Dominion
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The Dominion is a vast alliance of hundreds of species in the Gamma Quadrant ruled by the Founders. The Federation first came in contact with the Dominion a little after Starfleet discovered the Bajoran Wormhole. The Dominion allied themselves with the Cardassian Union in the 2370s and fought the Federation, Klingons, and Romulans in the Dominion War, ultimately surrendering and withdrawing back into the Gamma Quadrant in 2375.