The 10 Best Challengers to Have Not Won a Season(yet)

Henry L DiMaria
9 min readJul 28, 2021

Through the years of the Challenge there are plenty of competitors who have been top dogs or even dominant in seasons but some of them have still not taken home a win at the end. Some still have the chance to get that monkey off their back while others have “retired” from the show. So in honor of Leroy, who may just be on the list, officially “retiring” at the end of last season I have compiled my list of the best players that have not won a season of The Challenge.

Honorable Mentions:

Theo Campbell, Nelson Thomas & Joss Mooney

Nicole Zanatta, Ruthie Alcaide & Jenna Compono

5.

Shane Landrum

Original Show: Road Rules: Campus Crawl

First Season: The Challenge: Battle of the Sexes (Season 6)

Best Finish: 4 The Challenge: Battle of the Sexes

Average placement: 7.71

Elimination Record: 3–4

Shane is without a doubt a polarizing figure for many Challenge fans but it would be remiss to not have him here. Shane has proven to be a strong daily competitor, he has very good endurance, he is a smart player who has done well in puzzles and Shane is a good strategic player being the brains behind the Lavender Ladies alliance. If he were to get to a final I think he would be a massive threat to take it down. Shane has two sizable weaknesses that have held him back. First, Shane is not particularly strong in the physical eliminations but even then his losses are to good competitors like CT, Cory, Jordan and Wes & Casey. Secondly, it is unlikely for Shane to go under the radar he is bound to be a target over other people in his alliance because he is a hothead and frequently gets in fights with the other side of the house.

5.

Diem Brown

Original Show: The Challenge: Fresh Meat (Season 12)

First Season: Fresh Meat (Season 12)

Best Finish: 2nd (Battle of the Exes & Gauntlet III)

Average Placement: 6.63 (6 excluding DQs)

Elimination Record: 1–5

Diem is an icon for the show and showed a tremendous amount of drive and heart while competing. She also got very close to the win twice once losing the close race up the mountain on Battle of the Exes and once when Big Easy’s collapse cost the veterans team the win on The Gauntlet III. Diem excelled at endurance but she was not particularly great in daily challenges leading to her ending up in the late elimination rounds against strong competitors. Diem also, like Shane, struggled in physical eliminations due to her size and it didn’t help that she frequently ended up against some of the top competitors since socially she was able to make it to the end but then had to face tough competitors like Darrell & Aviv on Fresh Meat, Aneesa on The Duel or Brittini on The Duel 2. She was truly a legend, Rest In Peace Diem.

4.

Tony Raines

Original Show: Real World: Skeletons

First Season: Battle of the Bloodlines

Best Finish: 5 (Vendettas)

Average placement: 7.67 (6.5 excluding DQs)

Elimination Record: 2–4

Tony started his Challenge career not particularly well getting overly involved in hooking up, fighting and drinking but then he had a few really good Challenge performances right before he decided to “retire” from the show. In particular his dominant run on Vendettas showed what Tony could do. He is not the best mentally so puzzles are always going to be an issue and he is fully capable of making a boneheaded mistake that can cost him. Tony has made a big impact in his time on the show and were he to return I would expect him to immediately be a front runner. He has a very strong social game is physically intimidating and willing to make a move and backstab a friend like when he voted in Bananas on Vendettas in order to further his game.

4.

Theresa Jones( Gonzalez)

Original Show: The Challenge: Fresh Meat II

First Season: Fresh Meat II

Best Finish: 2nd (Battle of the Exes II)

Average placement: 5.71

Elimination Record: 2–7

Theresa is someone who improved over the course of her run on the Challenge initially being there more for the party instead of the competition but she started to really come into her own during her later seasons like Free Agents and Battle of the Exes II. Theresa was then also in good shape but had no friends on the show when she came back this past season for Double Agents making it so she got knocked out halfway through. She had some poor luck with partners her challenge career with Jasmine, Ryan and Jay not being the best. Theresa has a bad record in eliminations but ended up going against great competitors with her individual losses against Tori (Hall), Laurel & Kaycee and a win over Camila. Nowadays Theresa looks like she would continue to have a lot of trouble like she did on Double Agents politically but she was a great competitor and one of the best to never win.

3.

