The Top Ten Jordan Wisely Challenge Moments

Henry L DiMaria
8 min readJan 25, 2023

Jordan is widely considered one of the greatest competitors we have ever seen in Challenge history. He is a three-time champion with a 10–4 elimination record and has $833,000 in winnings. He had yet another great performance this past episode both with him and Aneesa winning against Kaycee & Kenny in ‘Knot so Fast’ and then beating the significantly bigger Chauncey in the, (partially strength-based,) ‘Rumble Tumble’ elimination. Jordan once again showed that he is not only an exceptional athlete but also has a remarkable ability to use strategic thinking in eliminations and dailies to overcome his size disadvantages and his physical disability, (which he never uses either as an excuse if he does lose). Even though it was an impressive feat, I don’t even think Jordan besting Chauncey is that high up in his top Challenge moments.

In terms of top moments, I am taking into account everything including challenge wins, elimination performances, fights & drama, final performances, and more.

Honorable Mentions:

Beating Shane in Crazy 8 as a mercenary on Vendettas

Beating Theo in Under the Hammer on War of the Worlds 2

Beating Leroy & Ty in Last Chance as a rookie on Rivals 2 (alongside Marlon)

Defeating Kaycee & Kenny in Knot So Fast with Aneesa as a partner

10. Beating Chauncey in Rumble Tumble

Jordan has over and over again shown that he is somebody who should never be counted out. He has won strength games against bigger guys and grip challenges against competitors with two hands even though he has just one. He always seems to know exactly what to do to make it hardest for his opponent and easiest for him. I praised Chauncey for beating Jordan in the Last Life daily but Jordan has now gotten him back, this time sending Chauncey home. Jordan explained it fantastically in the episode himself; He went to the side instead of straight ahead to catch Chauncey off balance, he let Chauncey score a point which also took them closer to his next stack, and finally dug into the ground to tire Chauncey out so he could be the one to finish the job. The only reason this is not higher is that Chauncey was a rookie this season and we have seen Jordan’s incredible ability to approach competitions for some time now so a little bit of the novelty has worn off.

9. Betraying Bananas & Nany by sending them into the last elimination on Battle of the Exes 2

You often have to make cutthroat moves in order to win a game like The Challenge and in this case Jordan certainly did. He and his teammate Sarah made the cold-blooded move to betray allies Bananas & Nany, sending them in against Leroy & Nia in the final elimination. He betrayed their alliance to further his own game which was the right move even if his partner Sarah did have to talk him to it. This moment definitely belongs more to Sarah than Jordan, but he was still a big part of it. This was one of the most consequential moments in Challenge history as it directly lead to not only Jordan & Sarah winning but also everything that happened between Sarah & Bananas since then including the infamous Rivals III finale.

8. Winning War of the Worlds 2 as part of Team UK

For most competitors winning a season is the top of the mountain in terms of accomplishments. But Jordan is not like most competitors. He was one of the dominant players of War of the Worlds 2 and along with Tori was the major opposition to CaraMaria and her Cara’s Cult alliance. The reason that I have this challenge victory so low is that he won it as part of a team that included three other great competitors, (Dee, Rogan & CT). Team wins are generally considered less impressive than winning as an individual or in pairs since you have several teammates to potentially lean on. Plus, in teams, it is usually a matter of winning or losing instead of competing against multiple opponents. A final factor making this victory less notable across Jordan’s career is that their team had the benefit of a big lead when Paulie collapsed and slowed down Team US.

7. Beating Zach in Hammer it Home on Battle of the Exes 2

Since this was a pairs elimination, Sarah defeating Jonna played a big role in ‘Hammer it Home’. It looked like Jordan winning his round was going to be an uphill battle. He was sent into elimination against the much bigger & two-handed Challenge Champion Zach in a hammer-swinging competition. Jordan showed for the first time his ability to think quickly by focusing on proper form overcoming both Zach’s strength advantage and his disadvantage that he was not able to use both hands in the same way.

