Johnny Bananas — Rivals 2/The Island
This was a tough one for me. It’s easy to point to a season like Duel 1 where he lost on the first episode, but that was regular rookie troubles. It’s especially weird as these are two Challenges that he did well in on paper. His first win was the Island, but the way he treated women and carried himself was just atrocious (even he’s stated that he can’t watch the Island). Rivals 2 is also up there for him as he kept gassing out on all endurance based challenges, and he and Frank got smoked by CT & Wes in the final. This season was a wake-up call for him and he went on Free Agents in much better shape.
Darrell Taylor — Fresh Meat 2
After winning his fourth straight Challenge on Fresh Meat 1, Darrell came back to win his 5th on the Ruins. He left the Ruins dramatically by getting into a fight with Brad where he demolished his face and left the season disappointed in himself. He returned the following season to make up for his embarrassing exit, but was quickly blindsided by Wes, who got the whole house to throw him into the first exile(including his arch-nemesis Kenny). His inability to do a puzzle got him and Cara sent home packing on the first episode, and left us with a bad taste in our mouth until he came back on Invasion.
Evelyn Smith — The Ruins
As much as I respected Evelyn turning on the Champions team for throwing her in against KellyAnne, quitting is kind of weak. I would have much rather watched throw missions in order to put her teammates in danger and lose them money. It is just a sad season, as this easily could have been another win for Evelyn, but she chose to quit instead.
Wes Bergmann — Battle of the Seasons(2012)
Despite being one of the greatest competitors ever, Wes had more than one season eligible for this(Fresh Meat 2 and Exes 1). On Battle of the Seasons, Wes went into the game with the weakest team in the house, even though he was the best player. He pulled the worst elimination to face Big Easy in, and left on the first episode. All of this was pure bad luck, so why is this the worst season for Wes? It was a culmination of his seasons prior, Wes had gone from top tier competitor to lasting only 3 episodes combined for 2 seasons of work. This forced Wes to play the game from a different angle from there on, he could no longer try to be a physical alpha, he’d have to focus mostly on the political.
Cara Maria Sorbello — Exes 1
Her first two seasons she gets the pass for being a rookie who is new to the Challenge. On Exes 1, she was at her worst playing with Abram as her teammates. She was almost catatonic during certain daily challenges, often relying way too much on Abram for help when she was physically capable. After watching her become a strong competitor and finishing second on Rivals 1 with Laurel, she just had a plain bad showing.
Kenny Santucci — The Duel/Rivals 1
Rivals 1 is only on here for the sheer fact that Kenny kept DQ’ing his partnership and getting them into eliminations where Wes consistently clutched it for them. However, he killed it in the final.
What is funny about Kenny, was that it wasn’t until about Gauntlet 3 where people had the consensus feeling that he was a good competitor. On the Duel 1, Kenny wasn’t seen as a good competitor, he was just the dumb pretty boy. He got called out by Nehemiah on the 3rd Duel, and gotten taken out, the only time he has ever been eliminated on the Challenge. My favorite acknowledgement of Kenny not being seen as that good was when he and Ace were up for elimination and trying to get the life-shield in order to save themselves, Abram says: “have you seen these guys in the Challenges? They’re not getting the life-shields, they suck(laughs).”
Sarah Rice — Fresh Meat 2
After an incredible rookie season on the Ruins, Sarah came back for Fresh Meat 2 where she was way too cocky and picked a partner based on appearance(Vinny), rather than performance. They were the second team to go home, and unfortunately she did not come back for the following Challenge humbled either.
Evan Starkman — Rivals 1
Like CT said, Evan came back pregnant. He gained a lot of weight, and was nowhere near the guy that dominated the game on his seasons prior. Sadly, this was his last appearance on the Challenge.
Rachel Robinson — Exes 1
Maybe it was because she was saddled with Aneesa as a partner(would make me sad), but Rachel did not play with her heart in the game. After dominating the Duel 2, she came back for another Challenge only to not be the physical beast that she once was. Praying that Rachel comes back for one more.
Alton Williams — Battle of the Seasons(2012)
This is the warning story for legends who try to return the Challenge and try to dominate the same way they did in the past after an extended difference between Challenge appearances. Alton’s performance on the Gauntlet 2 is to this day legendary. He came back for Battle of the Seasons and just kept getting gassed. His endurance was not there, he could not keep up with the party lifestyle, and he basically quit on Nany in an elimination they should have won.
Coral Smith — Gauntlet 3
Veronica Portill0 — The Ruins
Syrus Yarbough — The Ruins
Timmy Beggy — Inferno 3
Chris Tamburello — Inferno 3/Duel 2