Being in the middle of the pack is not always the worst thing on The Amazing Race. Being able to keep a steady pace is sometimes all it takes. But then, when a series of bad luck catches up to you, that’s when The Amazing Race really catches up to you. For the lumberjack father-and-son duo, Jeff and Pops Bailey, this race was a challenge to prove that they were always the men they knew they were. But it also brought them even closer. Beyond parent and child. Friends. Jeff knew his father was Superman, and Pops realized his son was his guy. “The fact to be in the race with him, and then to be hanging with him. I learned that, man, this is my guy. Words don’t describe it,” Pops said.
After five solid legs in the race, it was the challenges in Dubai that led to their elimination. Though Pops did fulfill his dream of skydiving in his dream location. When a series of tiny unlucky breaks came their way, including closed door led to their ultimate demise, these two St. Louis natives left the race with their heads held high, proud of what they accomplished on Season 37.
Jeff and Pops Prepared For ‘The Amazine Race’ by Working Together

COLLIDER: The lumberjacks got chopped from The Amazing Race. It’s Pops and Jeff. How are you doing?
POPS BAILEY: We’re doing good. How about yourself?
COLLIDER: I’m doing well. Congratulations on a great run on The Amazing Race. If you could describe your experience in one word, what would it be?
POPS: Man, I would just say love. Out approach was, it was just love, man. It was fun. It was an adventure. Man, I’m with my son. Oh, man, it was just love, man.
JEFF BAILEY: Yeah. I think we both are trying to avoid saying the word amazing, because it’s too cliche, right? It all boils down to the fact that it was amazing. It was solidifying. It was like, we are who we’ve been looking in the mirror and saying that we are, you know what I mean? Like Pops really is Superman. I’m really the son of Superman. So it was reassuring. For the first part of it is, we decided to ignore how impossible it looks to be able to even get on the race. Right? How many 10s of 1000s of teams do they say, sign up?
I don’t care about that. We could easily just submit this video and not get a call back. If we don’t, we’re all right. We’re going to go through this casting process and give it our all, and cancel work for a month, and do all of this, and go all in on possibly doing this. And if it doesn’t happen, it’s going to be devastating, and we’re going to have to realign what we’re doing this spring. But if it does happen, then it’s worth everything. And then it all fell into place, and it happened. So I’m just proud of us for taking that risk, and absolutely paid off.
COLLIDER: What was it like watching yourselves on TV?
POPS: Man, it was incredible. It was incredible. I mean, it was more relaxing because the work was over. We can throw our feet up and watch us do what we did, you know? So it was fun, man.
JEFF: You get to see it from a different perspective. We lived in it, but actually being able to watch and, know, okay, “Wow, this is what it looks like from the outside looking in. That really was that tough. We really did do that.” And you get to see what the other teams were doing when you weren’t there. You know what I mean? We never really pushed ourselves to the front of the pack, so to see them in their struggles, too.
And then what was going on in the back of the pack, what slowed other teams down that didn’t quite get to us. Seeing other teams argue, and it seeing the love between the other teams and how their relationships played out, and thinking “Hey, if I went with a sibling, maybe we’d argue.” I’m glad it was me and Pops because I’m not ever even going to raise my voice in this guy. And it’s out of respect, but it’s also out of love and what our actual dynamic is. It’s more like best friends that are really just this close?
COLLIDER: Going in, what were your expectations? How did you prepare for the race?
JEFF: Well, every day, the best part about it is we cut trees down. So the fact that we’re cutting trees down, we’re getting even more physically prepared every day. It’s what we already do. And we started teaming up on more jobs than what we would typically do, and that was us exercising our skills as a team, as a duo.
So we would be cutting trees down, and typically, if I go up in the bucket, and I’m the one in the air doing the cutting, all the time when I cut chainsaw, I hear Pops, “Jeff, do this. Hey, Jeff, let that limb, put the rope right there, Jeff.” Now that we’re both training for this race, and we’re binge-watching Amazing Race seasons, if you try to yell at me and tell me to do something, I yell out, “Roadblock, Pops, this is a road block. You can’t help me.” I gotta do this my way. We applied the race to our everyday lives and what the challenges that we already take on, and we just did it that way, and that kind of got us prepared to go out and run the race.
POPS: And I love puzzles. I just did a lot more puzzles before we left. Just my memory. Just keep it sharp, yeah. I knew physical we were gonna be great
Between Bali and Dubai, They Loved It All

