Cooper Webb joins us for Chapter 378 of Gypsy Tales. Now a three-time Supercross champion, Webb heads into Anaheim 1 Supercross locked in and hungry, ready to battle for his fourth Supercross title.
Known as one of the most mentally feared competitors in Supercross, Cooper has built his legacy on resilience, pressure, and showing up when it matters most. You can never count him out. In this chapter, we dive deep into what makes Cooper tick, the mindset that separates him from the rest, and the untold stories behind his championship mentality.
We also break down the 2026 Supercross Championship, who Cooper sees as his biggest competition, and why he’s confident he can come out on top again.
A raw, honest look inside the mind of one of the greatest racers of his generation.
Gypsy Gang! Enjoy the show! — Remember to like, subscribe, and drop a comment below!
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00:00:00 Intro
00:01:11 Welcome back Cooper Webb
00:07:57 Fly Racing Ad
00:09:14 Struggles at KTM
00:19:30 Cooper Admits He Raced a Stock KTM
00:21:45 Doubt Fuels Cooper
00:26:24 SOTA Fuel Taste Test
00:27:32 Why Cooper Isn't Afraid to Fail
00:38:05 What It Took to Be a 3x Champ
00:45:33 Best Cooper Webb Yet?
00:49:25 Jett Lawrence Injured
00:53:34 Injury Plague in Supercross
01:06:24 100 Hours with Jo Shimoda
01:10:56 Drinking Beers Before the Main Event
01:16:42 Beating KTM and Chase Sexton Straight Up
01:22:39 Cooper Road to the Pros
01:31:29 Yamaha Ad
01:32:55 Coops Biggest Rivalry
01:42:31 Battling Eli Tomac
01:50:05 Why Cooper Hid an Injury
01:57:14 Inside the 2025 Supercross Title Fight
02:06:38 Out Smarting Chase Sexton
02:11:10 Inside the Mind of Cooper Webb
02:16:14 2025 Seattle Supercross
02:23:33 How it Feels Lining Up at A1
02:29:46 how Teammates Help Win Championships
02:36:00 Fly Racing's First 450 Champ
02:46:08 Buying Top Gun MX in North Carolina
02:50:20 Motosport Ad
02:51:29 Will Webb Race World Supercross
02:58:03 The Day Cooper Owned Motocross
03:03:00 Chasing a 450 Outdoor Title
03:07:45 Retiring from Pro Motocross!?
03:11:30 Can Haiden Deegan best Jett Lawrence
03:23:32 This is Why Jett Lawrence is so good
03:26:42 Cooper's Advantage This Supercross Season
03:31:46 Outro
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