Bobby Regan/Gyspy tales

ohh_454
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Dunno if you guys have gave it a listen, but it’s a pretty good one. Two interesting things I heard Bobby say was that he had worked out a deal to sign Jessy Nelson for the 2017 season right before he got hurt at Unadilla. I thought that was pretty interesting and heartbreaking to hear for Jessy at the same time. The other thing is that he paid for Matt LeBlancs college after he quit racing. He stated something along the lines of he didn’t want to see him chasing lesser rides and not making it and offered to pay for his college. I thought that was pretty damn cool. I know most talk crap on Gypsy, but it was a good listen. 

 

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stewie94
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2/12/2026 8:51pm

Bobby to me is like moto’s version of Greg pop , they both do & say some slick shit just to fire the team up & get everybody motivated but on & off the court or in Bobby’s case on & off the racetrack he takes care of his guys 

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2/12/2026 9:15pm

Bobby mentions he’s paid for multiple of his riders college educations. Pretty damn cool!  

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Tyler D
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2/12/2026 11:15pm Edited Date/Time 2/12/2026 11:15pm

any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders on his payroll?

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DonM
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2/13/2026 5:47am
Tyler D wrote:
any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders...

any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders on his payroll?

You won't like what he said....

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The Shop

8tensolutions
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2/13/2026 6:26am Edited Date/Time 2/13/2026 6:26am

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

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davistld01
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2/13/2026 6:43am Edited Date/Time 2/13/2026 6:46am
It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's...

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

I doubt that any moto-media podcaster types like Jace...would dive into any of those topics or topics of that nature out of respect, or if they had any hope of luring more high-profile team owners/managers to sit for interviews in the future. 

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Mavetism
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2/13/2026 6:53am Edited Date/Time 2/13/2026 10:28am
Tyler D wrote:
any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders...

any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders on his payroll?

He said Deegan is the easiest guy he ever worked with and you could tell that he is a massive fan of him. Didn't seem like any of Deegans moves would be a big topic for Regan. 

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Flatliner
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2/13/2026 6:54am
It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's...

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

Sure, but you know they would have went over the ask-do not ask stuff beforehand.

 

Moto guys have it easy compared to stick and ball when it comes to treatment when underperforming.  I work with some guys who've played pro hockey in europe, and had two way nhl deals.  One day you're there, the next you're gone and nobody gives a rip.

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8tensolutions
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2/13/2026 7:33am
It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's...

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

Flatliner wrote:
Sure, but you know they would have went over the ask-do not ask stuff beforehand. Moto guys have it easy compared to stick and ball when it...

Sure, but you know they would have went over the ask-do not ask stuff beforehand.

 

Moto guys have it easy compared to stick and ball when it comes to treatment when underperforming.  I work with some guys who've played pro hockey in europe, and had two way nhl deals.  One day you're there, the next you're gone and nobody gives a rip.

I understand they would have covered it.  I was saying that because so many members here yell and scream about the media asking the "hard" questions, but if Jace would have done that he would lose future opportunities for interviews.  I am not saying that is right, but it's the way it is.

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ohh_454
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2/13/2026 8:38am
Tyler D wrote:
any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders...

any insight in the interview into how much correction he gives to deegan, if any? e.g. i.e. asking deegan to refrain from taking out other riders on his payroll?

Mavetism wrote:
He said Deegan is the easiest guy he ever worked with and you could tell that he is a massive fan of him. Didn't seem like...

He said Deegan is the easiest guy he ever worked with and you could tell that he is a massive fan of him. Didn't seem like any of Deegans moves would be a big topic for Regan. 

Yaa, and Bobby brings up the term competition a lot which would make me think he would be more upset with the riders that keep getting punked out over what Deegz is doing. He talks about heart a lot and brings up JMart, Webb, and Deegz, you can tell makes him happy. I would think his rider rolling over would piss him off teammate or not. 

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KurtJ99
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2/13/2026 8:52am

That was one of the best interviews in a long while. One of the most revealing things I learned was his long term commitment to the sport. The heartbreak of the passing of one of his riders early in his career. How he was both demanding and caring (i.e. college tuition), how he didn't have children but treated all of his riders like family. Even if you don't like Gypsy (for whatever reason), you ought to listen to this podcast to get a perspective of how he became both successful professionally and contributed decades of growth to the sport. 

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Racerman967
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2/13/2026 9:34am

Stealing riders? Is that code for spending more money for someone? Riders are independent contractors they will race for who pays the most

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Indy mxer
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2/13/2026 9:36am

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

Frd03
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2/13/2026 9:50am
KurtJ99 wrote:
That was one of the best interviews in a long while. One of the most revealing things I learned was his long term commitment to the...

That was one of the best interviews in a long while. One of the most revealing things I learned was his long term commitment to the sport. The heartbreak of the passing of one of his riders early in his career. How he was both demanding and caring (i.e. college tuition), how he didn't have children but treated all of his riders like family. Even if you don't like Gypsy (for whatever reason), you ought to listen to this podcast to get a perspective of how he became both successful professionally and contributed decades of growth to the sport. 

