Top 10 Challenge Contestants We Want to Get Their First Win

MTV’s The Challenge is unlike any other reality show. Most reality shows feature a new cast of contestants every season with an “All-Stars” cast, consisting of memorable characters appearing every few years. The Challenge, on the other hand, is basically an All-Stars show. Rather than beginning every season with a cast full of new players, almost every season begins with people playing for their fifth, sometimes eighth, and even fourteenth times. The person that holds the Most Appearances record has been on TWENTY times over the course of fourteen years. Being on season after season does not guarantee success though. Here are the Top 10 Challenge Contestants We Want to Get Their First Win!

Note: To be included on this list, the contestant had to have appeared within the last five seasons (Final Reckoning – Double Agents). If we opened it up to anyone from the franchise, it would be a more complete, but much longer list. These people are more likely to come back and we could realistically see them cross the finish line in the coming years.


10. Kam Williams

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 5

Most Recent: Double Agents

Highest Placement: Eliminated during the Final (Vendettas/War of the Worlds 2)

Love her or hate her, every Challenge fan has an opinion about Kam Williams. Since her debut on The Challenge: Vendettas, Kam has proven to be a force to be reckoned with. During her first season, Kam won three elimination rounds and even made it all the way to the final. Unfortunately, she was eliminated before finishing the final. When she appeared on War of the Worlds 2, she had the same fate.

Although Killer Kam has yet to get the win, she is trying her very hardest. With an elimination record of 6-1, she does a good job at making it far each season but just needs the extra push to get the money. On the current season, Double Agents, Kam seems more determined than ever. With her boyfriend, Leroy, Kam has been on a mission to get out anyone who has previously won the game. Will it work out for her? Only time will tell. We do know that whether you like her or not, after hearing her story about her childhood and familial background, it would be an exciting moment to see her pull it off. She wants it more than anyone else, it’s just a matter of making it happen.

9. Sylvia Elsrode

Number of Appearances: 3

Most Recent: Final Reckoning

Highest Placement: 2nd Place (Final Reckoning)

Sylvia is one of the most underrated competitors in recent years. Sylvia has always been underestimated by her fellow competitors. She is usually sent in to elimination early on in the season and she usually returns to the house after eliminating her competition. Despite being on only three seasons, Sylvia has a 5-1 elimination record. Her wins are against some solid competitors too – Kailah, Johnny Bananas, Tony, and Tori.

The last time we saw Sylvia, she made the final of Final Reckoning, where she ended up in 2nd place with her partner, Joss. Their 2nd place finish this season is quite controversial, actually, because the winners of that season didn’t even join the cast until almost halfway through the season. Sylvia and Joss had been there since the beginning, fought their way to the end, and lost to Hunter and Ashley “Millionaire” Mitchell. While their win did make for an iconic moment, it came at the expense of the true winners of that season. Hopefully, the Kansas City Queen will return to The Challenge soon so that she can continue proving everyone wrong and get her first win.

8. Aneesa Ferreira

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 14

Most Recent: Double Agents

Highest Placement: Runner-Up (The Gauntlet 2), 3rd Place (The Duel II)

Aneesa holds a notorious title. She holds the record for highest number of appearances without winning. Aneesa began her Challenge career during the 6th season of the show, which premiered in 2002. As of this writing, Aneesa is appearing on her 14th season of The Challenge and is still hoping to get her first win.

Across her fourteen seasons, Aneesa has seen twenty elimination rounds and has won half of them. While a 50/50 record is not the most impressive, what is impressive is that she is continuing to do it. A lot of impressive competitors lose some of their mojo over the years. Aneesa, on the other hand, just won an elimination round this season. She is more determined than ever to win and seeing her get her first win would be a great moment in Challenge history.

7. Leroy Garrett

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 12

Most Recent: Double Agents

Highest Placement: 2nd Place (Battle of the Exes II)

The male counterpart to Aneesa, Leroy has participated in eleven full Challenge seasons without winning. During his rookie season, Leroy made a splash by making the final with his partner, Mike Mike, who is maybe the most regular guy to ever appear on the show. The duo got third place and kickstarted Leroy’s losing streak.

Since then, Leroy has made four finals, has won eight elimination rounds, and has had the misfortune of being DQ’d in two separate seasons. Leroy has been one of the more likable contestants since he started appearing on the show. He is nice to his castmates, rarely gets in fights, and just seems happy to be there which makes it easy to see why he is one of the top Challenge contestants we want to get their first win. However, he doesn’t always seem to have the drive to get that win. He puts his game face on when his back is against the wall in elimination, but beyond that, he is usually a pretty passive player. If he can find that motivation to win, he will cross the finish line soon.

6. Tula “Big T” Fazakerley

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 3

Most Recent: Double Agents

Highest Placement: 20/28 (Total Madness)

Big T is the biggest breath of fresh air to this franchise in quite some time. Unlike most of the contestants, Big T is not particularly physically imposing. In fact, she is one of, if not the, smallest contestant on the current season. What makes her stand out though is her personality. Big T is incredibly funny. She is entirely unique and it is clear how loved she is in the house. Most recently, we saw her win a daily challenge on Double Agents and were treated to a segment of her reveling in her win.

She was bragging about being the winner, she was telling everybody that they weren’t safe and that no one was, and she literally set up her own VIP area at the bar, where she held meetings and asked people to kiss her hands. During all of this, the other contestants were laughing. They were fully playing along and seemed so happy to be a part of Big T’s celebration. It was one of the best segments of the season so far.

That’s what makes the difference between her and most. The love that the rest of the cast has for Big T is infectious and she has made a big impression during her short time on the show. Seeing her get her first win would be one of the biggest underdog stories and couldn’t happen to a more fun Challenge contestant.

