GYPSY TALES

Chapter 381

Bobby Regan

29 Jan 2026 · 1h 55m

With Bobby Regan

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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!

Chapters 31

  1. 0:00Intro
  2. 1:30Welcome Bobby Regan to The Podcast
  3. 2:57A Brief Background on Bobby
  4. 8:37Dixxon Flannel Ad
  5. 9:28Rewinding to the Start of Bobbys Career
  6. 16:50How Star Racing Yamaha Began
  7. 20:43The Stewart Family
  8. 22:34How Star Racing Became a Winning Team
  9. 35:20Aura Frames Ad
  10. 36:36Gambling Stories
  11. 41:24Bobby's Secret to Success
  12. 48:28Buying the Goat Farm and Becoming Dominant
  13. 57:07Star Racing Yamaha's First Champion! Jessica Patterson
  14. 1:01:42Men go to Mars Ad
  15. 1:03:21Star Racings First Pro Motocross Championship
  16. 1:13:20What Cooper Webb's 2025 Supercross Championship Meant
  17. 1:17:44Losing Chase Sexton to Geico Honda
  18. 1:21:20Eli Tomac
  19. 1:22:37What is Haiden Deegan Really like!?
  20. 1:26:21Untold Haiden Deegan Story
  21. 1:27:26Why Riders Leave the Program
  22. 1:30:12Star Racing's Next Champion
  23. 1:32:19Fist Handwear Ad
  24. 1:33:45Star Racings Biggest Rule
  25. 1:39:00Cole Davies Whoop Speed
  26. 1:40:59Millsaps Training Facility
  27. 1:42:20Best Rookie Season Ever!?
  28. 1:46:44Australias Next Champion!? Blake Bohannon
  29. 1:48:51What you Need to Know about Bobby Regan
  30. 1:54:01Haiden Deegan is like a Son to Bobby
  31. 1:54:44Outro

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