While Judas only had to endure the shame of what God designed him to do for a human lifespan, and a prematurely short one at that, Lucifer was immortal, and thus had to be slandered and hated for eternity by the creation that he tried to free. Lucifer was the victim of a very bad case of history being written by the victors.
In Christian teaching, we find that Lucifer, or the devil, got exactly what he wanted, which was to be his own master. While Christians are taught that he will ultimately lose, he was able to get what he wanted, and likely has no remorse for it. Conversely, Judas, who betrayed Jesus, was so overcome and overwrought with what he had done, that he committed suicide. Because Judas was able to sense that he had done wrong and actually have an emotional response, he definitely is the one who would have felt that he had gotten the worst end of the bargain in the grand sceme of things.