OK, so no one on The Challenge really becomes rich. However, there are some people who have certainly turned their luck around. In this post I am going to look at people who finished in last on a Challenge then made it to the final on their following Challenge appearance. These Challengers have literally gone from the worst possible position to making money on their following Challenge. That’s certainly an improvement.
Robin (The Inferno 2- The Gauntlet 2)
After losing to Tina on The Inferno 2 and becoming the first female eliminated, Robin redeemed herself by coming onto The Gauntlet 2 and making it to the final. While the veterans did pretty terribly in the final, Robin did walk away with a pay check.
Johnny Bananas (The Duel- The Inferno 3)
After traveling to Brazil for about 45 minutes before getting eliminated, Johnny decided that he wasn’t going to let one last place finish stop his Challenge career. He returned to compete on The Inferno 3 and made it to the finals. While his team lost, he did walk away $10,000 richer.
Paula (The Duel- The Inferno 3)
After being the first girl eliminated from The Duel, Paula did receive recognition for her efforts against Aneesa in the Pole Wrestle Duel. She returned for The Inferno 3, made it to the final, and eliminated Aneesa. A very successful return even though she didn’t win.
Cara Maria (Fresh Meat 2- Cutthroat)
May it was just bad luck, but somehow Cara Maria and Darrell finished last on Fresh Meat. While this performance didn’t represent either Challenger well, Cara Maria struggled to redeem herself on Cutthroat. Fortunately, she was able to do it and made it to the final Challenger where she finished second.
Diem (The Ruins- Battle of the Exes)
It’s not like Diem to perform poorly on a Challenge, but that happened during The Ruins when she lost to Tonya. When she returned a few seasons later she was reunited to CT. The two nearly won Battle of the Exes but came in second during the final stretch.
Trishelle (The Inferno- Battle of the Seasons)
The biggest gap between Challenges proved to be a profitable move on Trishelle’s behalf. After being the first female eliminated on The Inferno, Trishelle waited 8 years before making her Challenge return. When she did, she made it to the final with her new friend Dustin and walked away with $25,000. Not first place, but not a bad payday either.
Now, we’re going to look at the truest rags to richest stories. These people finished last, returned to a Challenge and won.
Evelyn (Fresh Meat- The Inferno 3)
We all know Evelyn can help Paula win a Challenge, but there’s no saving Danny. When she was paired with him on Fresh Meat they were the first team eliminated. We saw the true Evelyn during The Inferno 3 when she was a force to be reckoned with. She made it to the final and won the whole thing alongside her Bad Ass team.
Rachel M. (The Inferno 3- The Gauntlet 3)
As someone who has competed on only 2 Challenges, Rachel has seen the best and the worst of the Challenge world. She had an embarrassing loss on The Inferno 3 where she was the first female to go home. On The Gauntlet 3 she was able to fly under the radar and make it to the final. She didn’t do much memorable on The Gauntlet 3, but she did win.
Wes (Battle of the Seasons- Rivals 2)
Wes’s Challenge career started a slow decline after winning The Duel. He declined so much that he was the first person eliminated from Battle of the Seasons. This loss didn’t slow him down because he returned to Rivals 2 and was able to redeem himself. He made it to the final with his partner CT and they walked away with the gold.


I do not know if this counts but CT DQ’ed on the Inferno 3 being sent home first then made it to the end of the Gauntlet 3 even though he did not make any money.
I chose not to count CT because his DQ could have been prevented.