Last week, we saw Jay take down CT in a 1 on 1 elimination and claim his stake in Challenge history. It was one of the biggest upsets in the show’s history and got me to consider what would be top 10 upsets in Challenge history. Then I wrote it, and now we are here. For this list, CONTEXT matters. Yes, some of these players went on to become top players, but within the context of the elimination, these players faced odds where the heavy underdogs.
Here are some honorable mentions:
Devin v Bananas (Vendettas): At this point, Johnny has too many losses for one to be a gigantic upset.
Hunter v Leroy (Dirty 30): Hunter is a better athlete than Leroy and is a big ball of muscle. It was an upset win, but not huge enough to crack the list.
Dario/Nicole vs Wes/Nany (Rivals 3): Just a weird all-around situation with family involved.
Sarah Greyson Overall (Gauntlet 1): It’s really hard to categorize those early seasons. Her performance was magnificent all season, but there was a lack of history to build off what she was accomplishing.
Onto the list:
10 Jenna beating KellyAnne on Battle of the Bloodlines
Putting this elimination on the list is going to upset some Jenna haters (me included) because this elimination was a bit of a carnival game and a little bit luck-based. Jenna and KellyAnne played in an elimination where players had to spin around and get dizzied, then perform tasks that would be difficult while dizzy (like stacking blocks). The person who completes the three tasks in the shortest amount of time wins, and that was Jenna.
It was a massive win because even though Jenna had won two eliminations already in the season, she had defeated two diminutive rookies (Larissa and Christina). Jenna was facing KellyAnne, someone who other players regarded as a top competitor in her prime. Jenna finally got over the label of quitter from Exes 2 and became the barbie beast.
9 Brad defeating Landon on the Duel 2
As an all-around talent and competitor, Landon is unimpeachably one of the greatest ever to play the game. He is a great swimmer, had cardio for days, can lift massive amounts of weight, and was able to solve puzzles/be the best possible teammate ever. On the final elimination of the Duel 2, Landon and Brad faced off in a game called Back Off. Each competitor has a hook attached to his/her back. Challengers must take the hook off their opponent’s back and place it on a ring (one on each side). The first challenger to successfully hook his/her opponent’s hook to the ring twice wins the challenge.
Landon got a Round 1 DQ for suplexing Brad, and the goal of the elimination was to get the hook, not to wrestle. Landon won Round 2, and then Brad got the massive upset win when at the last minute, Brad tossed Landon’s ring that he was trying to hook to, giving him enough time to steal the win from out of nowhere. Brad pulled out the win, and this was the only blemish on Landon’s immaculate record.
8 Jill & Pete defeating Darrell & Cara on Fresh Meat 2
When you consider the fact that Jill Zoboroski was a former Gauntlet Queen and underrated competitor, it’s not surprising she and Pete were able to win their elimination on Fresh Meat 2 and do so well for the season. However, they were the first to eliminate King Darrell Taylor in elimination. Darrell had was a career 3–0 in eliminations, won 4 straight finals and missed out on the 5th win because he got DQ’d on the Ruins. This time around, Darrell had the #1 overall draft pick (Cara Maria) and should have dominated the season.
Instead, they lost the first elimination of the season because of a lack of puzzle prowess. What’s so crazy in those exiles are essentially mini finals, and Darrell is maybe the greatest final runner in Challenge history. A ridiculous twist that also establishes Jill’s place in Challenge history; and also creates the overall narrative of Cara as an underdog as she was the first boot.
7 Jonna & Jasmine defeating Sarah & Katelynn on Rivals 1
What makes this elimination upset so huge is that the elimination itself was a puzzle. Sarah was very confident that they would crush Jonna and Jasmine, especially if it were Sarah’s forte (puzzles). The duos played in a game where one player is taken away ahead of time and locked in a coffin, buried under a pile of hay. The other partner must dig through the hay to find their partner, and once found, they then solve a puzzle.
