4. Art Jimmerson
At UFC 1, Art Jimmerson was the man who famously wore one boxing glove into the cage with Royce Gracie.
Now, this is going to sound ridiculous but when the UFC first hit this scene many people thought kick-boxers would dominate. Even though it was being organized in part by the Gracie family, few fighters in the United States gave the grapplers much chance.
Jimmerson must have felt that keeping his jabbing hand protected with the glove was a smart idea. Unfortunately for him, Gracie was never going to give him much of an opportunity on his feet so all the boxing glove did was take away the use of his hand on the ground.
In a happy ending to this story, Jimmerson now works as a boxing coach in the UFC Gym in Las Vegas.