Gypsy Tales

Antonio Cairoli joins us for Chapter 382, and this is a special one. Antonio is a true legend of motocross, a 9 time World Champion who raced head to head with nearly every defining name of the past 20 years and helped shape an entire era of the sport. In this chapter, Tony walks us through his journey from growing up in Sicily, Italy, to becoming one of the most dominant riders motocross has ever seen, reflecting on his rise to the top, his championship years with KTM, winning multiple world titles on the 350, and the fiercest rivalries that pushed him to greatness. Now stepping into a new role with Ducati, Tony continues to give back to the sport that gave him everything, carrying forward his Italian heritage while helping shape the future of motocross through experience, leadership, and legacy.

Gypsy Gang enjoy this chapter and remember to like and subscribe so you never miss a new drop!

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00:00:00 Intro
00:01:15 Who's the GOAT of MXGP!?
00:04:48 Cash App Ad
00:06:25 What Herlings said about the GOAT Debate
00:12:13 Tony's Unique Approach to Training
00:20:35 Why Tony's Still Loves Moto
00:27:58 Aura Frames Ad
00:29:15 Growing up in Sicily, Italy & Falling in Love With Two Wheels
00:39:46 The Start of Tony's World Championship Career
00:49:18 Tony NEVER thought He'd be a World Champion
00:54:03 Signing with De Carli Yamaha (Tony's Breakthrough)
00:57:35 How Tony Became a Better Sand Rider
01:05:00 Jorge Prado's Rough Pro Motocross Season
01:06:19 Bubs Naturals Ad
01:08:11 Winning His First World Championship Race
01:13:47 Tony's Toughest Competitors
01:24:09 The Best Riders Tony Raced Against
01:28:07 Tony Knows He's the GOAT of MXGP
01:34:53 Adjusting to Life as a World Champion
01:47:01 Brunt Boots Ad
01:48:30 Racing the Americans at MXON
01:53:18 Is Stefan Everts an All Time Great?
01:54:28 MXGP Dominance for 6 Straight Years
01:58:14 Signing with KTM and Racing the 350
02:04:27 How MXGP Teams Operate Like MotoGP Teams
02:13:25 Why Tony Cairoli Switched Back to the 450
02:15:51 Men go to Mars Ad
02:17:30 The Real Reason Tony Retired
02:21:29 Tony on Racing in America
02:26:21 How MXGP Bikes Differ From American Race Bikes
02:28:36 It's a Massive Change! MXGP to Pro Motocross
02:31:29 The Ducati 250 Is Being Built!
02:36:44 Testing MotoGP Bikes and F1 Cars
02:45:17 Signing with Troy Lee Designs
02:46:20 Tony's Biggest Accomplishment
02:48:42 Closing
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Rickie Fowler joins us for Chapter 383 of the Gypsy Tales Podcast for an epic crossover conversation between professional golf and motocross. The PGA Tour fan favorite opens up about his toughest career moments, his deep love for moto, breaking down Supercross racers' golf swings, and how he helped change golf's image forever.

From his unwavering commitment to Cobra Golf to chasing the flow state on Tour, Rickie gives one of his most candid interviews yet. Plus, the guys dive deep into the 2026 Supercross season, Eli Tomac's move to KTM, Chase Sexton's switch to Kawasaki, Jett Lawrence's dominance, Haiden Deegan backing up the talk, and how Tiger Woods transformed the game.

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00:00:00 Intro
00:01:38 Welcome Rickie Fowler to the Podcast
00:10:25 Cash App Ad
00:12:02 2026 Supercross Season
00:17:09 Eli Tomac's Switch to KTM
00:24:37 Chase Sextons Switch to Kawasaki
00:26:27 Rickie Fowlers Commitment to Cobra
00:33:37 Motosport Ad
00:35:23 Jorge Prado's Career Bounce Back
00:41:10 Rickie Fowlers Toughest Moment
00:46:04 The Fine Line in Golf
00:53:49 Alpinestars Tech-Air Saved Justin Barcia
00:57:38 Rickie Fowler's Love for MOTO
01:01:59 Rickie Fowler Breaks Down Supercross Racers Golf Swings
01:15:25 Brunt Boots Ad
01:16:56 Rickie Fowler's Birdie on the 16th Hole
01:20:55 Why Rickie Fowler Doesn't Ride Dirt Bikes Anymore
01:26:26 Reaching the Flow State on the PGA Tour
01:32:59 The Best Rounds of Rickie Fowlers Career
01:38:34 Why Golf is so Entertaining to Watch
01:41:32 How Tiger Woods Changed Golf
01:46:00 Fist Handwear Ad
01:47:24 Golf Rapidly Grew During Covid - 19
01:49:51 Iconic Moto Movies
01:52:12 The Growth of Supercross
01:59:40 Jett Lawrence's Dominant Era
02:02:06 Haiden Deegan Backing Up the Talk
02:08:16 How Rickie Fowler Changed Golf's Image
02:15:41 Dixxon Flannel Ad
02:16:32 Rickie Fowlers Dream of Becoming a Red Bull Athlete
02:20:49 The Endurance Required to Compete at Golf's Highest Level
02:25:49 Motocross is So Gnarly
02:33:59 Predicting the Supercross Championship
02:37:20 Ducati Came in Swinging
02:38:24 Waste Management Open
02:40:47 Closing
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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!

