10 of the Biggest Epics Fails in Challenge History

Allan Aguirre
10 min readSep 17, 2019

Wes losing to Bear after getting voted in by Josh on War of the Worlds 2 was a pretty big flop for a challenger who views himself as one of the greatest. However, it was not one of the 10 biggest fails in Challenge history and definitely not even in Wes’s top 3. In Challenge history, there have been many epic fails/flops, and I decided to rank 10 of them. With this list, there are going to be a ton of moments that got left off. I AM SORRY IF YOUR FAVORITE MOMENT IS LEFT OFF. If you have one, please leave it in the comments of wherever you found this article. There have been so many epic fails that we deserve to commemorate them all!

Also, what I define as a Fail/Flop are moments that either could have been easily avoided or were moments when people who were expected to succeed lost. The Bananas backpack is not a failure because everyone expected CT to beat him. Was it still hilarious? Yes.

#10 Nany and Theresa burn Leroy on Rivals 2

Leroy and Ty had a great situation on Rivals 2 as Leroy was a house favorite who had not gotten voted into elimination during his first two seasons. That is until Nany and Theresa decided to burn a vote on their best friend and sexual partner instead of taking a shot at any other team to possibly put a target on themselves. Unfortunately, there were only six total votes among the female teams, and a third of them got burned onto Leroy. Diem used this to her advantage and voted Leroy and Ty, a circumstance she never saw possible until two burn votes occurred.

Nany and Theresa’s teams were in the minority of the game at this point, yet they threw the one male team which was entirely on their side(s) into elimination. That is a top tier political game.

#9 Derek can’t climb a wall on the Duel 2

If you don’t remember Derek Mccray, I do not blame you. He came from Road Rules Viewers Revenge and then appeared on Gauntlet 3 and the Duel 2. Derek was well-respected among his fellow cast members as he was a fit guy with and a college athlete. The rookie team on G3 referred to him as their strongest male on multiple occasions.

When Derek was on the Duel 2, he decided to call his shot by going against Evan in elimination. Unfortunately for Derek, he couldn’t climb a wall. This man who viewed himself as a top competitor would have lost to almost anyone because he couldn’t even get started.

#8 Jodi calls out Veronica on Inferno 2

On the Inferno 2, Jodi got thrown into elimination by the Bad Ass team and went against her team’s own decision to vote Tonya into elimination by switching the vote herself and going after Veronica. This move angered both sides and would have been iconic had Jodi been able to beat Veronica.

Unfortunately, she did not account for Veronica being a velcro master. Jodi made a move which only made her enemies and resulted with egg on her face. It’s crazy how epic of a failure Jodi had considering she would go on to win her next two Challenge appearances and dominated the Duel 1. Ultimately, we will remember Jodi’s Challenge career fondly, but she started it awfully.

#7 Wes’s Final Performance on Rivals 1

We watched Wes describe himself as a Greek God who was bigger, stronger, faster, and smarter than all his fellow Challengers. When he made it to the final for Rivals 1, he completely crumbled under pressure and struggled with almost every part after the initial kayak. Wes was dehydrated as he did not drink enough water beforehand (dumb). He was no help during the puzzles, struggled to eat his food, and needed Kenny to stand on the rock for almost the entire night portion. Yes, Wes and Kenny had a significant lead on day one, but Tyler was advised not to compete beforehand due to illness. In the end, Wes could not keep up with Kenny in a final at all.

Watching someone who viewed themselves a God be humbled is an incredible experience. It helped Wes in the long-run as he performed much better as an individual during the War of the Worlds Final eight to nine years later. Wes’s most idiotic moment from this final is when he decides to put some of the boulder they were carrying in his socks. He was tearing up the skin on his ankles and putting more weight on his legs.

#6 Tonya and Tina sink the Bad Asses on Inferno 2

Tonya was actually a solid competitor between Inferno 2 and Inferno 3. She was fit, agile, and competent in some of the weirdest challenges. However, on Inferno 2, she stroked her own name as a competitor a little too much. While she proved herself in the Inferno by winning two eliminations, she stumbled in the Final as she got incredibly drunk the night before the Final. That’s the opposite of what you should be doing before a Final, especially after hyping yourself up by saying you run ten miles as a workout

Tina also did just as poorly as Tonya in this final, which is depressing considering she did not get drunk with Tonya. It sucked watching an amazing “Bad Asses” team, which consisted of Abram, CT, Derrick, Veronica, and Rachel lose due to two weak links. Then again, the Good Guys teams did consist of three Hall of Famers in the Miz, Landon, and Darrell, along with TV and Film’s own Jamie Chung. Maybe trimming the Good Guys “fat” too much made them incapable of winning regardless, yet it would have been a better final with a closer finish.

#5 Nelson slapping Derrick on Dirty 30 and Tina punching Beth on the Duel 1

Following Invasion of the Champions, Nelson faced a stacked deck as he and his “Young Bucks” attempted to take on the entire house. He was forced to eliminate his best friend Hunter and was fighting every week to win (he was killing some of the challenges). Nelson’s dream had come true as he had become a somewhat star of the show as it was him vs. the house and he was putting up a fight.

