Over the years, The Challenge has grown from a show that featured The Real World and Road Rules stars battling it out into a free-for-all that includes some of the most over-the-top and intense competitions on television.
The stakes are high, and the drama is even higher, which has been what has fueled the MTV reality series for nearly a decade now. Also over this time, there have been a number of challengers who have amassed quite a lot of wealth in competing for glory. Some contestants have gone on to earn a ton while on The Challenge, and a new Challenge legend has finally taken the top spot.
Updated on January 9th, 2022 by Hilary Elizabeth: Who has won the most money on The Challenge? Because The Challenge is a hit series that shows no signs of stopping and the money that the show offers seems to increase every single season, the biggest victors in Challenge history seemingly change on a nearly constant basis.
15 Darrell Taylor – $248,055
The fact that Darrell makes it onto the list of top earners at all is a true testament to what an incredible competitor he is, because the last time that he actually won The Challenge was in the original Fresh Meat that aired in 2006.
That season is actually where the bulk of his prize money came from, but that was also his fourth Challenge win in four seasons, meaning that he literally won every single season he appeared on prior to his biggest win as well.
14 Rogan O’Connor – $250,000
Rogan O’Connor actually only has one win under his belt, but he was lucky enough to get his Challenge championship in a season that had a pretty great winning pot.
He won alongside Team UK in War of the Worlds 2, and as the final prize money was a cool million dollars, this four-person team split the cash and they all added themselves to the list of highest-earning winners in the history of The Challenge.
13 Dee Nguyen – $255,000
Before she was fired from The Challenge for her controversial Black Lives Matter comments, Dee Nguyen was a money-earning machine on the show with the potential to have a very profitable Challenge career.
She amassed a total of $255,000 from the series, with a big chunk of that money coming from her win on Season 34, War of the Words 2. If she was still on the show, there wouldn’t be any doubt that she would move up higher on the list.
12 Wes Bergmann – $303,000
Some may find it preposterous that Wes ranks so low on this list, especially due to his near-mythical legend on The Challenge. However, while he has certainly cemented his reputation as a proven winner, he hasn’t nearly racked up the money as other seasoned veterans have done.
Although Wes himself will shamelessly admit that he’s rich, he hasn’t earned as much as many other Challenge competitors simply because many of his wins came earlier on in the series, when the cash winnings were only a fraction of what they’ve become in later years.
11 Kaycee Clark – $403,ooo
Although Big Brother alum Kaycee Clark only made her debut on The Challenge three seasons ago, it seemed like it was only a matter of time before she became a champ. She made it to the finals in both Total Madness and Double Agents, and she finally won the latest season, Spies, Lies, and Allies.
And, Kaycee could have actually bumped herself up a few notches in terms of winning, as the prize for the season was a million dollars, and it was up to the winners to decide whether or not to share with the other contestants. Kaycee and CT chose to give the other teams $100,000 each.
10 Amber Borzotra – $455,000
Amber Borzotra was consistently on the bottom of the Big Brother alliance during Double Agents, which is ironic considering that she went on to win the entire season and nearly half a million dollars. Her first win also came during her debut season, making it all the more impressive.
She didn’t perform as well on Spies, Lies, and Allies, however, given that she can run faster and further than a gazelle, her chances of winning a final should she make it to one are extremely high.
9 Jenny West – $500,000
Although Jenny West has only appeared on two seasons thus far, absolutely no one was surprised when she won Total Madness and the half-million-dollar prize that came along with it.
The minute that Jenny showed up on War of the Worlds 2, the competitors were intimidated, because they have eyes and could see that Jenny was arguably the physically strongest female Challenger of all time. And if she ever returns to the series, it wouldn’t be surprising to see her add some championships to her resume.
8 Yes Duffy – $511,254
When Paramount+ announced the first season of The Challenge: All Stars, fans were wondering how the cash prize would measure up to the mainline series. And, viewers were not disappointed when TJ announced that the final win was worth $500,000.
Understandably that amped up the competition, and dark horse Yes Duffy wound up taking the grand prize. Prior to his win, Duffy hadn’t appeared on The Challenge since the original Battle of the Sexes season in 2002.
7 Camila Nakagawa – $561,250
From the moment she was introduced on The Challenge, Camila Nakagawa made it clear that she was a force to be reckoned with. But she really began making a name for herself on the series in a big way in her later seasons.
Her biggest win came in the 30th season, aptly titled Dirty 30, when she came in first place and scored $450,000, making up the bulk of her Challenge bank account. Dirty 30 was also her last season.
6 Cara Maria Sorbello – $602,250
There have been many impressive women who graced The Challenge, but few have been as dominant as Cara Maria Sorbello. Her winning account grows with each Challenge, with her biggest gross coming on Season 31 (Vendettas) when she banked over $378,o00 on her way to winning the season.
Season 27 (Battle Of the Bloodlines), in which she won over $125,o00, was another big one. She’s a regular powerhouse in The Challenge, despite the fact that she ironically was considered a weaker competitor when she first began appearing on the show.
5 Turabi “Turbo” Camkiran – $750,000
As time has gone on, the final prize money on The Challenge has grown exponentially, which is how someone like Turbo can make the top 10 winners despite only winning one season.
Many Challenge fans are hoping that Turbo will return to the game at some point, as his performance in War of the Worlds was dominant and incredibly impressive. He also single-handedly won $750,000 for his trouble, which seems like a pretty solid incentive to give the competition another chance.
4 Jordan Wiseley – $833,000
Jordan Wiseley is pretty notorious for his incredibly arrogant attitude on The Challenge, but no one can say that he doesn’t have the record to back it up.
Jordan has taken a bit of a break from The Challenge (on account of his breakup with Tori Deal), as he hasn’t competed since season 35, Total Madness. But the intimidating amount of his cash winnings comes as no surprise either, because Jordan has been on six seasons of The Challenge so far and has won four of those seasons.
3 Ashley Mitchell – $1,121,250
Viewers first saw how good Ashley Mitchell was in Season 29 (Invasion), in which she went all the way and won the season.
To cement her place as a dominant player in The Challenge, she won the $1 million prize in Season 32 (Final Reckoning). Her willingness to steal half of the prize money from her partner in Final Reckoning has made it more difficult for Ashley to go further in the game, but she still has a shot of bulking up her bank account.
2 Johnny “Bananas” Devenanzio – $1,184,720
There is no denying that Johnny Bananas sits on a throne all his own in The Challenge. Although Johnny doesn’t have the best elimination record, he’s borderline impossible to beat if he can make it to a final.
Bananas has also appeared on an astounding 20 seasons of the series, meaning that he’s been on more than half of the Challenge competitions total. Given how many opportunities he’s had to win, it comes as no surprise that he occupied the top winning spot until finally being usurped recently.
1 Chris “CT” Tamburello – $1,365,000
CT had a pretty rocky start on The Challenge, despite the fact that he had everything he needed to win from the very start. However, his hot temper got the best of him, and it took him ages to finally become a Challenge champ.
Tamburello has certainly made up for lost time though. As of the latest Challenge season, Spies, Lies, and Allies, Chris finally overtook Bananas in terms of winnings and bumped him from the top spot that he had occupied for many seasons to become the contestant who on the most money on The Challenge.
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