Dukat

In the years before the United Federation of Planets intervened in Bajoran affairs, Dukat was the head of the Cardassian ore processing facility Terok Nor and the boss of the Bajoran Occupation. Many Bajorans rebelled against Dukat and the Cardassians to end their occupation.

When the Cardassians finally left Bajor, the Federation moved into Terok Nor, now Deep Space Nine, and discovered the Bajoran wormhole. This made Dukat very unpopular with Cardassian government, and as such made Dukat very annoyed at one Benjamin Sisko, vowing one day to get back Terok Nor.

During the course of the series, Dukat and the Cardassian Union joined with the Dominion, found and lost his half Bajoran/half Cardassian daughter Ziyal, and became the Pah-wraith[?]'s emissary.

In the series finale, Sisko and Dukat fought each other to see who was the better man. In the course of the fight, Dukat became imprisioned forever with the Pah-wraiths.