Jonna was able to solve the puzzle faster than Sarah, and they lived another day in a game built against them. It was the peak of Jonna and Jasmine’s Challenge career; they never accomplished anything more significant than this, which is a bit sad, but beating Sarah is a huge deal. Sarah Rice is a career 6–2 in elimination. She never lost another elimination after this season, made three finals, won two seasons, and to this day, her only other loss was to Laurel/Kenny. They took down a Challenge legend in their rookie seasons.
6 Nate & Christina defeating Cory & Ashley on Rivals 3
Seeing Cory get embarrassed in something isn’t too shocking of an outcome, but at this point in time, MTV was building Cory up as a significant player. Cory finished 2nd place on his rookie season, and he and Ashley were looking like a formidable pair on Rivals 3. When they faced lay-ups, Nate and Christina, they expected to win with ease. The elimination was one player pushed a giant lever to pull a player hanging on a bar attached to a rope. As they push more, the line extends, and the amount of tension increases. Cory and Ashley figured they would win this elimination with ease because they were much bigger and stronger than Nate and Christina. Unfortunately, they played the elimination with the wrong strategy.
In this type of elimination, the key to holding the bar is relaxing your muscles as much as possible. The tighter you hold, the more the tension cramps your muscles. Sarah Rice gave Christina this insight before the elimination as she played the “O Ring” elimination on the Ruins and almost lost trying to pull too hard. What’s crazy is that when Christina wins Round 1, when she finally releases, she gets shot into the nether, displaying that Cory was actually pushing the turnstile quite a bit.
Nate and Christina never got cast again, while Ashley would go on to become a 2x Champion and is one of the most prominent figures in Challenge history. Meanwhile, Cory continued to fail upwards into multiple seasons and franchises.
5 Derrick defeating Syrus on the Gauntlet 2
Derrick has pulled off a lot of big wins in his Challenge career. However, the one that truly established him as a monster physical competitor was when Derrick took out Syrus in Beach Brawl. A game that was essentially a sumo battle/wrestling hybrid. Derrick took advantage of his ability to get lower than Syrus and had ridiculous in-ring awareness of when to push Syrus out. People see this win from Derrick and think, “oh wow, he can go toe to toe physically with someone much bigger.” From a pure size perspective, Derrick can’t, but he understands the angles and outsmarts Syrus like crazy. Derrick isn’t book-smart, but he has the mind of a fighter/wrestler. Honestly, in another world, if Derrick gets born like 8–10 years later, he probably becomes a pretty good pro-MMA fighter.
If you watch his elimination with Joss 14 years later, Derrick has crazy spacial awareness. In that elimination, a ring out creates a restart; and every time he almost loses, Derrick gets the reset immediately. It’s intuitive to him.
4 Tina and Kenny defeating Theo and Chanda on Fresh Meat 1
Tina and Kenny were considered one of the lay-up teams throughout Fresh Meat 1. They were awful during most of the daily challenges and tended to bicker with one another. In the end-game, Derrick/Diem put Theo/Chanda in to face Darrell/Aviv as they were two huge threats. Darrell and Aviv won the lifesaver challenge, and Derrick/Diem got forced to put in Tina/Kenny (Wes/Casey were bigger lay-ups).
Up to that point in Challenge history, Theo Von was probably a top 5 player in Challenge history, and his partner Chanda had the second-fastest 40 yard dash time of all Fresh Meat prospects. Not the second-best time of all females, but second overall (trailing by less than .1 seconds to Evan). Kenny and Tina were able to create an upset because they were able to solve puzzles and keep pace with the better athletes. On paper, this isn’t a massive upset, but within the context of the times, this was giant. If I had to compare it to a modern-day match-up, it would be like if Jordan and Jenny lost in a mini final to Bear and Nany.
3 Cohutta defeating Wes on the Ruins
On the Ruins, Wes and Cohutta played Spool, a game where players weave a rope through an obstacle course, under and over bamboo poles. The first to weave the entire rope wins. Wes picked Cohutta as his opponent as he did not like that he and KellyAnne still were friends (Wes was dating KA, Cohutta had dated KA in the past). Wes was calling himself a headhunter in confessionals and was way too confident he’d beat Cohutta. Then again, Wes was a career 8–0 in Elimination (he had both the most elimination wins ever, and was undefeated). To this day, no male has won more than eight eliminations other than Wes, over a decade later.
