Ranking Wes Bergmann’s Worst Decisions on The Challenge

Michael Alvey
6 min readMar 31, 2023

Inspired by episode 5 of The Challenge: World Championship, I decided to put together a list of the worst decisions ever made by Wes Bergmann.

I’ve written a lot about Wes’ strategic game over the years, both good and bad, but today we’re going to be focusing on the ugly. I could have written 5000 words just on that Fresh Meat mohawk, but we’ll just keep it as an honorable mention for today.

Let us remember the worst follies of the “greatest mastermind” in Challenge history.

12. Telling Rogan He Was Going In (War of the Worlds 2)

Jordan and Laurel were able to sniff out that Wes had an alliance with Joss and Rogan by telling Wes they were going to throw in Rogan.

Wes immediately ran to Jogan and told them what was happening, which led to Rogan fessing up to Jordan that Wes gave away the plan, exposing that Wes was working with the UK.

11. Not Telling Anyone He Was Coming (The Ruins)

It was always going to be a tough road for Wes on The Ruins, but he immediately put a target on his back because he told castmembers that he wasn’t going to be on the season.

Wes had been retired at that point and hadn’t been on the previous four seasons, but made the loudest return in Challenge history.

10. Going In Against Bananas (Total Madness)

Wes didn’t know how many more opportunities he had to get his Red Skull, so when Bananas volunteered himself, the stars finally aligned for the longtime rivals to face each other in an elimination (not counting that blind stickfighting crap on Champs vs. Pros).

I think this move was more ego than miscalculation. He was (justifiably) mad that Bananas stole his thunder and put himself in when he knew Wes wanted to go down, but based on the filming schedule he had to have known there were at least a couple more eliminations coming (there ended up being three).

Bananas was obviously better than the other guys left without a skull — Josh, Swaggy, Kyle and Cory.