CHAPTER 387 Ft. Gary Bailey

Gypsy Tales

Jase Macalpine

Society & Culture

4.6 • 564 Ratings

🗓️ 2 March 2026

⏱️ 196 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

Gary "The Professor" Bailey — the godfather of American motocross coaching — joins the Gypsy Tales Podcast for over 3 hours.

Gary was the first American to beat European riders in motocross (1969), designed the original Daytona Supercross track, built the very first supercross courses at Ascot Park, Houston & Dallas, and founded America's first motocross school. Over 55 years he's coached Travis Pastrana, Cooper Webb, David Bailey, Damon Bradshaw, Ryan Dungey, and countless others.

In this episode Gary breaks down Jett Lawrence's riding technique, whether Haiden Deegan should've moved to 450s already, Eli Tomac on KTM, what made Travis Pastrana untouchable in the whoops, an unheard Ryan Dungey story, the Evel Knievel era, and his 2026 Supercross predictions.

🎬 Join us for a special screening of 100 Hours with Jo Shimoda live and in person.

📍 March 6th in Indianapolis.

🎟️ Get tickets here:

https://us.gypsy-tales.shop/pages/premiere-screening

🧤 FIST HANDWEAR:

http://www.fisthandwear.com

CODE: GYPSYGANG for 15% off

👕 DIXXON x Gypsy Tales Flannel

🇺🇸 US: https://www.dixxon.com/products/gypsy-tales-flannel

🇦🇺 AUS: https://www.dixxon.com.au/collections/new-releases/products/gypsy-tales-flannel

🏍 MOTOSPORT.COM: https://www.motosport.com/?rstr=62946&ls=8vu&utm_source=roster&utm_medium=influencer&utm_campaign=-jasonmacalpine-62946

💧 Stay hydrated with SOTA Fuel — Order yours today:

https://sotafuel.com/products/sota-fuel-hydration-30-pack?variant=42103959945258

🛒 Shop Gypsy Tales merch: https://us.gypsy-tales.shop/

🎙 SUBSCRIBE TO THE PODCAST: https://www.youtube.com/channel/UCsBG…

📸 FOLLOW GYPSY TALES ON INSTAGRAM: @gypsytalespodcast

📩 Business Inquiries: ethan@gypsy-tales.com

🔥 CHAPTERS:

00:00:00 Intro

00:01:36 Welcome Gary Bailey to the Podcast

00:13:41 Why Using the Clutch is So Important

00:20:46 Tomac on KTM — Better Than Ever?

00:34:36 Jett Lawrence's Secret: Play Riding

00:54:33 When Gary Bailey Started Racing

01:02:20 Supercross Needs to Fix This

01:09:24 What Made Gary Bailey Fall in Love with Motocross

01:13:40 When the Americans First Beat the Europeans

01:31:01 Evel Knievel Changed Jumping Forever

01:42:22 What Track Conditions Make the Best Racing?

01:47:38 Should Haiden Deegan Have Gone 450 Already?

01:53:27 This Small Detail Improves Cornering

02:00:00 Why Travis Pastrana Was So Good in the Whoops

02:05:01 The First Ever Motocross Team

02:18:09 When Motocross Really Took Off in America

02:31:00 Coaching David Bailey

02:37:47 Teaching Riding on Your Toes in the Early 2000s

02:42:31 List of Greats Gary Trained

02:46:32 Working with Travis Pastrana

02:53:50 Travis Pastrana's FMX Career

03:02:22 Unheard Ryan Dungey Story

03:08:05 2026 Supercross Season Predictions

03:10:09 Closing

#motocross #supercross #garybailey #travispastrana #cooperwebb #jettlawrence #haidendeegan #ryandungey #davidbailey #elitomac #daytona #moto #mx #dirtbikes #gypsytales

See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Transcript

Click on a timestamp to play from that location

0:00.0	Every rider who made an impact on motocross had a coach, some pointing out lines, correcting
0:05.4	mistakes, and building the technique to go faster. Before coaching was an industry, before riding
0:11.2	schools, there was Gary Bailey. I was just blessed. I mean, why God blessed me with this? I don't
0:17.1	know. Jesus, it's been good life. Gary wasn't just a coach.
0:22.0	He was a racer first.
0:23.6	In a sport dominated by Europeans, he became the first American to beat them on American
0:28.6	soil.
0:29.6	That racing background shaped how Gary saw the sport.
0:32.7	He studied motocross like a playbook, filming every practice, every lap, breaking riding down into technique,
0:39.5	timing and intention. That approach helps shape his son, David Bailey.
0:43.7	I adopted him, so he's not my stepson, he's my child.
0:46.5	Yeah, right.
0:47.4	Doesn't that make him my child?
0:49.0	Yeah.
0:49.4	He does.
0:50.0	A two-time supercross champion and 250 motocross champion.
0:53.4	When I saw that he was taking a real interest in wanting to be,
0:59.1	not because I want him to be, he wanted to be the best, he wanted to win a championship,
1:03.6	he wanted to win the motocross of nations, whatever race he had put his mind onto it,
1:08.5	that's what he did he wanted.
1:09.4	And one of the writers who helped define the modern writing star.
1:12.7	Smooth, calculated,
	...

Please login to see the full transcript.

Previous episode | Next episode

Disclaimer: The podcast and artwork embedded on this page are from Jase Macalpine, and are the property of its owner and not affiliated with or endorsed by Tapesearch.

Generated transcripts are the property of Jase Macalpine and are distributed freely under the Fair Use doctrine. Transcripts generated by Tapesearch are not guaranteed to be accurate.