The reason why Wes is not on this list and KellyAnne is, is due to the fact Wes enjoys being the underdog and loves knowing he has everyone pressed. KellyAnne knew Wes being there would anger a ton of people, but she did not quite understand that going in that her boyfriend would get kind of bullied in a Challenge house. Wes was a social pariah due to the way he carried himself and his actions on the season. However, he talked about his experience on the Ruins, where people set up a treadmill next to where he slept and took turns running to fuck him up for his elimination. Always playing pranks on him, and so on. Wes sometimes exacerbated and instigated these situations, but it was KellyAnne who was by his side who had to take the brunt of it.

Even worse, she had to deal with the Champs throwing in their best player and KellyAnne’s best friend in Evelyn into elimination to face either. So either she was going home, or her best friend was. KellyAnne had to deal with losing Evelyn, losing Wes, dealing with the misogyny of the males on her team, losing the strongest male on her side due to violence, having to be on the same team with creeps like Dunbar and Adam King, and then still coming up short. Considering KellyAnne’s first two seasons were the Island and the Ruins, it makes sense she didn’t come back for almost ten seasons.

6 Joss Mooney — War of the Worlds 2

Joss was in the majority alliance of War of the Worlds 2 where the players skated through the game and never saw an elimination as they controlled the numbers on both sides. Despite actively working towards his alliance’s needs, Joss reaped little of the benefits. When Kyle went into elimination, Joss was the first person to vote for Kyle, actively putting a wedge between the friendship they had since Vendettas. Why couldn’t CT or Rogan be the first ones to budge? Kayleigh made him the second vote to put Georgia into elimination, forcing him to be the bad guy. Why couldn’t she have made Dee the second vote? He had to be the one to face Bear in elimination, having no warning prior. Joss did everything he could to protect Rogan, Kayleigh, and Dee, and yet he had to face elimination despite being the best player among them. In the end, he got purged because the girl who controlled him could not swim.

Even after he got eliminated, Rogan pinned the move to put Dee in elimination on Joss. Joss was a follower not keen enough to lead, and he received all the punishments of a leader.

5 Derrick Henry — Dirty 30

It is one thing to get cheated on while your partner is filming a season of the Challenge. It is another to get cheated on by your partner while shooting the same season you were on. Derrick was an early elimination on Dirty 30. He got eliminated during the first real elimination and then lost the first redemption in the game. Tori made it to the final, where she finished in third place. While making it to the final, she became very close to Jordan Wiseley, eventually hooking up, and then starting a relationship off the show.

Derrick and Tori had a real-life relationship before the show aired and were on the show making a pact to have a baby if they both won. Jordan and Tori were meant to be, it is just the fact that if you rewatch those first couple episodes of Dirty 30, Tori and Derrick are all over each other, and by the end of the season, Jordan and Tori are a power couple. IT IS WILD.

4 Diem Brown — Duel 2

Diem had a rough run on multiple seasons of the show. Her losses always happen in the worst ways. The reason I put the Duel 2 over other seasons is mostly due to the CT/Adam fight, also known as when CT attempted to murder Adam. Diem and CT’s relationship had been over for a decent amount of time at this point, yet the two were always linked as we would go on to see for years to come. It was a rough night for Diem. She learned that CT had hooked up with Shauvon during their first hours at the house, and then she watched the man she had once loved go ballistic.

She would pull through and perform adequately through the game. Diem eliminated Jenn Grijalva, which does not sound impressive on paper, but Jenn had a 4–1 elimination record at the time (5–2 for her career). Unfortunately, she came up short, losing the final elimination of the season to Brittini. Diem lost the last elimination of three different seasons and the second to last elimination of another. It’s utterly heartbreaking how she would lose.

3 Devin Walker — Final Reckoning