5. Theresa Jones

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 7

Most Recent: Double Agents

Highest Placement: 2nd Place (Battle of the Exes II)

Before Theresa’s current appearance, the Fresh Meat contestant left the show as she was hitting a stride in her career. After just missing out on the final in Free Agents, Theresa returned during the next season, where she ended up reaching 2nd place. After that, Theresa vanished. She hadn’t appeared in anything Challenge related for years and it looked like we’d never see her win. That is until just recently. She has made her grand return in the current season, Double Agents.

Although her return has been pretty quiet so far, there is still plenty of time in the season. Maybe she is just getting used to being back in the environment and we will really see her come out of her shell in the coming episodes. Seeing Theresa, who has always been a solid competitor, come out on top during her comeback season, would be a great way for the season to go. If she continues her losing streak, fingers crossed that this won’t be the last we see of her. Fingers doubly crossed that there won’t be another five year gap between appearances.

4. Tony Raines

Number of Appearances: 6

Most Recent: Final Reckoning

Highest Placement: Eliminated during Final (Vendettas)

If you had told me during, literally any of his first few seasons, that I would be rooting for Tony Raines to win, I would think you were crazy. In his very first episode on the show, Tony physically fought his teammate for the season, who happened to be his brother, Shane, and hooked up with Christina, while having a pregnant girlfriend at home. He then capped off his run that season by being sent home on episode four, due to rupturing his spleen during a challenge. His next few seasons went about as well as his first. Getting disqualified for fighting and being eliminated early became common trends for Tony.

The Challenge: Vendettas marked a turning point for Tony. This season Tony came back, fully committed to his relationship, fully committed to sobriety, and fully committed to winning. We saw a totally different side to Tony, as he began focusing on what he came to do and was playing for himself rather than showing up just to party. He dominated the season, winning 7/13 of the daily challenges, pulling off an enormous blindside on the show’s biggest character, and making the final. His journey across this season is one of the best redemption arcs in the show’s history and could have only been better if he had pulled off the win in the end. Hopefully he returns to The Challenge soon and gets his first win.

3. Da’Vonne Rogers

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 2

Most Recent: War of the Worlds

Highest Placement: Eliminated right before the Final (War of the Worlds)

Da’Vonne is a star. That much has been clear since her short lived run on Big Brother 17. Luckily, the producers saw something in her during her first few weeks in the Big Brother house and brought her back the next season, which then turned into her being one of the first few Big Brother crossovers on The Challenge. Big Brother might be where Da’Vonne started but The Challenge is where she thrives. Let’s be honest, the usual suspects that we see every season are not the smartest people in the world. And that’s by design. The show really highlights drama, hook-ups, and physically plowing through every other contestant in your path to win. And it often pays off for people who are just physical steamrollers. But then you have people like Da’Vonne, who are more than just physical competitors.

Da’Vonne is one of the more well rounded competitors in recent seasons. She is not built like some of the Olympian-like competitors we have seen recently but she is a physical force. Da’Vonne is also very aware of her surroundings. She is always paying attention to her competition and trying to find the best way to find an in with the people that she needs to be in with. If she decides to come back in the future, and can build up her endurance, watching her finally come out on top during a reality show, knowing that she will be able to provide a better life for her daughter, would be incredibly satisfying.

2. Kyle Christie

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 6

Most Recent: Double Agents

Highest Placement: 2nd Place (Total Madness)

Kyle represents a different kind of Challenger. Just about everyone on this list is known for their physical abilities. Kyle, on the other hand, is known for his social and strategic abilities. Kyle, in a word, is sneaky. Since his debut on The Challenge: Vendettas, Kyle has consistently managed to snake his way through the first half of the game easily. His secret weapon? He is a good liar. He knows this and takes advantage of it.

Despite knowing how he plays, people often keep him around because he is just so likable. He’s funny, is rarely involved in drama (that’s not Cara/Paulie related, anyway), and it seems that most of his fellow castmates just genuinely like being around him. Even though his strengths lie in his social and mental game, don’t underestimate Kyle in eliminations.

1. Nelson Thomas

Photo Credit: @ChallengeMTV on Instagram

Number of Appearances: 7

Most Recent: Double Agents

Highest Placement: 2nd Place (Invasion of the Champions)

Nelly T is one of the best current Challengers. He is so earnest in his affection for his friends and we would all be lucky to have a friend like him. Nelson is also one of the best players in elimination. His current record is 9-4-1, with that 1 being the one and only draw to be called during an elimination.

Despite being a fantastic competitor, he never takes himself too seriously. He genuinely looks like he is having the time of his life every time he’s onscreen and that quality is not always common among contestants. The best part about Nelson? He has the “ordacity” to mispronounce every other word in his sentences and still comes across as endearing. He is the top Challenge contestant we want to get their first win because we know that he would be so grateful for TJ to declare him as #1, it would surely be an emotional moment.

Want more Challenge Scoop? Then check out these articles!

Interview with Paulie Calafiore

Top 10 MTV ‘The Challenge’ Contestants We Want to Return

Interview with Jenna Compono

Interview with Kam Williams

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    1. @Bill Czachor, 1) It’s Double Agents, not Dual Agents. 2) What does being black have to do with it? Kyle, Theresa & Tony are not black, yet they miraculously made the list! Not to mention it’s great seeing more diversity in the cast!

  1. This is stupid as if Leroy isn’t #1 😂 he’s been on it about the longest of them all and such a great person. Also nobody is rooting for Nelson, Tony or Kyle..all are man whores and very disrespectful to woman. Same with Kam and Big T, all the new people need to sit down.

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