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 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. So, who has won the most cash on The Challenge? These are the top Challenge winners, along with their total winnings.
Updated on January 10th, 2022 by Hilary Elizabeth: The Challenge players with the most final challenge prize money is a ranking that's changed over the years with the show's expansion. One thing that's remained the same is that fans are always wondering who won the most money on The Challenge.
Darrell Taylor - $248,055
Darrell was an incredibly dominant player in the early years of The Challenge, and his record still shows it.
Despite the fact that the cash prizes in the early years of the series pale in comparison to some of the current final challenge winnings, Taylor still manages to crack the top earners in Challenge history. That's likely on of the fact that he won the first four Challenges that he competed in, an astonishing record for the reality TV show.
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 being eliminated in the first daily challenge on Vendettas, Rogan returned and won War of the Worlds 2 by aligning with Paulie and Cara's alliance that kept him out of elimination the whole season.
Although his winnings are impressive, his inclusion is more indicative of how the prize money has grown as The Challenge has changed.
Dee Nguyen - $255,000
Dee has appeared on two seasons and performed relatively well in both. In War of the Worlds, 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. However, given that MTV publicly cut ties with Nguyen, it looks like this money will have to tide her over for good.
Wes Bergmann - $303,000
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' appearances on the series have been intermittent due to his business, there is no telling if he will be able to achieve any more substantial paydays before he leaves The Challenge for good.
Kaycee Clark - $403,000
Although the Big Brother alliance has become a bit of a juggernaut in the past few seasons of The Challenge (to the frustration of some fans), luck hasn't been on their side when it comes to actually winning until recently.
Amber Borzotra was the first BB alum to win, but Kaycee finally won this season of Spies, Lies, and Allies, putting her on the map as one of the highest earners in the history of the show.
Amber Borzotra - 455,000
CT might just be the good luck charm that Big Brother players need to win The Challenge, as Kaycee won her first Challenge partnered with CT in Spies, Lies, and Allies and Amber won her first Challenge partnered with CT in Double Agents.
And fascinatingly, in both seasons Amber and Kaycee hadn't been partnered with CT at all, only to win it all with him in the final. Apparently, it's a strategy that pays off for them, literally.
Jenny West - $500,000
Some players come on The Challenge to make a name for themselves on social media. Some of them are cast simply because they make for outrageous TV.
And some of them, like Jenny West, are invited to appear on the series because they're incredible competitors. Jenny is undoubtedly one of the best athletes to ever The Challenge, and although she has only been on two seasons so far, she definitely earned her half-million win.
Yes Duffy - $511,254
The winner of the first season of The Challenge: All Stars, Yes Duffy hadn't even been on the show in more than a decade and a half when he decided to return.
And the competitors on All Stars were no slouches either, they certainly lived up to the title of the show and some of them were even still competing and killing it on the main series, meaning that Yes really earned the money that he won for the season.
Camila Nakagawa - $561,250
Camila hasn't competed in The Challenge since winning The Challenge XXX: Dirty 30, but she still ranks with money won from her two victories. Camila won both Dirty 30 as well as Battle of the Exes II while partnered with Johnny Bananas.
Unfortunately, Camila'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, Camila hasn't and will most likely never return to the show. She probably ends her career winning $561,250 in final prize money.
Cara Maria Sorbello - $602,250
The most recognized woman 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. She won with a partner on Battle of the Bloodlines and had a historic win on Vendettas when she became the first individual female player to win a season. Always the constant underdog, Cara Maria garnered the favor of fans by constantly proving 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 on an indefinite Challenge hiatus, a much-needed break to hopefully help her reset and return stronger than ever.
