Hate them all you want but Maggie, Hayden and Andy completely dominated their seasons by constantly staying on top of the pyramid. Will and Dan are a bit of an asterisk though. They repeatedly made themselves a target which should make them questionable winners, but had this ridiculous amount of charisma and/or savvy-ness to get themselves out of any situation while remaining COMPLETELY emotionally detached.
Mid Tier:
Jun/Boogie
Jun had this very rare talent of never being the one who called the shots but always setting herself in the best position every single time the dust settled. As for Boogie, I disagree with people saying he rode Will's coattails, he was just as active a player as Will. But yeah, he wasn't top dog either so he misses out on top tier
Low tier:
Lisa/Drew/Adam/Ian
Benefited from someone else doing all the work, all lesser of two evils.
Bottom tier:
Dick/Jordan/Rachel
Beating a dead horse, but yes all rigged winners. Even their most hardcore fans can't/won't defend their wins.