Dukat and Weyoun and Kai Winn are all certainly infinitely more developed characters and better villains than any of Trek's other villains.
It's really a toss up between those three. They are all fascinating characters, and played immaculately by master actors. Isn't really any objective way to claim one of those three is better than the other, since all of them are perfect. All three of them are tied for Trek's best bad guy IMO.
I loved Weyoun. Firstly, those eyes are beautifully sinister. Bright, burning blue. But beyond that, he had that sense of humor and personality that just stuck around. Maybe not the most threatening bad guy, but he was a lot of fun to watch.
I felt Kai Winn was always bad. Like, to the point where it was just kinda ridiculous. Sometimes I wanted to be like, "Kai, you're doing something stupid again. Do you know what are you doing? Really? That? Oh, well, fine."
And Dukat? I liked Dukat. I think Dukat was evil in the people could almost begin to see how he functions. He had his daughter, and his family, and his pride and his job. Anyone can almost relate to that, and I think that's part of what makes him so ominous.
I think that he'll do well, but I think Khan will always go down in history as the best.
Will he be remembered as Treks best bad guy?
In terms of development, yes. However, he wasn't the most insidious evil character on Trek. He was motivated by greed and a lust for power, above everything else. Weyoun was programmed to be the way he was, and thus escapes some of the blame. He is what he is.
Sloan, on the other hand, did evil things not for personal gain or for his own fulfillment, but because he was a fanatic. To quote Mal from Firefly, "There's nothing worse than a madman who thinks he's right with God."
I'm in the process of watching Seasons 6 and 7. I'm currently on the Cardassian / Dominion occupation of Deep Space Nine.
I have mixed feelings about Dukat's character as a "bad guy." Sure he is an enemy of the Federation, but at the same time I don't consider him a true villian for some reason. He's not as evil as Weyoun and the Dominion in my opinion.
When I take a look at his tactical decision to "sell Cardassia to the Dominion," it appears to the be the best thing for Cardassia. They were a severely weakened Union, under constant pressure from Bajor, the Klingons, and the Maquis. Their alliance with the Dominion immediately thrusted Cardassia into its best state of power ever, and they finally could resist the pressures and forge an offensive. The also had the solid plan to rid themselves of the Dominion after the Alpha Quadrant was weakened enough. As evil as this plan sounds, it was tactically a great decision for Gul Dukat. When I watch the first war arc of Season 6, I see the Cardassian Union thriving like never before, and a confident Dukat actually keeping the Cardassian side of the alliance firm. He didn't let Weyoun walk all over him like Damar does.
Then when I look at his relationship with Sisko, he held such a great respect for Ben despite them being on opposite sides. It's more of a "no hard feelings" situation. Dukat recognizes power and is more concerned with the state of Cardassia and his position of power rather than the destruction of humanity. The Dominion was obsessed with destroying Earth's population and all the "solids," not Dukat.
Then I look at the situation with his daughter. She was the most important thing that mattered to him. He gave up everything for her - twice.
So when I look at Dukat, I see a man who is endlessly caught in an internal struggle between political power, his personal reputation, and being a good father. I don't see the vengeful villain that people portray him as.
I don't know, becoming the Anti-Emissary and nearly releasing a horde of evil Gods into our Universe is far more impressive than anything Khan or Chang did.
Dukat was definitely more developed but I think in terms of notoriety Khan beats him hands down. People who aren't necessarily Trek fans are more likely to know Khan, if only through "that" moment when he strands Kirk on what would be the genesis planet.
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