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Characters from different "Star Trek" series who should meet

Pitted against each other? I think, compared to Quark, Neelix is a good-willing, but sorry amateur. Quark would have him for lunch. It might work if they were on the same team, though.

Neelix was apparently intended to be Voyager's version of Quark at first.
 
Just imagine Lorca's reaction to the moment Picard starts giving one of his self-righteous holier-than-thou speeches.
Picard: "Captain Lorca, I should not need to remind you that as Starfleet Captains we have an obligation to uphold the values of the Federation. It is our sworn oath that no matter how dire the circumstances, how desperate the situation we will not forget what it means to where this uniform or indeed our very humanity. To do otherwise is to accept we have already lost."
Lorca: "I don't give a damn."
 
Lorca and Alex Marcus. They'd become instant BFFs and turn the Federation into something utterly monstrous.

Over in the Kelvinverse, Spock Prime, Guinan and Data's severed head need to team up and fight crime.
 
It might be fascinating to see a Romulan ship and crew, during their travels, happen upon the planet in "Bread and Circuses". Romulans meet Romans.

Or, Odo encountering the salt vampire. A shape shifting contest. Who can shape shift better?
 
How about the tar monster from "Skin of Evil" meeting the Crystalline Entity?

Of course, the best would be Khan meeting all the would-be Khans from the Next Gen era (Dr. Tolian Soran, Borg Queen, Ru'afo and Shinzon) and seeing him whooping their asses.
 
Pitted against each other? I think, compared to Quark, Neelix is a good-willing, but sorry amateur. Quark would have him for lunch. It might work if they were on the same team, though.

Quark would try to get him to cook DQ dishes to sell as exotic delicacies for extreme markups, and take advantage of his lack of economic knowledge to severely underpay him.

How about Nog and Kim.

"You went from first year cadet to lieutenant in HOW many years?!"
 
^Nog: <knocking on his leg prothesis pretending nonchalanche> .'...and all I had to do for it was fight in the war and loose my leg'.
< Kim gets green in his face> : 'I'd rather stay an ensign then, thank you very much'.
 
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