COLLIDER: You got to see some extraordinary places. Did any stand out as a favorite?
JEFF: Bali was my favorite, man, and the reason I would say Bali was my favorite out of all of them, we got to see the Bali culture the most. When we first landed, it was the middle of the night. It had to have been after midnight, and we leave the airport, and there’s a long drive to that place that we went to in the middle of the night. We had to select a number. It was a very long drive, and the whole entire drive on both sides of the street, you just saw basically a bustling city. You saw markets, and everybody was outside doing stuff, and it’s the middle of the night. You get to see everybody and their community. “I’m coming here to buy this, and I’m coming here to buy that.”
And they’re working together to build little things. That was like a really great experience for me. And we’re racing to this place, so we’re trying to get the cab driver to go faster, but we’re taking it all in, man. And then we got to ride ATVs through the jungle, so we saw the wild side of it, the jungle, and everything. And then we slept in what’s called a homestay where we slept in one of their little huts in that village that we were working in. So, Bali, hands down, man. And then we also saw the beach of Bali when we moved the coconuts around. Everything about Bali was us really being able to take that place in. And I’m pretty sure if we saw more of the other places and was able to really immerse ourselves into those cultures, then it’ll be more competition. But right now for me, it’s Bali. And we were there longer as well because it was two legs there.
POPS: I wanted to do something by the ocean anyway because it was hot. Bali and Dubai was it for me. Because it was water involved.
COLLIDER: For most of the race, you kept a steady pace in the middle of the pack. Was it frustrating not to be at the top, or was being in the middle okay?
JEFF: We are both very competitive. We wanted to win every leg. We never said, “Oh, we’re gonna go out there, and we’re gonna play it low key, and stay in the middle of the pack and not be threats.” We wanted to win every leg. We had certain things slowing us down. Pops’ ankle was in really bad shape for the entire race. That was one thing. And then we never really got lucky in any situation. Luck is a factor in every leg. At some point of the leg. We never found that luck, but we were proud of the fact that we were staying in the race.
We were okay with being in the middle, because we knew every leg that we were giving it everything, and we were excited about the fact that each challenge was something so different, and we were looking forward to these twists that have been talked about. Every time Phil [Keoghan] said there’s a new twist, we got to the pit stop, and he said something about the Driver’s Seat, that’s all we could talk about because we knew that this driver’s seat was going to be an opportunity for these teams that are consistently in the front to make each other mad. So it couldn’t have played out any better the next day when Jonathan and Ana [Towns] ended up making enemies out of other teams in the front. Friendly game enemies.
But that made us so excited when we got to the mat at the end of leg four, and there was five or six teams there because we could stir up some stuff, you know what I mean? And at that moment, we were at that mat for about 10 or 15 minutes with teams just kind of comparing notes. And next thing you know, they have a target on Scott and Lori [Thompson]’s back. And I love Scott and Lori.
Beside Erica and Melinda [Papadeas], that was the other team that was just really close to us. But they were in the front of the pack at this moment, so we were excited to see some tension between those front of the pack teams. And it worked out perfectly, because those teams could have easily banded together and U Turned two teams that were either middle of the pack or in the back. But they didn’t, because that Driver’s Seat and these other twists set everything up so perfectly, and we put in that work socially to make that happen.

Related

“Don’t Tell Me To My Face It’s An Accident Because Then You’re Insulting My Intelligence”: Bernie and Carrigain Break Down the Twist That Cost Them ‘The Amazing Race’

Bernie and Carrigain talk about the highs and lows of their time on ‘The Amazing Race’ Season 37.

