's the sort of deft manipulation that he would employ (as always, I think College of Whispers bards work quite well for spies and assassins, so he could multiclass into that as a possibility.)
Now, what about race?
I've often contended that many Star Trek species can be easily translated into fantasy races. Humans are humans, obviously. Klingons are Orcs, with their obsession with warfare and battlefield honor (particularly their failure to live up to those ideals and tendency to devolve into bloodlust.)
(The Borg are also basically sci-fi zombies.)
Now, Vulcans and Romulans present a quandry.
In generic fantasy, I'd say they make for really obvious High Elves and Dark Elves. Indeed, the Drows' ruthless and cutthroat society fits quite well with the Romulans. They even have the requisite pointy ears. And Vulcans are, similarly, "good guys" but also infuriatingly smug about that status, usually looking down on humans even as humans catch up to them in just a handful of generations.
The thing is, we also have the Gith. The Gith are, I would bet, directly inspired by the Vulcans and Romulans. Not only do they have psionic abilities (Mind Meld, anyone?) but their cultures are even divided in similar ways.
The Githzerai, with their focus on a sort of monastic practice of balance, feel directly inspired by the Vulcan ideals of Logic. Meanwhile, the Githyanki, hiding away on the Astral Plane with a serious "kill first, ask questions only if the prisoners survived" attitude feel quite akin to the Romulans.
The Cardassians are, frankly, kind of B-tier Star Trek aliens - not in terms of quality, but in terms of recognizability. Someone who has never seen an episode has probably heard of Klingons and Vulcans, but it's very likely they think Cardassians are a bunch of reality-show stars.
Now, if we say Drow are Romulans, that frees of Githyanki to be Cardassians.
But I think I might instead go with Hobgoblins.
Hobgoblins are kind of fascinating to me as a race, given that the other two major goblinoids, the standard goblin and the bugbear, are both sort of dumb and chaotic. Hobgoblins, however, have that totalitarian vibe to them (the Hobgoblin Iron Shadow is a stat block for a monastic secret police order in their society.) They place a high value on their status within their society (see the "Saving Face" racial ability), and are quite intelligent.
This all fits pretty well with Cardassians.
So that's what I'd go with: a Hobgoblin Mastermind Rogue with a Spy background customized to allow proficiency in tailoring tools (or maybe train for it with downtime.)
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