Challenge Total Madness Interview: Wes Bergmann

Hey there, I was lucky to be able to interview Challenge Legend, Wes Bergmann. Wes and I did this interview in late May and talked for over 90 minutes. The reason interview did not come out earlier was: first, it takes a lot of time to transcribe 80 minutes of conversation. Second, during that week, someone I live with tested positive for COVID, which delayed me. Third, by the time I was about to post this article, all the Dee stuff happened. To be respectful to Wes, I didn’t want to post this right after that. However, this interview has thoughtful responses in which Wes talks about his entire Challenge career, play style, the direction of the show, and his opinion of Johnny Bananas. It’s essential to know; this interview was BEFORE his elimination episode on Total Madness.

I edited out all the parts Dee is involved in mostly, and thus the interview picks up in the middle of our conversation. I want to say that before we get into the interview, Wes’s Friends and Benefits Patreon is a project where Wes and friends are doing charitable work for the community and creating consumable content for fans. I did an Extensive Breakdown of it here:

THE INTERVIEW

Q: What was your mindset going into Total Madness after the early loss from the previous season?

Wes: Let’s see here. I’m trying to put myself back in that train of thought. No, I think that season wasn’t as big a blow to my ego as people wanted it to be. I mean, it is what it is. I was sick; I got blindsided, I didn’t have any true friends there. I had just done a really hard, long season, gotten all the way to the end. While other people get to kind of recoup in-between seasons, I just get organized and get back to work. It’s always entrepreneurial season. So I needed a break, and I tip my hat to the four or five people that concocted the plan that got me sent home, but beyond that, it wasn’t much of a bruised ego. I guess there was an opportunity to get those people back and get some revenge, but that doesn’t motivate me much either. I often think it helped me a lot.

If you do well on a season, you tend to get targeted next season. And vice versa of that is also true: if you do bad last season, you tend to have a little bit less of a spotlight on you in the next. Losing early in a big flash of glory definitely made it easier for me to fly a bit under the radar. Even then, I still had to concoct the possum shenanigan, and do as much as I could to stay under the radar. I still had people from the jump coming at me. I love the game, I was in good shape, I had enough time to get in the shape necessary to do well, and I am in love with this game.

Q: That reminds me. When I play Connect 4, the board game, I lose all the time because I try to make Connect 5s on my friends. It’s way more fun to see someone lose on a Connect 5 because their face has so much defeat on it. When you play on the Challenge, I feel like you want to win in a way where people know it. Like, you want to win with style. Do you agree with me?

Wes: Oh yeah. Y’know, a win’s a win. I’m not going to lie like I’m not a competitive guy who loves to win. You’re definitely onto something where this might be a bit botched as an answer, but what I do on the Challenge, and how I play, I consider to be one of my forms of art. Some people pay to watch people fight, and I do what I do, and whether that’s the politics or the shenanigans and all that kind of stuff, I’m always on the creative side of my brain when I do that. Yeah.

It’s not necessarily the absolute best gameplay. The best gameplay is very easy, but it’s boring as fuck. If I wanted to be a really good game player, I’d play like Darrell or Derrick. Respect to them, but those games, the best games you can play are bad television.

I like to do something that is a good compromise between the two. How can I make decisions that are very functional for me in the game while simultaneously not being wallpaper? My job is to go out there and entertain you guys while moving up the ladder in the game. I’m pretty proud of my ability to do that and enjoy it.

Q: The scene in Rivals 2 where you and CT win the Challenge where you’re running up and down the ramp and asking for more balls is one of the all-time Challenge scenes.

Wes: Yeah, that was great. Y’know what’s interesting about that season is that CT has just spent something stupid like 35 days in South Padre and I was there for like two weeks. I was also getting my company off the ground, so I literally had not run around my block, I had not lifted a weight and couldn’t have gone in worse shape. CT could not have gone in worse.

I was honestly planning on going there and have a little bit of fun and do some crazy shit and then bounce and then they paired me with him, and I was like, “Oh god, this is a free win, so I’m gonna take it.” So I kind of leveled with him, and I was like, “Listen, this is a gift that has gotten bestowed to us, and we really would kick ourselves if we don’t fully take advantage of it.”

