CATS (the winless character who's lost the most matches)
Chester (the weakest character we've ever seen)
Tanner (he'll never die as a benchmark for futility)
Gordon Freeman (GFNW is once again alive and well)
Cecil Harvey (the modern equivalent of GFNW because he keeps getting snakebitten in close matches, some of which he never should have lost to begin with)
Tidus (the biggest choker of these contests)
Draven (the ultimate hero to zero story)
Jay Solano (the character who's such a loser that he circled back to become the ultimate winner)
The only problem is deciding who the last character should be, because no one else particularly jumps out at me as deserving of such a lofty designation.
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"I believe in a universe that doesn't care, and people who do." You won the CBX Guru Contest, Advokaiser! Bully for you!