“I was superman” —The Amazing Race star Pops Bailey talks about skydiving for the first time during the competition 

For lumberjack duo Jeff and Pops Bailey, The Amazing Race Season 37 offered more than just a competition—it became a journey of father-son bonding and personal discovery. After five solid legs, their adventure came to an end in Dubai, but not before Pops fulfilled his lifelong dream of skydiving.

"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," Pops shared with enthusiasm.

Declaring further:

"And, man, like he said, I always felt like I can do whatever. Do anything. And then I was actually flying. I was Superman."

The breathtaking aerial views of Dubai's spectacular landscape provided the perfect backdrop for this bucket-list moment, creating memories that transcended the competition itself. Despite their elimination following a series of unfortunate setbacks, the St. Louis natives left with pride in their accomplishments and a deeper connection with each other.

The Amazing Race’s Jeff and Pops Bailey got to go skydiving in Dubai

When the opportunity to skydive presented itself during a Roadblock challenge on The Amazing Race, there was no question who would take it on. Jeff immediately knew this was his father's moment:

"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?" Jeff admitted.

He elaborated, point-blank:

"I'll be honest with the world—I didn't want to skydive."

For Pops, however, the experience was nothing short of magical. Words failed him when trying to describe the panoramic view of Dubai from thousands of feet above.

"That view was just gorgeous, man. I can't even, words can't even describe it," he reflected.

Their journey across multiple countries on The Amazing Race showcased the duo's resilience and adaptability. Bali stood out as a highlight for Jeff, who appreciated experiencing the local culture deeply.

"We got to see the Bali culture the most," Jeff explained.

Declaring:

"The whole entire drive on both sides of the street, you just saw basically a bustling city... That was like a really great experience for me."

The team also tackled challenging physical feats, including E-foil surfing, an experience Jeff described as "so much fun" despite being "very tiring."

A bonding experience for the father-son duo

Beyond the competition aspects, The Amazing Race served as a powerful bonding experience for the father and son. When asked what he learned during this adventure, Pops' answer was simple but profound:

"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," Pops shared.

Explaining:

"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."

Jeff similarly discovered new dimensions to their relationship, noting how his father's guidance remained invaluable even as adults facing extreme pressure.

"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."

Though their The Amazing Race journey ended before the finish line, the Baileys' experience exemplified the show's power to transform relationships. For them, the race wasn't just about competition, it was about love, as Pops so aptly summarized when asked to describe their experience in one word.

"Man, I would just say love. Our approach was, it was just love, man. It was fun. It was an adventure."

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The Amazing Race Season 37 airs Wednesdays at 9 p.m. ET/PT on CBS and is available to stream on Paramount+ and Hulu.