We formed a plan where we would be very, very disciplined about running in the backyard together. It wasn’t a yard. It was a deck; there wasn’t any grass at all. So you had run circles on that deck, and it was very painful and hot. By the end of it, we were running like ten miles a day in this crazy heat, and we went from horrible shape to really good shape. It all kind of came to a climax at the end when we were sprinting, cross running on that ramp thing, and it was a very serious set of cardio. Then the team that we ultimately lapped in the final was throwing up just trying to complete it. So I’ll be honest with you. If we hadn’t run that entire time, we wouldn’t have won the final. So, I’m proud of how disciplined we were about kind of getting into shape, and it felt like we were copying each other’s math homework before it was due. It was definitely procrastination, but we did it well.

Q: To many people, it’s the most satisfying win in the show’s history.

Wes: Yeah. Yeah, I tip my hat to CT mostly in that I played a great game, I played a very athletic game, I’m definitely a big reason why we won, but he’s the biggest reason that we won. Y’know, they don’t give him enough credit, because it’s not like we ever had to beat someone up, so it’s not like his size ever did anything. What he did that was absolutely magical was he was a freaking political powerhouse. I was a sounding board, but he actually led a lot of that. It was a game where, if I remember correctly, it was very, very important to have allies from the opposite gender because guys would vote for the girls and vice versa. That man has a way with the ladies, so he gets credit for the stuff that he deserves, and I find that there is more credit to be given for the stuff that he doesn’t get enough of the spotlight for.

Q: Love it. Something I’ve always been curious about — so real fans of the show know that Johnny Bananas wasn’t like the main event player for his first seven years of the show. He was on it for a long time and was kind of in the mid-tier of players, and then suddenly he gets thrown into the main event, where you’ve been since the day you debuted. As someone who’s been through everything, what was it like when MTV started putting him next to you in that category, and what’s just your overall relationship with him?

Wes: To start with the first part of your question, him moving up the ladder of importance in the Challenge — have you ever hear of the analogy of the frog that gets dropped into boiling water and immediately jumps out, versus the frog that is put into a pot of water at room temperature and gets slowly boiled to death. He was like the frog that got slowly boiled to death, cause his rise was so gradual that no one noticed it. Not even me. He wasn’t ever like “new to the scene,” he was just, I mean, the first episode dropped in his very first season ever and everyone kind of just forgot it. A very forgettable Real World, and then every season after that, he just got a little further, a little further, and I think a lot of it built the chip on his shoulder and that chip on his shoulder is kind of what made him such a lifer.

When I compare myself to him, at my peak versus his peak, he’s like a little boy, so I never got the hype. Don’t get me wrong; he’s obviously an incredibly important player in the history of the game, and an incredibly important person in the entertainment industry in general. So I don’t want to take too much away from him, but there is a shitload of asterisks on his resume, and he has gotten blessed with a lot of excellent partners. He’s gotten blessed with a lot of good friendships that he cultivated, and the main thing, y’know, there’s luck associated with his friendships sticking around and other people’s friendships, such as let’s say mine. My friendships moved on and got jobs and got married and got kids and all this kind of stuff. He’s a “right place right time,” “capitalize on the opportunity,” kind of guy. And for that, he definitely has my respect.

But peak Wes versus peak Bananas in fucking anything, he’d get demolished.

Q: I’m glad you put the period on that.

[W and Q laugh]

Q: So you said like he’s had friends that he maintained for a long time, some even like a decade. How do you feel about casting in recent years? In recent years, I’ve noticed a lot of older cast members will sometimes complain about the newer cast members, but you’re making friends with seemingly everyone. You’re like, “Oh, Hunter, you’re going to be my number one this season. Devin, you’re my guy this season, etc.” Is casting a problem, or is it other people’s problem for not adapting?

Wes: I definitely think it’s other people’s problem for not adapting. I’m a really, really, really big fan of where MTV is going with who it is that they’re putting on and why. Y’know, I think it boils down to this: Do I want to be reading Allan Aguirre’s recap synopses when I’m a boring old man? There’s no way that I’m going to be able to do the show all that much longer. Who knows?

