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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