6. His proposal to Tori Deal on War of the Worlds 2

If you are reading this I assume that you are aware of how the Tori & Jordan relationship has played out from here, particularly since it has been such a major focus of this season. Regardless, this moment was a big deal for the show since Jordan and Tori were pretty much the Challenge ‘It Couple’ for several years. His proposal is one of the most rewatched noncompetition moments of the recent Challenge and one of the moments I most associate with him.

5. Beating Darrell in the Steamroller elimination on All Stars 3

As I discussed when Jordan beat Chauncey in this past elimination and when he beat Zach on Battle of the Exes 2, Jordan has repeatedly shown himself able to overcome massive disadvantages. On All Stars 3, Jordan did the same yet again, in this case, he went into a strength and endurance-based elimination against four-time champion Darrell, (who was also coming off finishing as runner-up in both previous All Stars seasons). Jordan was on the ropes and right on the precipice of losing due to Darrell’s strength. Instead of continuing to push against him, Jordan positioned his body to act as a dead weight and used that strategy while talking shit to wear Darrell’s body down. After nearly an hour Darrell’s body gave out and Jordan proved yet again why he is one of the best by beating a Challenge legend in an elimination while being at a disadvantage.

4. Winning Battle of the Exes II (with Sarah Rice)

Jordan had several good moments in his first two seasons and has physically shown himself to be a great competitor and a great character on the show. However, if a competitor really wants to become a Challenge legend, winning is the easiest way to get there. On Battle of the Exes II, Jordan let Sarah take the reigns strategically and they worked well together as a team, winning three daily challenges and the aforementioned elimination round against Zach & Jonna. They eliminated two of their biggest competitions, (Wes & Theresa and Bananas & Nany,) by sending them in the last two eliminations. Jordan physically killed the final with the help of a great partner Sarah. They lead the whole way through and Jordan took home his first championship beating a strong team in Leroy & Theresa.

3. Flipping all of the Kill Cards to face Bananas in the Wrecking Wall elimination on Free Agents

The Challenge is a show where you often need to make bold moves in order to win the game and Jordan made one of the boldest moves in the history of the show. He flipped all of the “kill cards” to ensure he would go into the Wrecking Wall elimination and try to take out Johnny Bananas. Some call it the cockiest moment in Challenge history and some argue it was one of the dumbest decisions, but what it definitely was, was a jaw dropping moment. Seeing Jordan defy playing the typical follower game by not backing down to the veterans wishes was amazing, especially since he was going up against the (at that time) four-time champion and top dog even after seeing he would be at a disadvantage in the elimination due to his hand. This moment was iconic and one of the moments that gave a glimpse of Jordan’s future in The Challenge, where he is widely regarded as one of the best of all time.

2. Beating Josh in the End of the Rope elimination on War of the Worlds 2

A one-handed man winning a tug of war sounds more like the setup to a sort of distasteful joke and not an actual thing that happened in a challenge elimination. Josh is certainly not the most impressive opponent that Jordan has beaten in an elimination round, but this elimination is the one in which he overcame the biggest disadvantage. Jordan was able to recognize that if he tried to win by the conventional methods of just trying to overpower and out-pull Josh he would have no chance. So he watched Josh and by strategically attacking him he turned it into a balance and mind game. Jordan varied how much resistance he was giving and used his superb balance and body control to win even though he could not hold onto the rope as well, he had less pure strength and was near the end of his rope in both rounds. This was a masterclass by Jordan on how to overcome and by using his brain to win an elimination he never should have.

  1. Winning the Dirty 30 Final on an Injured Leg After Skydiving to Start the Final

Winning an individual challenge season is by my account one of the most impressive feats you can do on The Challenge, and on Dirty 30 Jordan did that but also much more. Not only did he win an individual challenge, but he also won one of the most grueling finals over two multi-time champions, (and consensus top ten competitors in the show's history). To top it all off Jordan did all of this with a hairline fracture in his leg which he received when his parachute malfunctioned and sent him crashing into the ground way harder than it was supposed to. In my opinion, this win is Jordan’s greatest moment on The Challenge.



Henry L DiMaria

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