There is one thing that is remaining constant, and that is, I’m a big fan of the passion that they’ve created for the show and the family they’ve created, and even when I leave, I’m going to keep watching. I want the show to be successful for many, many years, and so because of that, I almost feel like I am more on the side of MTV than I am on the side of the cast members. The cast members see the writing on the wall, and they’re like, “Oh shoot, it’s gonna be twice as hard to get casted now because the pool of people is just so much larger and everyone’s just so much more athletic and so much more proven.” I think that for some of them, it scares them, so they lash out and say some stupid shit. To me, it’s a good thing. I love the international flair; I love the different shows. It just gives them more people to choose from, and so they can bring in different personalities and people that can back up what they’ve said, and I think that Bananas is a prime example of someone that has not done very well at adapting to the newer people. He just, he doesn’t, I don’t know why but he doesn’t make good friends or new friends very fast. I think he could’ve; I think there’s a really good chance that in these last however many years it’s been since he won, that if he adapted a little bit more, he might’ve been able to do better.

You could say the same thing about a couple of other guys. But I’m a big fan of where they’re going, and I like new people. I love playing with new people. They bring a level of passion that I like. Some of the, I don’t know, let’s call them OGs, or people that have done it a handful of times, they sometimes have a tendency to be jaded and don’t want to play the game. Because this is literally my hobby, I go there to play, and that’s it. I’m not there for a job. I’ve got that part of my life taken care of. I want to talk politics all the time. I want to make risky moves. I want to do all the crazy stuff. In my personal experience, the rookies are so much more down to do that type of thing, and I like to play with them more than I like to play with older people. They just wanna, well, some of them, obviously not all of them, but some of them might get to a little bit of a weird complacency, I guess. They’re just not as much fun to play with.

Q: It’s cool looking at your whole career spectrum, of people you’ve aligned with, where it’s like, “Yeah, Wes aligned with Svetlana like 16 years ago, and now he’s aligned with Swaggy C all these years later.” Like, certain people stick to the same people, but you’ll work with anyone.

Wes: Yeah, I will work with anyone. They have to match the strategy, though. I definitely have a filtration system to do my due diligence, if you will. Some of it before the show starts, but most of it in the first couple of weeks, where there are certain things that I look for in people that I want to play with. If those people have those qualities, then I basically give them full trust. I just give in to the relationship, and once they screw it up, then they’re dead to me forever, but a lot of them don’t screw it up.

[There was a portion of this interview where we talked about female competitors, and I’m redacting because of Dee stuff involved, but it segued into a conversation about how the female stars of the Challenge get treated on Social Media, and Wes had a great perspective on everything.]

Q: Hey, no, I get it. I was talking about this with a few friends. I was explaining to them that like, when you think about it, when’s the last time the girl who was like the number one star — who’s in the most confessionals, she’s getting the most screen time — when was the last time she was like, universally like or had a majority of fans on her side? And the second Cara Maria got that role; she got a ton of hate. Laurel’s had a ton of hatred toward her. Even Sarah Rice, who doesn’t even play a villain role at all. She’s a little cocky sometimes, but she’s never even close to a real villain, gets tons of hate. It doesn’t add up. Like, maybe Coral? Coral is probably the last female main star like that, who everyone just loved.

Wes: Yeah, I think that’s accurate. I think that a bunch of fucking super powerful, amazing females that are on our show — that make the show, that produce the show, that star on that show — don’t get the credit they deserve, and I don’t know what to do about it. I can sing it from the rooftops as much as I want, but I don’t know. I don’t get it. I mean, my favorite elimination of the season, quite frankly one of my favorite eliminations of all time, was last week — Jenna vs. Tori.

Jesus Christ, like, let’s talk about how great that episode was. It couldn’t have been closer. It was just; it was almost artistic to watch. And then speaking of artistic, when you really sit back, and sometimes you get caught up in the fact that it’s a game, and you forget, “Oh god, look at the quality of the editing.” Like, how the scenes were cut together and spliced together, I mean, the art behind it. I can’t compliment it enough. It is the best-composed show in the world. It’s debatably the best fucking show in the world. It’s all on a platform where these two women were battling head-to-head in what couldn’t have been a more fair, amazingly constructed game. Like, that game had nothing to do with how much they weigh. That game had nothing to do with some pre-existing skill set that some people are much better at than others because they’ve been doing it their entire lives.

That game was just a true testament of heart and focus, and it went down to the wire with Jenna coming out on top. When I was there, I loved watching every single second of it. I wasn’t enjoying myself just because I liked the women; I was enjoying myself because, shoot, it felt like I was watching the World Cup or the Super Bowl. It was awesome!

I don’t know; I just want to celebrate the female wins a lot more. The show does such a good job of propping them up in the way that they deserve, but the internet just does not digest them the way that they should. I think that kind of stings a little bit.