I wouldn’t say I didn’t like Jace but I couldn’t stand his podcast for a while. It was hard to tell who the guest was with how much he would talk/cut off the actual guest. I will say he seems to have gotten much better and the Regan interview was fantastic.

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gt80rider
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2/13/2026 10:04am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

Boy... kinda like our world leaders... if u only knew behind the scenes... you'd probably not feel that way... 

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2/13/2026 10:41am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

He graduated from LSU got drafted into the army during Vietnam was immediately put into a roll in the pentagon testing armament for aircraft then once he was out ran his fathers car dealership and still has them to this day. 

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DonM
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2/13/2026 11:01am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

gt80rider wrote:

Boy... kinda like our world leaders... if u only knew behind the scenes... you'd probably not feel that way... 

Explain...

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PNWMXer
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2/13/2026 11:45am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

gt80rider wrote:

Boy... kinda like our world leaders... if u only knew behind the scenes... you'd probably not feel that way... 

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-MAVERICK-
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2/13/2026 11:52am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

Car dealerships.

The Wolf Man
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2/13/2026 12:23pm Edited Date/Time 2/13/2026 12:51pm
It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's...

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

Bro interviews are the only 'interviews' Gypsy does...

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The Wolf Man
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2/13/2026 12:30pm

Stealing riders? Is that code for spending more money for someone? Riders are independent contractors they will race for who pays the most

Agreed, this is a professional sport operating in a free market.

If teams want to keep their best riders they need to provide better product and support and/or pay more money...

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DonM
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2/13/2026 12:41pm
It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's...

It was an ok interview and Bobby seems like a cool dude that loves the sport......but the controversial topics like the way they steal riders, Deegan's bike claiming incident at Lorettas, treatment of riders who don't perform etc etc were not asked.  Considering the criticism for moto media here, this is a bro interview at its finest.

Bro interviews are the only 'interviews' Gypsy does...

There’s the Hair Licker we know…..

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Kyzer138
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2/13/2026 3:59pm

Bobby throwing shade at Jcoop made me laugh.

For those who won’t listen, he basically said that if Jcoop didn’t jump the whoops he would win races lol 

KurtJ99
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2/13/2026 5:04pm

Stealing riders? Is that code for spending more money for someone? Riders are independent contractors they will race for who pays the most

When you build the fastest bike in the paddock, you don't have to steal riders. I remember one Washougal national when JCoop was still on 250s and I think the first 5 250s - the entire Star 250 squad - had the first 5 spots. Was quite a sight.

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Mavetism
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2/13/2026 6:02pm

Stealing riders? Is that code for spending more money for someone? Riders are independent contractors they will race for who pays the most

KurtJ99 wrote:
When you build the fastest bike in the paddock, you don't have to steal riders. I remember one Washougal national when JCoop was still on 250s...

When you build the fastest bike in the paddock, you don't have to steal riders. I remember one Washougal national when JCoop was still on 250s and I think the first 5 250s - the entire Star 250 squad - had the first 5 spots. Was quite a sight.

Every start that season looked pretty much like this (from 2019). 😂

s1200 072819Washougalracing0066 2
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joshd
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2/13/2026 6:27pm

Was a great listen. 

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ohh_454
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2/13/2026 7:17pm

Stealing riders? Is that code for spending more money for someone? Riders are independent contractors they will race for who pays the most

KurtJ99 wrote:
When you build the fastest bike in the paddock, you don't have to steal riders. I remember one Washougal national when JCoop was still on 250s...

When you build the fastest bike in the paddock, you don't have to steal riders. I remember one Washougal national when JCoop was still on 250s and I think the first 5 250s - the entire Star 250 squad - had the first 5 spots. Was quite a sight.

Mavetism wrote:
Every start that season looked pretty much like this (from 2019). 😂

Every start that season looked pretty much like this (from 2019). 😂

s1200 072819Washougalracing0066 2

Yaa after riding Deegz 250 at the des nations, JCoop was saying the previous model that he raced had more bark to it. 

Vet57
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2/14/2026 12:53am Edited Date/Time 2/14/2026 12:56am

images %281%29 12.jpg?VersionId=QlQZECmDFqZaKHZPmAa65RVRAll I know is this is one hell of a payroll...

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shane509
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2/18/2026 10:18am
Indy mxer wrote:
BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his...

BR is definitely good for our sport. I'm not a Yamaha guy at all. But I respect the hell out of what he's done with his team and riders.

Just curious though, obviously he's a very successful guy, in what business did he make his money?

-MAVERICK- wrote:

Car dealerships.

It’s just one dealership, Star Chevrolet in Wiggins. I live right up the road from it. Honestly, if you’re not paying attention when you drive by, you’d probably miss it. It just looks like a small-town dealership. They used to do a race report on the local radio the following week, I'm not sure why they stopped, but they still run radio ads. It’s actually a running joke in my family that when they win someone says 

“1-800 S-T-A-R B-U-Y.”

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