Pops Fulfilled His Dream of Skydiving

COLLIDER: Pops, you got to go skydiving. How amazing was that?
POPS: Man, that was something I always wanted to do. And then to do it in the place I always want to go, which was Dubai. And, man, like he said, I always felt like I can do whatever. Do anything. And then I was actually flying. I was Superman.
JEFF: He was flying, man, across Dubai, too. I can’t think of any better aerial view to see.
POPS: Right. Right? That view was just gorgeous, man. I can’t even, words can’t even describe it, man.
JEFF: And it’s funny, because every time I opened up a clue that was a Roadblock, it was the one that said, “Who wants to beat the competition,” I’m in my head, does that mean we skydiving? Even though it doesn’t even sound like skydiving. And I’m thinking, like, man, you give to Pops, because I didn’t want to skydive. I’ll be honest with the world.
Pops, he’s always wanted to do it, and I always screened every Roadblock clue. “This is skydiving, Pops, you do it.”But luckily, I decided to do the drums, and I decided to do the rice, and then when skydiving was out of the way, I was ready to do whatever.
POPS: I was ready to bungee jump. Yeah, that was some Yeah.
COLLIDER: Now let’s talk about the E foil surfing. Looks so fun, but incredibly hard.
JEFF: Yeah, it was. And then, I didn’t have the experience and the knowledge not to wear shoes in the ocean. So I asked the guy. I said, “Hey, should I keep my shoes on?” He’s like, “You can keep them on. You can take them off, whatever.” I’m like, I’m gonna keep them on because it’s gonna give me better grip. So it didn’t give me better grip. It probably gave me more slip. And I got on the surf board, I think I learned it fairly quickly. I was able to do it, I think on my second attempt.
That was so much fun, man. It was very tiring to have to swim back to the surfboard with shoes weighing you down. But, that was my decision to keep those shoes on. He has more experience when it comes to swimming and stuff. So after I got out of the water, he was like, “Man, why did you keep your shoes on?” I was like, “Because?”
POPS: But he got us up front. He got us past Nick and Mike [Fiorito]. Because we was behind them at first.
JEFF: Yeah, passed them up. And I was thinking about the time it would take to take my shoes off, and my socks, and to put them back on and all of that stuff. So I was thinking it makes more sense just leave them alone. Run out there, let’s get this out the way and be done with it.
COLLIDER: It’s two tiny little mistakes in this leg. A fallen pastry and a door closing of a train. How stressful was it knowing those two little things were the reason why the race ended?
JEFF: It’s hard to say that those two things were the absolute reason why it ended. At the time when the piece of, you know, my clumsy self knocked the icing off of the pastry, we were still missing these little white flowers on one of our cupcakes. Every team went through that. Going up there and finding out that they needed to come back.
POPS: They didn’t know that.
JEFF: We had to keep putting our mind to it. What are we missing? What are we missing? What are we missing? So while he’s remaking that other pastry, I figure out that we need those little white flowers. By the time I got the little white flowers on the cupcake, he’s done with the other pastry. I don’t know the correct terms for what kind of pastries these are, but I think they’re cupcakes and a cake. But anyways, we go back and we get approved.
Then with the train, it’s not, we’re not just thinking about missing the train. We’re like, okay, “Give us three more seconds that we could’ve shaved off of here when we’re getting in the cab or when we’re doing this and doing that, then we would have made it on the train.” We’re not sure that in that moment we could have all gotten on that train in the amount of time before that door closed. My biggest regret, honestly, is not just taking both of my hands, grabbing both sides of that door, and finally putting my strength to use.
POPS: I thought about that too.
JEFF: That would be the one moment where everybody could say, like, “Okay, that strength of his.” I could have just yanked both of them, but then we’re in Dubai, and I don’t want everybody to be saying, “Free Jeff.
COLLIDER: Listen, if you were in New York, it’s what everybody does on a daily basis,
JEFF: yanking that thing open.
‘The Amazing Race’ Brought Jeff and Pops Closer

Image via CBS

COLLIDER: What have you learned about yourselves through this journey?
JEFF: About ourselves? That’s a great question, man. I learned some of my weaknesses. I’m a leader type of guy. I lead other people around me in the tree business. I lead my friends that I grew up with. I give them pep talks and tell them what not to worry about and what to stay focused on, things that I’ve learned from my father. But on this race, and my dad has always led me, but you’ll see on the train, I’m still frustrated, right? I’m like, “Man, if we only get on that other train.”
He said, Man, we can’t worry about that right now.” He helped me get my head back in the game. And so I learned that I’m going to be in situations where somebody has to get me back on track, even at this age that I’m in. I learned that my dad is always going to be my dad. We become best friends, but on this race, there were such intense moments where he had to talk to me just the same way as if when I was in middle school getting in trouble.
POPS: I learned that I thought I was always proud of him, but I was so, so proud of him to actually choose me to race with him. And then to show me the love that him and I was..because he kept talking about me a lot. Like, man, this is so cool. And then, the fact to be in the race with him, and then to be hanging with him. I learned that, man, this is my guy. Words don’t describe it.
COLLIDER: It was really beautiful watching the two of you. This past week was the five-year anniversary of when I lost my dad, so it was really special to see the two of you celebrate each other, because I never got to do anything that fun with my dad. But maybe with my mom. We’ll see one day. But my final question, would you do it again?
JEFF: Absolutely.
POPS: Absolutely.
JEFF: Absolutely. No hesitation, nothing holding us back. Pops’ ankle is where it needs to be. After experiencing it, you learn so much from it. The response from the fans of the show and from the supporters of us, our city of St Louis, has been so supportive and positive about it. There’s no way that we would turn it down at any point in life.
POPS: I think it’s a lot of things that me being a little quiet, I held in. I would really speak more now. I would speak a lot more because it just energized us when we do that. And I was trying to hold back certain fun things him and I say and do because that’s our jokes, but it’s been great.
JEFF: And the journey that you guys got to witness between us was more than just geographic. Like Pops at the beginning was so quiet, reserved. Pops has never even had a job interview before. He’s always been an entrepreneur. And just like me, honestly, I don’t think I’ve made a new friend in years. We made 26 new friends out of our racers, our castmates.
So, watching him warm up to the situation, and then by this last episode, he has his bandanna tied around his forehead, and he’s more in it, and he’s like, “I’m gonna beat him in this way.” It was a heck of a journey, if you really watch Pops and how he warmed up to the whole thing along the
way.
COLLIDER: It was so much fun watching you both. Congratulations on an amazing run.
JEFF: Thank you so much.
POPS: Thank you and thanks and enjoy the rest of your day.

The Amazing Race

Release Date

September 5, 2001

Network

CBS

Showrunner

Elise Doganieri, Bertram van Munster, Jonathan Littman