Veteran: 14th Challenge
the ultimate "sly fox," wes enters this season with a truly outsized -- and well-earned -- reputation for his cunning political game. in particular, the two-time champ is known for two things: deal-making and befriending rookies. this kansas city, mo, entrepreneur is also not one to shy away from big moves and seizing command of the game. for all of his political masterminding, wes hasn't taken home a "challenge" win in many seasons, and he may need to rethink his strategy this time around if he wants to bring home the prize to his wife amanda and their dog bootstrap. unfortunately, with a reputation like his, winning may be hard to do, as he is almost certainly guaranteed to come in with a target on his back.