In theory, Star Trek is an optimistic look into the future. However, that's just the lens from a hopeful Starfleet officer's bridge. The universe around them, in reality, can be a much more twisted and complex place. For example, many powerful governments (including Starfleet itself) have secret organizations doing all they can to manipulate and undermine each other.
Spies have been an important part of the Star Trek universe since its conception, showing the dark underbelly of the pacifist utopia. Only some of those spies are truly among the best, though, causing as much trouble and espionage as they can. Here are the 10 best spies in Star Trek, ranked.
Seska
Okay, yes, Seska's cover was totally blown on Voyager. They discovered her Cardassian heritage and she went totally off the rails. However, before Voyager, Seksa was a very successful spy. She tricked the Maquis into trusting her so deeply that they befriended her, loved her. She was able to funnel Maquis secrets to the Cardassians with ease, because they fully believed her.
Instead, though, she was using them for information. Maybe her feelings for Chakotay were somewhat true, but her friendships, her alliances? She played them all. That's a disturbingly good spy who only got caught with her exit plan on the other side of the quadrant.
Arissa
Arissa was a spy so deep undercover that she had her own memory erased. Instead, she had a different life implanted in her brain. That made her think she was that person, naturally adopting their associated feelings, tragedies, and passions. Unfortunately, her fellow spies did it a bit too well. Arissa got away from them and started to hunt their target on her own, leading her to DS9.
With luck, though, they caught up to her in time for her to catch her man with Odo and then give her back her real face and life. Sure, the memories had some influence, but even her fake persona was pretty great at tracking people down and stopping dangerous criminals.
Eris
When Sisko and Quark first encountered Eris, they thought she was a fellow prisoner of the Jem'Hadar. She supposedly was on the run from them but they caught her, and wanted to work with them to escape.
Lo and behold, they find out she's actually a Vorta, a people dominated by The Founders to act as their spies and intermediaries. However, they didn't know that until Eris revealed herself. So, she did a pretty great job spying on them and finding out what she could about these humans from the other side of the wormhole.
Michael Eddington
Throughout DS9, the Maquis are a problem that the station doesn't know how to deal with. After all, in the Cardassian Treaty, the Federation gave back planets and space that were already settled for years by human colonists. While the Cardassians were happy with this deal, the settlers were not. They fought back against Cardassian occupation and became a movement of their own.
Much to Sisko and the rest of DS9's surprise, their security officer turned out to be a spy for the Maquis: Michael Eddington. He became a thorn in his side, a white whale for Sisko. After all, he stole Federation tech and knowledge right from under Sisko's nose.
Commodore Oh
Embedded in the Federation as a Vulcan Admiral, Commodore Oh was secretly a half-Romulan operative of the Zhat Vash. She hid herself in Starfleet to get as much information as she could and to orchestrate the Mars attack, to make The Federation mistrust and ban synthetics.
Influencing policy and Federation decisions for decades, Oh was a frighteningly effective spy. Luckily, Picard and his crew exposed her organization's machinations and exposed the truth behind her actions. Then, they could treat synths like the people they were.
Luther Sloan
The leader of Section 31 during the Dominion War, Luther Sloan did a lot of spying himself, but also ran some of the most effective espionage operations in Starfleet history. The fact he used a helplessly moral man to put his own Romulan agent in power was terrifyingly ingenious.
Though the war made him a little bolder with his actions, getting him noticed by DS9 for one of the first time in years, that was probably all calculated, too. He was really good at being insidious and clever, making him an amazing spymaster.
Selok
One of the most effective Romulan spies of all time was Selok, who infiltrated Vulcan under the name Ambassador T'Pel. She became a revered peacemaker, one of Vulcan's most revered. She collected as many secrets as she could for decades before being called back to Romulus.
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They planned to fake her passing, make her disappearance a tragedy. However, some engineering caught her out on her lie. The fact Selok almost got away with the decades-long con, though? That's one impressive spy. She had to pretend to subscribe to Vulcan ways for so long, which must have been grueling for a non-Vulcan.
Enabran Tain
The father of the Obsidian Order and Elim Garak, Enabran Tain was a spy who changed the course of his people's history. During the war between The Federation and Cardassia, the Obsidian Order was vital in extracting information, finding secrets, and coercing the tides of war.
While Enabran was a horrible father, he was a mastermind of making people putty in his hands. That came in handy in his work, and eventually helped him disappear later in life. The only person who found him out was his own son, Garak. That's one slippery dude.
The Founders
As powerful shapeshifters, the Founders have deception built in their DNA. That wasn't how they used to be, they used to be a friendly, curious people. However, mistreatment caused them to hone their ability to lie and manipulate those around them. When they started their assault against The Federation, they quickly infiltrated and masked themselves as Starfleet members. They were almost impossible to track.
That is, except for some very particular blood tests. Either way, they took the places of some of the most powerful people in the galaxy, without anyone noticing for months at a time. That's impressive and horrific all at once.
Elim Garak
Even though Elim Garak was not a practicing spy by the time DS9 fans met him, it's clear he was one of the best. He's capable of coercive conversations, infiltration, espionage, and even still had countless contacts from his spy days.
No matter how chill and sly Garak tries to play it, he's the legacy of an Obsidian Order legend, he helped Sisko bring the Romulans to the Federation's side of The Dominion War, and he was the only one capable of breaking the prisoners from The Dominion jail. Garak can be a really mysterious man sometimes, and everyone knew his "simple tailor" bit was an understatement. But Garak deserves all the credit for being the most wily spy in the Star Trek universe.