Overall, I look at Kane's career and his dominant performances in Rumbles and it always surprises me that he never won one. But as
@RollSonnenRoll pointed out, his best run was at a time where other guys were going over. 2001 was his huge year, and nobody but Austin was winning that. The next year was Trips big come back and after that Kane wasn't quite that monster anymore. He could have won in 99, but they had the Vince angle they went with instead. I can't remember what he was doing in 2000. Since they botched the main event of WM anyway, he could have won there instead of Rocky and they could have made it a stupid 5-way with Vince's other son, Hornswaggle, in Kane's corner.
I voted Bryan because there was a specific Rumble (2014) that he should have won, imo. It worked out fine in the end, but failing to book him to go over in that Rumble really made me question if the creative team even watched the shows.
I probably should have included Warrior. He would have been a solid win in the early years - one of the ones Hogan won, before the WM tie-in.