In the elimination, Wes decided to take his time at first and figure out a strategy. Cohutta dove straight in, unspooled the rope with ease, and mid-way through, Wes quickly realized, “Oh shit, I’m losing…oh shit, I probably can’t catch up.” Even mid-elimination, Wes bemoans, “what is happening?” Cohutta created Challenge history and was the first to slay Wes. While Wes has accumulated many losses since then, this was the elimination loss that destroyed his veil of invincibility. It also established Cohutta as a cult hero among Challenge fans. Cohutta winning against Syrus the following week also proved his first win wasn’t a fluke.
2 Jay defeats CT on Total Madness
Is this recency bias? Probably. However, I think when we look back at this elimination over time, all the elements thrown into how this went down will have this rated between 1–4 regardless. For starters, Jay got voted into elimination after already beating Asaf, and was referred to by CT, Jordan, Rogan, and others as the lay-up. CT won the daily challenge to get this opportunity, looked at the elimination itself, and decided, “yeah, I can beat Jay in this.” The elimination was: players have 20 minutes to barricade the entrance to a bunker using provided materials (stones, blocks, chains, ropes). After those 20 minutes are up, players must attempt to break into their opponent’s bunker, fully opening the door. The first player to break into the bunker and switch on the light, wins. When you add in the fact that CT won Knot So Fast a few years earlier against a Challenge legend like Darrell, and now he’s facing the so-called lay-up, it adds another layer to the story. This elimination was physical, mental, and endurance. There were no twists or any chicanery involved. Jay out-strategized and outplayed CT flat out.
Never in Challenge history had someone defeated CT in a clean fashion one on one in anything remotely physical. To some Challenge Fans, God disguises himself as CT, and they watched their God get conquered by the skinny guy from Survivor. From now on, all Challenge fans will look at Jay with a crazy amount of respect. Jay could never win another elimination again, but fans will still regard him highly because of this win.
1 Camila defeats Laurel on Invasion of the Champions
One of the most important aspects of these upsets is that context matters. In 2017, when Camila beat Laurel, the popular opinion of her as a competitor was at an all-time low. After winning Exes 1, she was on a Fresh Meat team that was a mess on Battle of the Seasons. Had an excellent performance on Rivals 2 that got massively underrated because she and Jemmye were never legitimately in contention for winning, and got eliminated on Day 1 of the final. Then she followed it up with Free Agents, Bloodlines, and Rivals 3, and she didn’t make it halfway into any of those seasons and was more known for drama. Add in the fact that MTV had replayed her falling in the pool and yelling “YOU’RE GONNA DIE” a million times; it made Camila seem like just a crazy person (which she was). Like fans were beginning to forget she was a great player because her actions did not reflect an elite player.
In the final elimination of Invasion, Camila had to face Laurel in Knot So Fast. Camila was a career 6–4 in eliminations, meaning if she lost that elimination, she’d be 6–5 overall for her career, and only two finals appearances in 9 seasons. A good record, but not elite. Laurel was undefeated for her career with a 9–0 record in eliminations, a record that will probably never get touched. What was crazy about Laurel’s record is she had HIGH-QUALITY wins (2 wins over Theresa, 2 over Cara, 1 over Sarah, 1 over Aneesa). Laurel had just devoured Cara in elimination while Cara was in her absolute prime and was hungry to prove to Laurel she was as good/better than her. Not only that, but Laurel owned two elimination wins over Camila!
During the eliminations first round, Laurel was creating intricate loops and had a much easier time carrying the giant ropes. In the end, Camila’s amazing cardio won her the elimination as Laurel tired out. Camila was the first to defeat the giant (only to do it clean), and she completely redefined her career as a competitor. Camila would become 7–4 in eliminations and 3x Finalist, and her following season, she’d win two more eliminations to grow to 9–4, a 4x Finalist, and 2x Champion. What really sucks about all of this is Camila chose to be racist, toxic, and an overall crap person while accomplishing these great feats. Sometimes the bad guys win, and we have to deal with it.