Considering Hunter had won Redemption and then the next daily challenge, he and Nelson were in good shape to make a decent comeback. Then Hunter popped off on Kailah and put a target on himself and Nelson. And eventually, this resulted in a drunken Nelson arguing with Derrick and connecting on a very weak slap to Derrick’s face. Nelson was sent home for fighting, and it’s incredibly disappointing considering that it was such a soft hit. Yes, he got some decent shoves in, but the slap/hit on Derrick’s face was not much. Like if you’re going to get eliminated, make it big. In the end, Nelson looked like a bitch because it was a small hit. I love Nelson, but he regrets that moment.

For the same reason, I list Tina’s dismissal from the Duel 1. Tina was coming off a second-place finish and couldn’t even land the punch that got her disqualified.

#4 Paulie’s Purging on War of the Worlds

If you watched the Challenge War of the Worlds, you’d have known that Paulie was a major figure. Similar to Wes on Rivals 1, Paulie put himself on a pedestal. In Paulie’s mind, everyone was playing for second place.

Then the final purge happened. An event which involved speed, balance, and climbing, all things that Paulie is good at. What happened? Well, he failed on his first attempt and possibly concussed himself. Then he fell a second time and his body hitting the freezing water sent him to shock (if it wasn’t already).

A single snag in the road led to Paulie getting eliminated. He even said before going that he would be setting the number one time.
Paulie knows how to make himself not sympathetic whatsoever.

#3 Tony picks Shane for elimination on Invasion

During Invasion of the Champions, Tony saw himself as the new king of the Challenge with Bananas, CT, and others, not in the fray. When they finally arrived, he viewed himself as king of the underdogs at least. Sadly, he and his alliance did not hold total power in the game, and he ended up in elimination as Ashley voted him in. However, his alliance was able to control the house vote for which male he would see in elimination. They picked Shane because Tony believed that Shane was the weakest player left.

In a game of Tuk Tuk Bang Bang, Shane figured out from watching Sylvia and Kailah that the best way to attack the elimination was by staying low and hitting the Tuk Tuk in the center where the weight of the Tuk Tuk would lean forward. Meanwhile, Tony decided to hit the top of the structure super hard, which in actuality creates a recoil and would move the Tuk Tuk both forward and backward.

#2 Cory loses to Nate on Rivals 3

Cory went on a steam-roll to start his Challenge career. He set a record for the most consecutive daily challenge wins ever and then finished second place alongside his cousin. He excelled the following season with Ashley as his partner, and they were viewed as the strongest team outside of the Bananas Axis by Bananas and Sarah.

He had deals with Bananas, Wes, and Dario. He and Ashley were killing it in the challenges. Then it all blew up because Nicole talked to her cousin Nany and they began to poke holes in his game. Cory and Ashley got thrown into the jungle, and even though they had to face Nate and Christina, we assumed they would walk away with an easy win.

Instead, Cory and Ashley got torched by Nate and Christina. If you don’t remember Nate, he was the guy who refused to jump out of an airplane, the guy who cried a ton of AYTO, the guy who got punked on AYTO by Brandon the quitter, and the guy who was generally awful at the Challenge. Cory was the future face of the franchise, and he lost to Nate. It’s a bit hypocritical to not include Ashley’s failure as well. However, Christina LeBlanc is surprisingly competent in the daily challenges if you watch closely.

#1 The Zach Nichols section

When I was first brainstorming this article, there were four significant Zach moments which immediately came to mind. It felt weird putting him on the list only once and multiple times. In the end, my decision is to give him the #1 spot with his biggest flop moments. In all honesty, Zach is a fantastic challenger 80% of the time, but the 20% that’s not, is genuinely epic failures. Zach is the epitome of the phrase “the bigger they are, the harder they fall”.

#1 Cheats during his Rivals 2 Elimination
On Rivals 2, Zach had a total meltdown and eventually found himself in elimination due to he and Trey finishing last in the daily challenge. Zach chose to cheat in a game where players had to break through four doors, in which Zach broke three of them when each partner had to do two. What’s funny about this failure is Zach broke the easiest floor. He saved himself and Trey a maximum of two seconds by cheating. It was even funnier considering Zach threw his helmet into the crowd after winning to flex.

#2 His entire Free Agents Final
Zach’s Free Agent run until the Final is one of the most underrated in Challenge history. On average he was the highest picked player for daily challenges and never once was considered a target to get voted into elimination. Zach coasted through to the final and had an excellent shot at winning on paper. Except for the fact that he’s not a great kayaker, was not built for high altitude endurance running, and the fact he struggles with communication. Zach was so bad that he almost cost a Laurel an entire hour lead she had on Nany.

#3 Losing his Exes 2 elimination to Jordan
Zach was a huge man with long hair. He looked like Thor. In an elimination where players had to swing a hammer, he got outperformed by a one-handed man. To make matters worse, Jonna outperformed Sarah; this is after Zach had berated her all season as a partner.

#4 Getting himself and Amanda thrown into elimination on Final Reckoning
On Final Reckoning, Zach and Amanda were dominating the daily challenges. Despite his distaste for Amanda, her ability in mental competitions while also being able to carry her weight physically made them a match made in heaven (or maybe hell). After winning a daily challenge, Amanda wanted her and Zach to vote for Tony and Bananas, while Zach wanted to vote for Hunter and Ashley. Neither player wanted to betray their friends, and this led to Zach agreeing to just throw themselves into elimination “to make a point.” In the end, Zach and Amanda lost, and Zach broke his nose. Zach made a point for sure.



Allan Aguirre

27 years old. I blog about MTV's the Challenge and will dabble into other subjects occasionally. Follow me on Twitter for the occasional bad joke.