CHAPTER 381 Ft. Bobby Regan
Gypsy Tales
Jase Macalpine
4.6 • 564 Ratings
🗓️ 29 January 2026
⏱️ 115 minutes
🧾️ Download transcript
Summary
Bobby Regan joins us for Chapter 381. Bobby has taken Star Racing Yamaha from a small privateer operation to the most dominant team in the sport over the last decade, leading riders like Cooper Webb, Haiden Deegan, and Eli Tomac to championships. Bobby shares his story from his younger years to where the team is today, opens up about how gambling helped fund the early days of Star Racing Yamaha, and breaks down the team dynamics and tactics he used to get the most out of his riders—including pinning Cooper Webb and Jeremy Martin against each other. He also explains why he was so committed to Cooper Webb, what he saw in him early on, and even shares what Haiden Deegan is really like as both an athlete and a person.
Gypsy Gang, as always, thanks for listening. Drop a comment, like, and subscribe!
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00:00:00 Intro
00:01:30 Welcome Bobby Regan to The Podcast
00:02:57 A Brief Background on Bobby
00:08:37 Dixxon Flannel Ad
00:09:28 Rewinding to the Start of Bobbys Career
00:16:50 How Star Racing Yamaha Began
00:20:43 The Stewart Family
00:22:34 How Star Racing Became a Winning Team
00:35:20 Aura Frames Ad
00:36:36 Gambling Stories
00:41:24 Bobby's Secret to Success
00:48:28 Buying the Goat Farm and Becoming Dominant
00:57:07 Star Racing Yamaha's First Champion! Jessica Patterson
01:01:42 Men go to Mars Ad
01:03:21 Star Racings First Pro Motocross Championship
01:13:20 What Cooper Webb's 2025 Supercross Championship Meant
01:17:44 Losing Chase Sexton to Geico Honda
01:21:20 Eli Tomac
01:22:37 What is Haiden Deegan Really like!?
01:26:21 Untold Haiden Deegan Story
01:27:26 Why Riders Leave the Program
01:30:12 Star Racing's Next Champion
01:32:19 Fist Handwear Ad
01:33:45 Star Racings Biggest Rule
01:39:00 Cole Davies Whoop Speed
01:40:59 Millsaps Training Facility
01:42:20 Best Rookie Season Ever!?
01:46:44 Australias Next Champion!? Blake Bohannon
01:48:51 What you Need to Know about Bobby Regan
01:54:01 Haiden Deegan is like a Son to Bobby
01:54:44 Outro
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Transcript
Click on a timestamp to play from that location
| 0:00.0 | For a performance, Eli Tomas, back-to-back wins to start 2023. |
| 0:05.8 | Behind the most dominant team in motocross is a good old boy from Mississippi who loves to win. |
| 0:11.2 | The winning part is what I had always done. |
| 0:14.2 | Bobby Reagan isn't interested in participation trophy. |
| 0:17.8 | He's interested in results. |
| 0:20.8 | He took Star Racing Yamaha from a team just lining up on the gate to a full-blown dynasty, |
| 0:27.2 | winning over 40% of the sports championships in the last decade. |
| 0:31.7 | Today, when riders walked into Star Racing, the expectation is simple, win. |
| 0:36.6 | You guys go from a team that people didn't want |
| 0:39.0 | to ride for and nobody took seriously to a team where when you go there, you got to win. So what's |
| 0:44.6 | Bobby's secret? He loves competition. There's almost nothing Bobby Reagan won't do to win. And when |
| 0:50.7 | you have a team owner who bets on himself literally it gives writers the kind of confidence |
| 0:56.1 | that you can't coach my wife i was gone a lot and she'd like to go to the casinos she supported the team |
| 1:03.1 | for the first five years on her winnings bobby doesn't just build winners he stokes the fire |
| 1:09.0 | and sometimes he's not afraid to like |
| 1:11.3 | to match himself. |
| 1:12.3 | I told Cooper, I said, don't put up with any shit from that French guy. |
| 1:16.0 | And I want you to go up to his ass before the Damoto starts and tell the motherfucker. |
| 1:20.6 | Gypsy gang, welcome Bobby Reagan to the podcast. |
| 1:32.3 | Test him, testing one, two, one, two. You ready over there? |
| 1:34.3 | I'm ready. |
| 1:34.8 | You're the base guy? |
... |
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