The start of the All Stars season might be deja vu. Ace left the first week and Trishelle the second. This might remind viewers of The Inferno in 2004.
They’re not the only ones who have left multiple seasons first. The Challenge has a long history, and people have found themselves in shitty situations multiple times.
To qualify for this list, a person must have been the first person to legitimately leave on multiple seasons. Disqualifications and quitting will not qualify someone. If you were part of a Purge, that counts because it could have been avoided. If the season has gendered eliminations, a player needs to lose as early as they realistically could have. So, Trishelle went home first on The Inferno even though she technically competed on four missions. However, don’t expect to see Bananas on this list. He might have been the first Veteran to leave The Gauntlet 3, but his team avoiding elimination #1 because they won.
Basically, you came in dead last if you performed as poorly as the format allows.
Honorable Mentions
Jon Brennan (Battle of the Seasons, The Inferno 2)- Jon lost in the first Inferno on Inferno 2, but he was voted out on Battle of the Seasons. That departure wasn’t based on merit, as the Miami and London team performed worse than him.
Veronica Portillo (Battle of the Seasons, Champ vs. Pros)- Similar to Jon, Veronica’s departure on Battle of the Seasons wasn’t based on merit. In fact, the Semester at Sea team was the fourth placing Road Rules team out of the eight Road Rules team. Her loss on Champs vs. Pros was and earned loss.
Ace Amerson (The Inferno & All Stars)

Ace has a history of leaving early. On his first season, The Inferno, he left first. On his second season, Battle of the Sexes 2, he left second. Eventually he would improve, but All Stars reverted him back to his bad luck. He was the first person to go home.
Trishelle Cannatella (The Inferno & All Stars)

Unlike Ace, Trishelle did pretty well on her first season. The second time around she was mentally checked out of the game and was the first girl to leave The Inferno. When she returned to the game eight years later, she excelled on the new Battle of the Seasons. This momentum didn’t sustain on Rivals 2 where she quit the game. Another eight years passed and she returned for All Stars. This time, she left early, but it was because she was the first person to lose the trivia challenge
Robin Hibbard (The Inferno 2 & Rivals)

On Battle of the Exes, Robin was self-aware enough to tell everyone her weaknesses lied in eliminations. There’s certainly evidence to back this up. She left Rivals on the first episode. Like Trishelle, she lasted four episodes on The Inferno 2, but she was the first girl to depart. On her later seasons she didn’t do much better in elimination, but she did beat Casey once.
Tyrie Ballard (The Inferno 3, Rivals, & Rivals 2)

The only name to appear on here three times, Tyrie has had a lot of misfortune in the game. On The Inferno 3 he was slated to compete against Davis but Alton replaced him thanks to a lifeshield. Rivals gave him a very physical elimination, which catered to his strengths, but he was attached to Davis. This allowed Wes & Kenny to defeat them. Finally, on Rivals 2, Dunbar lost on purpose and took Tyrie with him. Of all of the losses, that was the biggest slap in the face.
Chet Cannon (The Ruins & Free Agents)

On his debut season, Chet’s fate was predictable. He was the rookie, first man voted in, and lost to Wes. He would redeem himself a bit on later seasons, especially Battle of the Seasons, but he found himself back in the first elimination on Free Agents. He was randomly selected to be the captain of the losing team and this painted an easy target on the back. In the Balls In elimination he split his chin open on the face shield of his mask. He chose to remove himself from the game to avoid ripping his face completely open. After all, it was the first elimination. Even if he won, it would be weeks before he could properly stitch his chin closed.
Darrell Taylor (Fresh Meat 2 & Dirty Thirty)

Darrell has a reputation as one of the toughest competitors to ever play the game. Early in his career, he was also known as undefeated. Then, Fresh Meat 2 happened. He lost his first elimination and it was the first of the season. A poor showing, and it seemed like he was going to retire from the game on the bottom. Seven years later he returned to The Challenge on Invasion. He eliminated two champs and proved his value in the competition. Then, Dirty Thirty happened. He was purged out right at the beginning and never made it back into the house.
Derek Chavez (Cutthroat & All Stars 2)

Cutthroat was filled with rookies, but the Cancun cast we picked off particularly quickly. Derek lost to Brandon on the first episode alongside Emilee. On All Stars 2, he lost the first elimination again. Sadly, he may have needed to return home after his sister passed away immediately before the season started filming. If nothing else, he did better than Emilee by merely making the cast this season.
Jessica McCain (Rivals 2 & Battle of the Exes 2)

Much like many people on this list, Jessica was a rookie casualty on her first season. She tried, but her partner wasn’t in the right condition to excel on Rivals 2. After a big improvement on Free Agents, Jessica found herself in the middle of the rookie/ veteran split on Exes 2. This landed her in the first elimination and she lost to a newbie team. However, her qualification for this list depends on how you look at Exes 2. She did lose the first elimination, but she was sent to Battle of the Ex-ile. There, she beat Thomas & Hailey. Technically, she was the second female to be truly eliminated from Exes 2. To add another layer of complexity, she was part of the first team to truly leave Rivals 3 via elimination. This isn’t going to count because the first team eliminated was brought back due to some stupid luck.
Jemmye Carroll (Free Agents & Final Reckoning)

It kind of sucks for Jemmye to be on this list. She lost Free Agents to a rookie, and that was a fair loss. Granted, she was the first person to lose an elimination after flipping the kill card, but she had a fighting chance. That’s more than she can say on Final Reckoning. She was buried in a coffin and Jenna couldn’t unbury her fast enough. She then got purged out and couldn’t even compete to get back into the game due to the randomness of the Double Cross.
Devin Walker (Rivals 3 & Dirty Thirty)

Despite being eliminated first, Devin had some dumb luck on his rookie season. Too many people were quitting, so he was brought back to replace some of the lost teams. Don’t let his appearance in the final fool you, he lost the first elimination. Then, on Dirty Thirty, he was purged right at the beginning. On his first two seasons, he lost as soon as he could.
Ashley Mitchell (War of the Worlds & Double Agents)

It’s hard to deny Ashley’s success in the game, but it’s also hard to deny her target. After winning a million dollars on Final Reckoning, she was the first veteran eliminated on War of the Worlds. While some rookies left before her, the vets were immune from this. Then, on Double Agents she was a casualty of the first elimination. This time, the target was on her partner CT’s back, but a convenient twist sent girls into the first elimination. Fortunately, Ashley got back into the game. Unfortunately, she left shortly after.