The Challenge 41 will be Aneesa’s 20th season on the show, and she still hasn’t secured a win. If she manages to win this season, she’ll have the longest climb to obtain a victory in the Challenge’s history — but let’s be honest, the odds aren’t in her favor.
Aneesa is not alone in this overdue club; there are quite a few Challengers who have 10+ appearances and haven’t won. At this point in Challenge history, dozens of people have surpassed the 10 season threshold, but no one has won their first season after their 10th appearance.
This seems like a curse — a conspiracy theory I’ve dubbed the Illumaneesa, affectionately named after Aneesa. The idea is simple: If a Challenger hasn’t won by their 10th season, the win is never going to happen.
Why 10 seasons?
In 2013, CT won Rivals 2. It was his ninth season, and it had taken him nearly a decade to secure his first win (The Inferno filmed in late 2003 and Rivals 2 filmed in mid 2013). This made him the Challenger with the most losing appearances on the show before getting his first victory. At the time, CT was one of the first people to accumulate nine Challenge appearances on his resume.
Since 2013, substantially more people have accumulated double-digit Challenge appearances. Aneesa was the first player to amass 10 Challenge appearances without a win, a milestone she hit on Free Agents. She has continued to appear on the show, but despite her numerous attempts to win, she’s never won the grand prize.
People may criticize Aneesa’s athletic abilities, but she’s not the only person to surpass nine seasons without a win. Some of the people in this club had seasons where they appeared to be front-runners, but it only seems like their struggles are getting worse with each passing Challenge appearance.
Who’s in the 10+ losers club?
These people have appeared on 10 Challenge seasons or more and have never secured a first-place finish.
Note: I am including appearances on the flagship show, All Stars, the Challenge USA, and the World Championship. I will also include appearances on All Stars Rivals and Challenge 41 in the tallies, but I will not consider unaired outcomes.
- Aneesa: 20*
- Leroy: 16*
- Nany: 14*
- Cory: 11
- Beth: 10
- Nelson: 10
*indicates the person has unaired results on All Stars Rivals or Challenge 41
While the roster is fairly short at the moment, many people are close to joining the 10th club, including people who are very active in the Challenge/ All Stars scene.
- Jemmye: 9
- Kellyanne: 9
- Robin: 9
- Tina: 9
- Amanda: 8
- Jenna: 8
- Josh: 8
- Ryan: 8
- Shane: 8*
- Tony: 8
Can the curse be broken?
Obviously, no one is doomed to never win The Challenge, and I anticipate the curse will be broken eventually — some of the people on this list are among the best to never win. However, accumulating 10+ Challenge appearances without a win indicates that competitors have really bad strategies on the show and they need to change something.
In terms of Challenge appearances, CT had the most before he got his first win. However, if we used time to measure the length between debut and first win, it took Jonna over a decade. When she returned for All Stars 2, it was about 10.5 years after she debuted on Rivals. Her long hiatus between Exes 2 and All Stars allowed her to refine her strategy, and this proved to benefit her game.
Competitors like Aneesa, Leroy, or Nany use the same strategies season-after-season. They seem afraid to make power moves, and the strong competitors they protect always beat them in the end.
Let’s be honest — the likelihood of Aneesa winning is really low, but it would be a huge (and pleasant) surprise if she pulled off a win. Challenge fans would be shocked, but until that moment comes, the continued failures are getting really boring to watch.
Stop Being Polite 