The Challenge

10 Messiest Challengers Who Became Champions

These people played a messy game, but went home with a big paycheck.

Some people believe you need to bring your A-game to win The Challenge. That’s not true. Some competitors bring a lot of baggage and start unnecessary drama, but in the end, they leave the game as a champion.

What constitutes a “messy” Challenger? Usually, it’s someone who starts a lot of fights, gets involved in romances that negatively impact their game, and makes poor political moves that have repercussions later on. At some point throughout the season, they lose sight of the end goal and get involved in heat-of-the-moment mistakes — but in these cases, they collect themselves before the end of the season to get a win.

You’d never want to model your game after these people, but production loves them. They gave us seasons filled with interesting storylines that kept us on the edge of our seats. And just to be clear, I am only assessing people based on the season they won — past and future messiness won’t be taken into account.

10. CT Tamburello (Rivals 2)

Many people celebrate this season as CT’s big win and a turning point in his Challenge career, but there was a lot of drama leading up to the championship. He got into a fight with Marlon on night one, and after the first challenge, he was plotting to get Bananas thrown into the first Jungle. Plus, he hooked up with a lot of females in the house, like Anastasia, Cooke, and Nany. The arguments continued throughout the season, including scuffles with Frank and Bananas, but this never derailed CT. He seemed to cause issues, run away from the mess, and carry on like nothing happened.

9. Tori Deal (Ride or Dies)

There’s no doubt that Tori worked on bettering herself prior to Ride or Dies, and she was open about the fact that she benefitted from therapy and anti-depressants. Then, Jordan showed up, and we started to see a messier side emerge. She started rekindling things with him, only to watch him develop feelings for Nurys. They tried to keep their personal lives separate from the game, but Tori eventually brought their relationship into the game for the sake of keeping Faysal safe. Ultimately, Jordan protected her, but she did get called a terrorist and got into multiple arguments with her ex-fiancé. And despite this, we all know it could have been much worse.

8. Katie Doyle (The Inferno)

When you watch the first few episodes of this season, it’s pretty obvious why the Road Rules team wanted Katie gone. She believed the Real World team would always save her, so she took it easy in missions. After that, the Roadies realized they’d need to employ the Lifesaver to get Katie into The Inferno. As a result, Katie spent a lot of time arguing with her teammates, and they spent a lot of time planning to get Katie in another Inferno. But, Katie persevered. She won two Infernos and helped her team get handsomely rewarded.

7. Ashley Mitchell (Invasion of the Champions)

It’s hard to believe Ashley walked into this season with very few relationships because she walked out of the house with three best friends and dozens of enemies. Ashley began this season by hooking up with Hunter, a fling that would quickly end and result in tension on the team. She’d also find herself antagonizing the veteran girls with Amanda and threatening to quit multiple times. One time, she had her toilet seat sent to sea and the second time, she had her ticket to the final but felt lonely in the house. Luckily, she pushed through because she has the ability to forget about drama really quickly when she’s chasing money in the final.

6. Jordan Wiseley (War of the Worlds 2)

Jordan has always been a cocky player, but his ego got a lot bigger after winning Dirty Thirty. On War of the Worlds 2, he wasted no time drawing a line in the sand and dividing Team USA. He continued to butt heads with his teammates, even getting into an argument with Turbo that resulted in Turbo’s departure. Then, he won an elimination, proposed to Tori, and switched to Team UK. All of these grand actions should have ruined his game, and being on Team UK guaranteed he’d see more eliminations before getting to the final. But, he managed to keep winning, and the winning streak continued through the end of the season.

5. Hunter Barfield (Final Reckoning)

Hunter’s always been a hothead, and he’s particularly susceptible to making dumb choices when Team Young Buck is involved. During this season, Hunter argued a lot with his partner Ashley, which you’d kind of expect. But, after he found out Ashley hooked up with Kyle, he slut-shamed her and threatened her family while venting to his friends. When Ashley heard these words, they stung deep, and Hunter’s continued bickering did nothing to help his case. So, when Ashley had the power to take Hunter’s money, she quoted his threat and took $500,000 out of Hunter’s pocket.

4. Frank Sweeney (Battle of the Seasons)

It’s shocking to see how connected Frank was coming into this season, given the fact that he’d never done a season before. But, a lot of those relationships were fragile and we watched him get into many fights this season, like with Alton and Marie. Worst of all, his argumentative nature bled into his team dynamic, and he even had Zach cursing his name toward the end of the season. His worst showing came during the final when he shoved Sam; minutes later, he crossed the finish line and Team San Diego won the grand prize.

3. Johnny Bananas (The Island)

I’m very forgiving for the sins people committed during The Island, but in a house of 20 crazy people, Johnny’s antics were the worst. He was rude toward the women and insulted them under the veil of humor. If you watched the season, Evelyn took this very personally which caused her to steal Johnny’s key. But, at the eleventh hour, the two enemies made a deal. They both won, but it did a serious number on his relationship with Paula, one of his best allies up to that point.

2. Cara Maria Sorbello (Battle of the Bloodlines)

It took Cara Maria eight seasons to finally get a win, but her biggest obstacle on Bloodlines was the drama the season brought. At first, she was flirting to get allies and build relationships, but this went haywire when Abe showed up. Suddenly, she had to deal with the backlash of her flirtatious gameplay, and exploiting this secret became part of Bananas’s gameplay. Winning this season brought Cara Maria closer to her cousin Jamie, but it put major strains on other relationships.

1. Camila Nakagawa (Dirty Thirty)

The most surprising thing about Camila winning Dirty Thirty: She got to stay until the end. Throughout this season, she burned many bridges, went on a racist rampage through the house, threw a dumbbell at production, and made out with Tony on a bus. It felt like the majority of the cast avoided Camila because she surrounded herself with chaos, and in the end, she went home with the grand prize — even though she wasn’t welcome at the reunion.

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