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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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Brian Deegan joins us for Chapter 380. Brian Deegan has accomplished a lot in both freestyle motocross and business, but most importantly in raising a family and passing those lessons on to his children. Now Brian is taking a step back from his heavy involvement in Haiden and Hailie’s programs and sharing the knowledge he’s gained from competing, building business, and raising kids with his community. Introducing The General’s Army, a powerful network of high-achievers who share strategies, connections, and success together. In this chapter, we dive into everything Brian is doing with the General’s Army, talk about Haiden moving to the 450 class, and Metal Mulisha making a comeback and launching in Australia. Gypsy Gang, as always, thanks for watching. Drop a comment below, share this chapter with a friend, and hit subscribe so you never miss a new drop.

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00:00:00 Intro
00:01:04 Welcome Brian Deegan to the Podcast
00:01:33 General's Army
00:11:08 SOTA FUEL taste
00:12:42 Avoiding unhealthy foods
00:14:58 Brian sharing his knowledge
00:21:13 Disciplining his Children
00:26:15 Social Media / Speaking
00:29:56 Reading questions on the General Army
00:34:44 Why do you do what you do?
00:38:19 How much things have changed every decade
00:43:33 Working on your relationships
00:49:02 A message to motocross parents
00:56:14 Haiden still loving Moto
01:01:14 Investing in yourself
01:05:12 100 Hours with Jo / Money is suppose to come and go
01:20:00 God bless America
01:22:43 The Deegans fly private
01:26:43 Live calls with Brian Deegan zoom call
01:29:51 Brians involvement in Haiden's program going into the 450 Class
01:34:53 Deegan taking out Max Anstie
01:55:11 Haiden's changing the sport
02:03:58 The only person you can fix is yourself
02:13:58 Racing WSX
02:19:58 South African Motocross fans
02:25:38 Hows Haiden riding the 450
02:31:58 Wrecking rental cars
02:35:16 DEEGAN vs GYPSY Bike Build
02:42:34 Jo Shimoda Premier
02:45:25 More brands entering the sport
02:48:25 Electric bikes are taking over
02:51:25 Metal Mulisha expands to Australia
02:58:25 Haiden Deegan signs with Fox'
03:03:25 Haiden Deegan to the 450 Class
03:08:19 Closing

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Jason Weigandt joins us for Chapter 379! Jason is one of the most respected voices in motocross media a journalist who’s become a massive presence in the sport and a fan favorite across Supercross. What makes his story even crazier He never raced a dirt bike. So how did a lifelong moto fan go from the stands to becoming the main man at Racer X and calling Supercross races That’s exactly what we break down in this chapter. We dive into Jason’s journey the behind the scenes reality of motocross media and what it really takes to build credibility in the sport. Gypsy Gang, enjoy the show and don’t forget to like and subscribe below!

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00:00:00 Intro
00:01:16 Jo Shimoda 100 HOURS Announcement
00:02:21 Pod Starts
00:04:24 Dealing with Social Media Hate
00:05:37 World Supercross Commentary
00:17:34 Fans Don't Understand How Hard This Is
00:20:32 why everyone hates commentary
00:27:52 SOTA Fuel Taste Test
00:36:35 Appreciating the Gypsy Gang
00:39:07 Why I Quit The Podcast
00:58:34 Does Money Push Riders to Retire?
01:02:12 Brunt Workwear Ad
01:03:42 Top 5 Anaheim 1's of All Time
01:08:54 What Happen to the Party Era of Supercross
01:20:23 What got Jason into MOTO
01:27:23 How Jason Weigandt Got into MOTO
01:38:47 How Jason Learned to public speak
01:56:19 Jason's Path to Racer X
02:03:48 Jason's First Shot at Commentating
02:06:57 Being Overlooked for Years
02:14:53 Supercross has the best fans
02:29:14 Aura Frames Ad
02:30:32 Jason Weigandt's Role at Racer X
02:32:37 BlockBuster Turning Down Netflix
02:44:44 AI and Fake News in MOTO
02:55:55 Moto Fans want the real story
03:28:39 The Team at Racer X
03:37:21 Men go to Mars Ad
03:39:01 Justin Brayton
03:41:26 Supercross Racers Attention to Detail
03:53:11 Jasons Biggest Struggles
03:56:50 How to get a job in the Moto industry
04:08:16 The Early Days of Gypsy Tales
04:18:04 What makes a Great Leader
04:26:03 Closing

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