Q: Alright, as a long-time fan, I need to ask you about Exes 2.

To me, it’s one of the best. It’s just, top to bottom, the entire cast is great. Everyone has good confessionals; there are good challenges and good eliminations. You, Sarah, and Bananas are all just like rolling at your highest level. Do you feel at all like the end game kind of set you up to lose? Because you get a Daily Challenge where teams could literally team-up on you, and then an elimination that was just, “Run down a hallway at Leroy.”

Wes: Yeah. Yeah, uhh, y’know… Yeah, there’s a lot to complain about, I’m not going to lie. But, let’s put it this way: There’s not 1% of me that thinks that that was set up for me to lose. Some of my biggest advocates and all the biggest conspiracy theories disagree with that statement. I’m telling you from the bottom of my heart; it was just dumb luck. Like, bad luck. It was just dumb luck that it all swirled out completely like that. Y’know, that’s just how the cookie crumbles. Now, if there were stuff to complain about, it would be this: In a season based on the foundation of the “ability to get redemption,” why the fuck was I not given some chance to redeem myself.

[Q & W laughs]

Especially when a team broke a rule and was half kicked out but not fully kicked out. But for some reason, they could have very easily, and, shockingly, they didn’t do this, they could have very easily kicked out Nia and Leroy, right? So they could have very easily sent them both home, like numerous times, and then replaced them with Theresa and I. They kind of half did that by putting Theresa in Nia’s place, but why not put me in his place? And then, if I’m correct in saying this, and tell me if my history’s wrong, that would have put me versus Bananas in a pole wrestle event to decide who goes to the finals.

How could that have not been better television? It’s what everybody would have wanted. It would have been the craziest elimination, like, all to decide who goes to the finals. When you look at it that way, I think it was a missed shot, and it sucks for me, but yeah, everyone, including my partner, got a second chance, and I didn’t. I did play a masterful game that season because I learned my lesson on Rivals 2. I was running my ass off in the backyard, getting ready for that final and pushing Theresa to her limits in that backyard that she has never gone to from a long-distance running standpoint, and we were both ready.

We were going to win the entire thing, and it does sting, but y’know, that’s how the cookie crumbles. It makes my wins seem sweeter. I don’t need to win them all. I’m in it for the love of the game. I’m in it for the journey. It stings, of course, but I still look back on that entire season very fondly.

Q: Do you ever regret retiring after the Duel? You took a three-year break, and it was, in my opinion, the easiest era to pick up some wins.

Wes: Yeah. Well, no. I don’t. I’m one of those guys who’s like, a workaholic. I wish I had like nine lives so I could do a bunch of different kinds of jobs. Unfortunately, I only have one life, and I have to pursue the things that take priority. As far as the Challenge was concerned, in that era, there was nothing else I could do. I had already accomplished everything. I know it was short-lived, but I was like, “I’ve won the largest cash prize. I’ve kicked a bunch of butts in eliminations. I’ve taken over crazy storylines and dominated seasons. I was on debatably the most important Real World of its time.” It felt like I came, I saw, and I conquered the shit out of it.

What was next was I needed to finish school, and I needed to start a company. I think it would have been irresponsible not to do that. I didn’t want to get caught up in it, and if you think about it, like yeah, like I could have chopped up a bunch of easy wins, but at the time, no one cared about how many Challenge wins you had. That wasn’t a thing. I know that now, people wanna say things like, “Oh, I’m a three-time champion” or “a two-time champion” or whatever, and I get that’s kind of like a thing now, but it definitely wasn’t a thing back in the day. No one cared. There weren’t enough Challenges; no one knew how long the show would be going… There was no end.

The prize pool back in the day also wasn’t enough. I don’t know if people remember this, but it used to be a $300,000 prize pool, half of it would go to the girls, the other half would most of the time get split up between three, four, or five other dudes, and you’re like, “Shoot. That’s not very much money.” If the prize were a million dollars back then, I probably wouldn’t have gone back to school. I might have eventually, who knows.

I think I popped in and popped out at all of the right times. It made it possible for me to establish my life a little bit and make sure that I got my degree and got a taste of what running a company was like.

Q: Beautiful, just beautiful. I like how you put it too, that people just didn’t care back then. It just really is a good representation, because nobody is treating this show as a grand event.

