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Tuvok was on board the Enterprise B!!!

Not to mention the Dominion's total infiltration of both the Andorian Empire and the Ferengi Alliance decades before the war with Agent Weyoun.
 
What about that time Kirk's son and Khan's chief henchmen learned the secret of electric eels and became druggies on some dumpy Next Gen planet?
 
Or how about Dr. Pulaski on TNG all of a sudden encountering Dr. Ann Mulhall and Miranda Jones in a random corridor. Will the fabric of space-time be torn apart?
 
Quark, who in an earlier life was Colonel Walter E. Kurtz (Apocalypse Now), lived inside the walls of Sunnydale High School (Buffy the Vampire Slayer). His evil twin was the school's principal, until he was eaten by the town's mayor during graduation ceremonies.
 
Or how about Dr. Pulaski on TNG all of a sudden encountering Dr. Ann Mulhall and Miranda Jones in a random corridor. Will the fabric of space-time be torn apart?

Cue a three-way reinactment of the Stewie/Hitler scene in Family Guy's "Road To Germany"
 
Quark, who in an earlier life was Colonel Walter E. Kurtz (Apocalypse Now), lived inside the walls of Sunnydale High School (Buffy the Vampire Slayer). His evil twin was the school's principal, until he was eaten by the town's mayor during graduation ceremonies.

He was also 90% of the Ferengi the crew met during TNG.

Armin Shimerman and David R. George III's novel "The 34th Rule" had the DS9 crew meet every single one of them during Quark's absence. Bizarre.
 
There is a rumor that Zefram Cochrane has spent time touring the Galaxy under several aliases, including: Nayrok, Jaglom Shrek and Hanok.
 
After getting his mind wiped, Kurn travelled to the Delta Quadrant and infiltrated the Hirogen. He also looks strikingly like adult Jake Sisko.
 
That because Kurn was slipping Jennifer Sisko the juice

Jake is actually a Human-Klingon hybrid.
 
Roga Danar from TNGs 'The Hunted' obviously got rehabilitated by his planet's government, joined Starfleet, and worked his way through the ranks to become Voyager's original Chief Medical Officer.So his behaviour towards Tom Paris in 'Caretaker' is a bit hypocritical. He of all people should know people can change! :)
 
Not forgetting the warp specialist Leah Brahms. She was so afraid of Geordi's crazy stalking that she changed her name, got tired of designing engines and decided to fly them instead. Unfortunately it ended rather messily when she became embroiled in an ateempted Starfleet coup d'état.
 
And Saavik in TSFS was actually called T'Paal, who later posed as a Romulan mercenary named Tallera. Nobody seemed to notice how different Saavik looked in TSFS from TWOK
 
And who can forget Neelix, who was really a banished Ferengi and got the chance to air out his hidden lobes while helping Voyager get rid of a few lost brethren of his.
 
And there was Leonardo da Vinci, who became Mr Flint and later (as a hologram) a plaything of Captain Janeway.
 
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