Kyle Christie

Original Show: Geordie Shore

First Season: Vendettas

Best Finish: 2nd (Total Madness)

Average placement: 7.67

Elimination Record: 4–4 (1 is technically a DQ against Fessy)

Kyle is better known for being a lot of fun, for his great confessionals, for hooking up and getting into fights but he is a good competitor. He has proven so as early as his first season of Vendettas winning 3 daily challenges and doing well in many others. He also plays a good social game and is willing to make moves to advance his game. Kyle is a pretty good competitor in eliminations but his size does limit him, so for his sake he doesn’t want to end up against a bigger guy in a hall brawl like he did twice. Kyle is also a real threat in finals finishing 3rd on Vendettas beating both Leroy & Tony and coming in 2nd on Total Madness beating Cory & Fessy. Kyle has gotten close and could definitely get off this list and take home a win.

3.

Jenn Grijalva

Original Show: The Real World: Denver

First Season: Inferno III

Best Finish: 2nd (The Island)

Average placement: 3.67

Elimination Record: 5–3

Jenn is the person on this list that has absolutely had the most opportunities to get a win making 4 finals but mostly disappointing in them. She mostly had poor teams in finals with her team on Cutthroat being decimated down to just her and Emily, getting partnered with the mediocre Mandi on Rivals, and having a team of Paula, Ryan & Robin on the Island against the incredible team of Derrick, Evelyn, Kenny & Bananas. Jenn was a good competitor with a winning elimination record and good daily performances but she was a truly excellent political player. It has been a while since Jenn has been on a season and she is not of the same type of physical competitor that we usually see today but that should not take away from the fact that she had a great run and she has by far the best average placement of anybody here and one of the best women to not have a win.

2.

Cory Wharton

Original Show: The Real World: Ex-Plosion

First Season: Rivals 3

Best Finish: 2nd (Battle of the Bloodlines & Double Agents)

Average placement: 7.63

Elimination Record: 7–3

Cory has become a true face of The Challenge and is a big threat to win every season he is on particularly since he has become a lot better politically over the years which a few of his early seasons like Dirty Thirty and Vendettas. He has performed well in a number of finals and definitely shown that he can win. Cory has a great elimination record so it’s a tough task to get him out. The biggest thing slowing Cory is he does not excel with puzzles so in an individual game that will always be a hurdle but I see him as likely to finally get a win particularly if he continues to come on the show as frequently as he has been recently.

2.

KellyAnne Judd

Original Show: The Real World: Sydney

First Season: The Island

Best Finish: 2nd (The Ruins)

Average placement: 4.6

Elimination Record: 5–3

KellyAnne was for a while one of the best women on the Challenge but has only been on 5 seasons of show. She is clearly still in great shape coming in third place on All Stars but that also may signify her not coming back to a regular season again which would be disappointing. She is a great physical competitor nearly upsetting the Champions team on The Ruins with just her and Sarah. She is not the best socially which other people certainly have over her. In eliminations she has a really strong history with a winning record and losing only to strong players like Evelyn, Jenna and Wes & Nany. I would expect her to have the chance to get a win if All Stars continues and she comes back but for now she is one of the best to never win.

1.

Leroy Garrett

Original Show: The Real World: Las Vegas

First Season: Rivals

Best Finish: 2nd (Battle of the Exes II)

Average placement: 7 (5.7 excluding DQs)

Elimination Record: 9–5

Leroy is a Challenge icon and was the reason why I put together this list. He is one of the biggest good guys of the show and had virtually the whole fandom behind him going in to the finals. He does have his flaws which have hurt him in seasons, Leroy is not a great swimmer and also not particularly great at puzzles. However Leroy was one of the best in daily challenges and eliminations particularly in the modern seasons which have undoubtedly been the hardest era of the show. I hope that he is happy moving forward and looks like he has a great thing with his barbershop and a great relationship with Kam. If Leroy were to decide to “unretire” I think he would be finally able to get that win especially since Double Agents just happened and was one of his most successful seasons by far.

1.

Kam Williams

Original Show: Are you the One 5

First Season: Vendettas

Best Finish: 2nd (Double Agents)

Average placement: 5.6

Elimination Record: 7–1

Speaking of Kam, here she is and like her other half, Leroy, Kam is the best competitor of her gender not to win a season of The Challenge. She has never lost an individual elimination and only lost one as a pair. She plays a great political game, is a smart competitor who can be relied on to win puzzles, and is great physically both in eliminations and daily challenges. Every season that she competes on she is a huge threat to win even elevating a rather mediocre partner in Kayleigh on Final Wreckoning to finish in 6th place. Considering we have not heard anything about her calling it quits she is my pick for the favorite to get the win first out of everyone on this list.

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Henry L DiMaria

I blog primarily about The Challenge but occasionally stretch into other reality TV @HenryLDiMaria