Wes: No, not at all. Not at all. I look back on those times very fondly, but that’s just not the view that anyone had on it. I definitely wasn’t the first. I don’t know when this all started, but I mean, I trained for the Duel, and that felt so weird. I mean, you looked around, and no one would train, and I’m like, “Hey, you guys, like, how hard is it to do weights and run for a couple of months. Like, it’s not that serious.” You do that; you go on TV, you could win some money. Nobody was there for those reasons. I did those things, and I won. As the prize pool got larger, as there were more incentives outside of the game to do well inside of the game, people started to treat it a little more like a job.

Of all the things to make fun of Bananas for, he is the GOAT at using the Challenge as an infrastructure to build a career. I mean, it’s unparalleled. There’s not a second-place that matches him. He did it with consistency. He did that with training. He took it as a serious job.

He’s just like that guy at a corporation who’s just good enough not to get fired, like that guy still lasts at that corporation a very long time, and eventually he builds up a pension, and that’s what Bananas has done. You have to hand it to him, if he were to put that much effort into building a company, he might be a good CEO one day, but his motivations lie in different places than mine.

Q: What do you recognize as the prime Wes Bergmann season. What do you think was the best version of yourself?

Wes: A season that I think is underrated in terms of its magnificence is War of the Worlds 1. I don’t mean magnificence for me, I mean in general. Like, that cast, that story, that winner, that ending, those alliances, that game, those tribunals — it’s just iconic when it comes to our world. It’s just a thing of beauty, and it’s just so, so good. No, I didn’t win, and yes, that sucked; I would have loved that seven hundred extra thousand dollars that I didn’t get. I got third place; I lost to two very deserving men who were better than me on those days. Well, I should say, better than me on the second day, for the most part. We won’t get into it. I did very, very good on that final nonetheless.

What people sometimes don’t see with me in my early days is that I won a shockingly small amount of daily competitions. Now, in my defense, I had shitty ass partners my entire first decade. It wasn’t until CT that I got blessed with someone who wasn’t 105 pounds. I didn’t have the opportunity to win many dailies, but still, it’s been something that’s eluded me for a very long time, and on War of the Worlds 1, I cleaned house. I did win quite a bit on Exes 2 because I had a good partner, but on War of the Worlds 1, I won a lot of Daily Challenges, which made doing the politics a lot easier. That arms you with the ammunition you need to do those things.

It was a healthy balance between strength and endurance. That’s a mistake I learned the hard way in earlier years, where I would concentrate too heavily on lifting weights, and then I’ve got all this muscle that needs to get carried around in the final. Then other seasons, I came in and only ran and didn’t have any muscle, and obviously, that makes it hard to win in some sort of physical battle.

I’m proud of the type of prep work that I did, which was a phenomenal combination between strength without getting too big, but with enough muscle to push people around if necessary, and also enough endurance to almost beat Theo in an ultra-marathon. Then you add in the political side of things, I mean I took over that season in a lot of capacities. I’m proud of those moments, and those are the parts that I enjoy the most. I’d say that was probably my best game.

Q: God, this is just a dream for me because, like, these are the things I theorize about and try to consider when analyzing the Challenge, and to get such thoughtful responses from you is surreal. Thank you, man.

Wes: May I compliment you back. I’ve read quite a few of your articles, and I think you do a phenomenal job of analysis. If the show was twice as many episodes, I don’t think analysis would be as needed, because they could give more details, but they’re pressed because they don’t want a forty-five episode season cause the viewers would hate it.

That means editing-wise, not every star gets drawn to each other with a perfect line. I think you do a good job of connecting those dots in a very fair way.

Now, that has come back to hit me a couple of times. I’ve seen a couple of things here or there where you haven’t been all perfectly kind to me, but for the most part, I probably deserved most of those hits. You’re well-spoken and well written. I’m a fan of good writing. I don’t want to expose myself as being too much of a nerd, but I study from afar, and you are a very impressive young man.

Q: That means a lot. I’ve worked a lot in the last year or so to genuinely improve the writing of my articles. It’s tough because I’m dyslexic.

Wes: Wow. I would have never seen that coming.

[We small talk back and forth for about another 10 minutes about random stuff and the potential future of Friends and Benefits. However, time has passed, and if you’ve seen social media, people like Paulie, Cara, Brad, Liz, Julia, Hunter, and Nelson have stopped by in Kansas City since.]

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Allan Aguirre

Allan Aguirre

10.6K Followers

26 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.