Every Challenge Winners from the 30s Ranked

The Challenge has made it past season 39, and over the course of the past 10 seasons, we saw 19 Challenge championship titles handed out. It’s becoming increasingly difficult (and lucrative) to secure a win, but that doesn’t mean every victory is created equal.

Looking at the main series, I will be ranking every win from seasons 30-39 from least to most deserved. I’ll rank each win individually, so Jordan and CT will appear on here more than once.

What constitutes deserving? People who dominated in daily challenges and eliminations will get the most credit, but people with strong alliances or those who navigated the game by making smart moves that allowed them to avoid eliminations will also receive recognition. Competitors will be rated less-favorably if their victories relied on luck or if the “Challenge gods” (aka production and formatting) played critical roles in their victories.

19. Dee Nguyen (War of the Worlds 2)

It feels odd to look back at Dee’s time on The Challenge and acknowledge her for being successful, but she did win War of the Worlds 2 despite the odds being against her. However, she won few daily challenges and zero eliminations this season, and she mostly avoided elimination by crying to Rogan. There’s no denying her strategy worked, but is it noble? Not really.

18. Emanuel Neagu (Battle for a New Champion)

Emanuel’s win automatically gets dinged for being on a season without any Challenge champs, but the fact that he never went into elimination to “beat the best” makes it less notable. He mostly navigated the game by making alliances and avoiding targets by letting his allies do the dirty work. By the time he made it to the final, he was in a good position to win… because other people had taken out his biggest competition.

17. Rogan O’Connor (War of the Worlds 2)

After his early boot on Vendettas, it’s quite impressive to watch Rogan return and win during his second attempt at The Challenge. It’s also surprising that he was the only Brit to win on Team UK, but he was in that position because he never went into elimination. He played an undeniably strong social game, but by the time he was in the final, viewers still didn’t know if he could keep up with his team.

16. CT Tamburello (War of the Worlds 2)

Dad Bod CT was an odd period of Challenge history, but it felt like the odds were stacked against him when he was sent to Team UK on War of the Worlds 2. Fortunately, (and likely due to Kyle) he quickly became recognized as a team captain. He was able to avoid every elimination throughout the season and still posted a very solid performance in the final. While he did a stellar job navigating the competition, his performance in daily competitions left something to be desired.

15. Hunter Barfield (Final Reckoning)

Coming into the game late as a mercenary, there’s no denying that Hunter was in a good position on Final Reckoning. He had his entire Young Buck alliance and the Lavender Ladies on his side, so it’s not too surprising he made it to the final without seeing elimination. However, his victory is tarnished by the fact that he didn’t win any money. This can be attributed to his fairly sloppy run in the final where he just fell down the helicopter ladder, didn’t want to throw the grenade strategically, and just let Ashley outrun him.

14. Kaycee Clark (Spies, Lies and Allies)

Kaycee is a strong competitor, so it was no surprise that she made it to the end of Spies, Lies and Allies without much struggle. She did well in competitions, but her alliance protected her and Nany until the final. Her worst moments came during the final when she found herself in an elimination. Nany just rolled over and essentially quit so Kaycee could advance, and then Kaycee was granted CT as a partner because she won the elimination — a position she was in because of her poor performance.

13. Amber Borzotra (Double Agents)

Winning The Challenge as a rookie is no easy feat, and Amber is one of the few people who obtained the title on her first season. While the gold skull twist likely helped Amber survive in the game longer than other rookies, she did need to win two eliminations to make it to the end. While had the Big Brother alliance, they turned on her in the end — but it was CT who recognized her potential and wanted to run to victory with her.

12. Jordan Wiseley (Dirty Thirty)

Jordan is one of those players who always manages to impress in the game, and his victory on Dirty Thirty was no exception. While he did extremely well in the final, it took him a while to get his momentum in the daily challenges. He made some sloppy game moves, and he would have been eliminated before the final if it wasn’t for Nelson getting DQed, leading to two men returning from the third redemption challenge.

