Debuting in 1998, MTV's The Challenge has been a mainstay of the network's programming for over twenty years. Originally pitting contestants from the networks other two popular reality shows, The Real World and Road Rules, The Challenge has grown to include members of other MTV shows as well as other reality shows, both domestic and abroad. As the cast has changed, the competition has become more grueling. Now, contestants endure physical, mental, and sometimes emotional challenges to achieve victory.
As the show has changed, so has the prize money. In season one, Road Rules: All-Stars, each member of the winning team was awarded a trip for two to Costa Rica. In contrast, the most recent season awarded $250,000 to each winner. So, who has won the most prize money on The Challenge? Here is the list of the top 10 contestants and their final prize totals.
10 Rogan O'Connor - $250,000
Rogan has the unique distinction of being the first British born competitor ever eliminated from The Challenge and the first to ever win it. After passing out in the first daily challenge on Vendettas, Rogan returned and won the shows most recent installment, War of the Worlds 2, by aligning with Paulie and Cara's alliance that kept him out of elimination the whole season.
Rogan has yet to face elimination, so time will tell if his place on this list will improve. His inclusion is more indicative of how the prize money has grown as The Challenge has changed. For comparison's sake, Darrell Taylor has four wins under his belt, but only $240,000 to his name.
9 Dee Nguyen - $250,000
The other recent addition to this list, Dee is technically tied with Rogan for the amount of money won. Dee has appeared on two seasons and performed relatively well in both. In War of the World, Dee was paired with Wes for the first half of the game which allowed her to build strong relationships with her fellow contestants before being eliminated just before the finale.
Returning for War of the Worlds 2, Dee used these relationships, along with a newfound romance with Rogan, to navigate her way to the end and win her first final. Unlike Rogan, Dee has been more battle-tested with elimination and has good relationships with fellow contestants. She has a good shot of increasing this total in the future.
8 Wes Bergmann - $298,000
For someone who is considered one of the faces of The Challenge, it is slightly shocking to see Wes so low on this list. This, however, has more to do with Wes's manipulative strategy and not his skill set. Wes is constantly scheming, which has helped him secure two victories but has also gotten him into countless eliminations.
Wes's first win came during The Duel, all the way back in 2007, while he partnered with CT to win Rivals II. Considering Wes only recently returned from a four-year absence from the show and he has business he is heavily invested in, there is no telling if he will be able to achieve any more substantial paydays before he leaves The Challenge for good.
7 Chris "CT" Tamburello - $514,750
With his recent win in War of the Worlds 2, Challenge favorite and resident dad CT earned his third win. A lot has changed in CT's life over the years, but his presence is still feared by his fellow contestants. Heck, even the producers still paint CT as a physical threat and routinely show the clip from Cutthroat of CT carrying Bananas like a backpack during an elimination.
Despite not being in the best shape of his life anymore, CT has managed to win two of his three titles in the last three years. As he gets older and his family grows, CT train is starting to run out of coal, but hopefully, he gets a few more shots to increase his prize totals.
6 Camilla Nakagawa - $561,250
Camilla hasn't competed in The Challenge since The Challenge XXX: Dirty 30, but she still ranks sixth with money won from her two victories. Camilla won both Dirty 30 as well as Battle of the Exes II while partnered with Johnny Bananas. Short in stature, Camilla competes using her fiery temper and surprising athleticism.
Unfortunately, Camilla's partying tends to get the best of her. On Dirty 3o, she unleashed a drunken, racially infused tirade directed at Leroy. This did not sit well with contestants and fans alike. Rightfully, Camilla hasn't and will most likely never return to the show. She ends her career winning $561,250 in final prize money.
5 Cara Maria Sorbello - $602,250
The most recognized female in Challenge history, Cara Maria has been a staple of the show ever since debuting on Fresh Meat II. She has competed in a total of fourteen challenges, winning two. Like many on this list, she won with a partner on Battle of the Bloodlines and individually on Vendettas. Always the constant underdog, Cara Maria garnered the favor of fans by constantly proving to other competitors how good she is.
Cara's fan following has slowly whittled away the last few seasons, however, as she aligned and began dating disliked Paulie. During War of the Worlds 2, Cara's attitude towards several of her fellow castmates became toxic and mean. Cara is not returning for season 35, a much-needed break to hopefully help her reset and return stronger than ever.
4 Johnny "Bananas" Devenanzio - $682,793
No one has competed in or won more Challenges than Johnny Bananas. With six total wins to his name, Bananas is in a class all of his own. He is an adept strategist that is willing to do anything to win the game. Nevertheless, he still only manages to crack the top four of all-time final winnings.
Bananas' earlier challenge career was riddled with early exits before he was able to secure his first victory on The Island. Since then, he has become the player best associated with the show. Bananas last win came on Rivals III where a twist allowed him to steal all the prize money from partner Sarah. Many believe Bananas is cursed for stealing the money. Nevertheless, there appears to be no end in sight for his Challenge career, so he is likely to add money to his overall total.
3 Turabi "Turbo" Camkiran - $750,000
Everyone's favorite Turkish challenger, Turbo comes in third on this list thanks to a large payday from his only win on War of the Worlds. Little was known about the Survivor transplant, but Turbo quickly garnered the respect of his fellow challengers with his athleticism and commitment to winning. Plus, you could always count on him for a funny line or two.
War of the Worlds II didn't fare as well for Turbo, who was kicked off the show for threatening Jordan and production security. With an acting career, there is no telling if we will see Turbo return anytime soon.
2 Jordan Wiseley - $833,000
Jordan is one of the most gifted athletes to ever appear on the show. Born without a left hand, Jordan is a beast at eliminations, amassing seven wins in nine elimination rounds. In five appearances on the show, Jordan has made a final four times, winning three of them.
Jordan's athleticism should allow him to add more money to his total in future seasons, but his attitude may limit this somewhat. His arrogance is a constant annoyance for his fellow challengers, and he has frequently been targeted for it. Still, few have dominated the way he has.
1 Ashley Mitchell - $1,121,250
Ashley is the only member of the millionaire club on this list. This is made even more impressive considering she has only won two challenges. After winning the female title on Invasion of Champions, Ashley went onto finish first on Final Reckoning. Like Bananas before her, Ashley was given the chance to take the whole one million dollar prize for herself and choose to leave partner Hunter with nothing.
Also like Bananas, Ashely hasn't won a challenge since stealing the money. Ashley displays surprising athleticism and is a good strategist. At times, her in your face personality gets her into hot water which will always hold her back. Ashely doesn't seem like she will be ending her Challenge career anytime soon, though her legacy is fairly cemented at least in terms of prize money.
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