11. Tori Deal (Ride or Dies)

By the time season 38 rolled around, Tori established herself as a competitor with a lot of potential to win. She had many allies and excelled during a lot of the daily challenges, but this season really tested her on an emotional level. She made some questionable moves (especially once Jordan came into the game) that could have jeopardized her success, but in the end, she endured the 100-hour final and got her victory.

10. Devin Walker (Ride or Dies)

Arguably, Devin and Tori played very comparable games this season (they were partners, after all), but Devin had a few moments that impressed more than Tori. His knowledge helped the team win in the first Arena, his one-off alliances kept the team safe, and he helped reel Tori back into game mode during emotionally taxing moments.

9. Johnny Bananas (Total Madness)

Bananas had to overcome an alleged curse to win this season, but proved he still has the social prowess to make it to the end. He formed an alliance with his sworn enemy Wes to work together, and really, the numbers were stacked against the two. While the red skull twist may have made this game a little easier for the multi-season champ, there weren’t many areas where he could have done better.

8. CT Tamburello (Double Agents)

This season proved to be somewhat challenging for CT due to the partner rotation. After losing Ashley early into the game, he worked with Big T. Still, the pair managed to win a few times and CT was helping Big T improve. However, CT’s gold skull came to him suspiciously easily when he had the opportunity to call out Josh in a random double elimination, and he avoided the final elimination thanks to an uneven number of players. Luck was definitely on his side, but that doesn’t mean he didn’t need to put in a lot of work.

7. Ashley Mitchell (Final Reckoning)

Ashley is a smart, cunning player, and there’s no doubt she had her eyes on the prize this season. While she benefitted from working with Hunter, a player who complimented her skills well, her Lavender Ladies alliance played a major role in her getting to the end without seeing a real elimination. It seems like Ashely maintained focus during the final, while Hunter was a bit more reckless, allowing her to have the million-dollar decision and the biggest prize in Challenge history.

6. Jenny West (Total Madness)

Jenny is a physical specimen, and on a season with a red skull twist, it’s no surprise that players didn’t want to face her in elimination. While she quickly got a skull, her ability to win allowed her to keep it. She won a second elimination toward the end of the season when players smartened up and realized they might not want to see her in a final, but by that point, no one was going to keep her from winning.

5. Camila Nakagawa (Dirty Thirty)

With all of the controversy surrounding Camila this season, it’s easy to forget that she really had to fight to get to the end. She was one of the few people who never went to the redemption house, and she played a very unpopular game. Toward the end, she went into multiple eliminations and many girls were trying to get her out of the game. Despite this, she fought against the numbers and earned her place in the competition, eventually getting the grand prize… even if she wasn’t invited to the reunion to receive it.

4. Turbo Cambrian (War of the Worlds)

When Turbo won War of the Worlds as an unknown rookie, it felt like he did the impossible. He defeated a cast of established veterans, and he was never even sent into elimination. Of course, these vets spent the season taking shots at each other, allowing Turbo to fly under the radar, but his achievement is still incredibly impressive. He came across as a logical and likable winner, a reputation he would quickly lose during his subsequent Challenge appearances.

3. CT Tamburello (Spies, Lies and Allies)

CT’s time on Spies, Lies and Allies feels like a master class in how to use veteran status to win the competition. It almost came too easy to him, and it felt like no one was willing to take a shot at him. While he dominated many of the daily challenges, he did have a target from people like Devin who insisted they didn’t want a prior champ to win another season. Despite this, he skated to the end, solved every puzzle in the final, and made winning look easy.

2. Cara Maria Sorbello (Vendettas)

In a game as stupidly random as Vendettas, Cara Maria played as well as anyone could. She had allies and kept them close, didn’t overextend herself, and dominated many of the daily challenges. This allowed her to avoid every elimination (though she did get grenades thrown at her) because most people were scared of her wrath. Most impressively, she improved her puzzle abilities and won the season due to a puzzle, a skill set most people think can’t be improved.

1. Jordan Wiseley (War of the Worlds 2)

Jordan came into this season pompous, arrogant, and unafraid. While this landed him in a few eliminations, he was able to excel every time and inch his way to the final. This allowed him to be the star of the season, ruffle many feathers, exploit every twist, and still come out on top. Jordan may have been many things this season, but boring was not one of them.