
Jamey Flannery was a winning off-road truck racer, who thought he was invincible until a dramatic health scare forced him to reconsider his life's priorities
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Kenny Wallace
Hello everyone and welcome back to Kenny conversation. Brought to you by i55 Federated Auto Parts Raceway park right here in Peveley, Missouri. Dirt racing every Saturday night. Okay, everybody, I guess everybody's my friend, but the man you're looking at right now is really a good friend, friend of the Wallace family. This is the great Jamie Flannery. Jamie, how are you doing?
Jamie Flannery
I'm doing wonderful. Kenny, how are you man?
Kenny Wallace
I'm doing so good. And I thought to myself, how am I going to introduce Jamie because there's so much to you. So I called one of your best friends in life, Stephen Wallace. Yeah. And I said Stephen, tell me about Jamie. So I, I asked my nephew Stephen Wallace, which is Rusty's boy. I said what should I say? And he said, uncle Kenny say this about Jamie. His racing career is really interested. He was teammates with the seven time NASCAR champion Jimmy Johnson in off road trucks. His dad was an extremely successful racer himself like Walker Evans status. And then of course I added this legendary off road truck racer and winning businessman Jamie Flannery, everybody. There he is. Where are you at?
Jamie Flannery
I'm in Atlanta, Georgia and we just pulled over in some waste management parking lot to do this interview. So we were actually, I bought Walker Evans as big coach a couple years ago. So we're driving that back to Wisconsin.
Kenny Wallace
Okay, this is going to be a loaded Kenny conversation, everybody. Like I said, winning businessman, off road truck racer winner, businessman friends with the great Walker Evans. We lost Walker last year, but let's start like this. I know you Too good. So I'm a little jaded. You look good. Your. Your T shirt is brilliant and bright, but you went through a recent health scare. Let's educate everybody. Tell me about this health scare.
Jamie Flannery
So we had. We went to Mayo Clinic in Rochester, which Rusty got me hooked up up there with his guy and got it checked out. And I had a bad valve and an aneurysm on one of my. One of my aorta tubes and got my. My surgery moved from Rochester to the Mayo Clinic in Jacksonville. And so I went and had. I went to Jacksonville, got open heart surgery. The surgery went terrible, terribly bad, and I started bleeding internally. I was only home for five hours. Veronica rushed me back to the hospital, and. And my blood pressure was 50 over 30. I died for seven minutes on the table. And I had one of the best surgeons in the country, and he brought me back to life. So it's. It's amazing I'm still here. So.
Kenny Wallace
Okay, Jamie, I want to let you know I love you. I'm with you. My whole family. My Uncle Gary got helicoptered out of Yellowstone national park with heart issues. My dad died, you know, had a triple bypass. My brother Mike had his chest broke open. So us. Wallace's, we know all about this, too well, so I'm with you. How did you know there was something wrong with you? Certainly you were going along one day, as far back as you can tell. What started happening to you that you said, there's something wrong with me?
Jamie Flannery
Well, it started about four years ago. I always liked wearing cowboy boots, and I couldn't get them on anymore, so. Well. Well, I was still able to go 100 miles an hour in my businesses and. And do what I do. I just put a different pair of shoes on, just wore a different pair of shoes, thinking it might. Well, it just go away. And that's not what happened. I slowly would climb a set of steps or get up in excavators or just something where you started working your heart a little bit. And pretty soon, I'd run out of breath just climbing the stairs in my house, and I'm like, veronica, there's something horribly wrong. And I want to get my health insurance switched to Florida because I become a Florida resident. And once I got that done, I went to Mayo, and then I got everything checked out, and they discovered I had this aneurysm and a bad valve, that I was born with this bad valve. So basically, the blood would pump up in your. In your arteries, and then it would flow back down, and your heart had to Re pump blood back and forth, and. And it was. I'm like, okay, well, that sounds good. And met the surgeon, and everything was. Everything was moved to Jacksonville, and away my surgery went. So that's kind of the story behind it. Yeah.
Kenny Wallace
You know, 2012, you know, I was doing these NASCAR physicals. Every year I had to get a NASCAR physical. And up until then, I was just being me. They said, hey, your sugar's a little high. Scared me half to death. And I tell everybody I'm still Kenny, but I'm changed forever. I eat like a rabbit. I do my very best, so I know a little bit about these things. I'm sure you're still Jamie. You're still Jamie, but you're going to be changed forever. Tell me about your new life. What type of regimen are you going to do to help your health?
Jamie Flannery
Well, the first thing is to watch what I eat a lot closer and less. I can probably cut my portions down. And your nephew Steve said, at the best, he said, you know, we. We can just pull the choke out and eat half as much as we used to, and that's still going to be plenty. And he's right. And. But for right now, I'm trying to get my muscle strength back, and so I'm. A lot of things don't taste good to me, so I try to just eat whatever I can just to get everything working back properly in my. In my system.
Kenny Wallace
Okay, so your health is back on track. You're still Jamie, you're still rocking and rolling, but, yeah, I'm with you, buddy. And. And the Wallace family has. Has been through these situations. All right, Are you ready to celebrate yourself? I'm gonna. I'm gonna help you.
Jamie Flannery
Okay. I'm ready.
Kenny Wallace
Okay. You know, I have my big brother, Rusty, and Rusty and my dad, the great Russ Wallace. They defined me. My dad won 400 races in the Midwest around St. Louis. Then along came my brother. So we share a lot in common. You have your. Your dad, the great Jack Flannery. Your dad was so good off road truck racing. Just tell me about your early beginnings around your dad growing up in Wisconsin.
Jamie Flannery
Well, we. We grew up around short course racing in Wisconsin. And when I was in. In 1979, I think was the first year that I got to go with him as a. As a young kid, you know, to. To go to Riverside Raceway, and that was the big short course race that. The famous Riverside Raceway. And. And so we really look forward to going out once a year and competing against Walker and Ivan Stewart and all of the off road racing greats. But my dad was a fierce competitor with them guys every year that we went out there and that was kind of the, the start of my racing was working on my dad's trucks, learning how to set them up, doing shock work, taking the shocks apart, putting them back on, you know, just, just working on the trucks a lot. And, and that's kind of how I got started, is just kind of following my dad around the country.
Kenny Wallace
I want to mix and match here. I, I find you really interesting from the standpoint that we all know our family, we know Roger Penske and Roger Penske was a great race car driver. And then he decided, hey, my business is doing really good. I need to slow up my racing and I'm going to take care of his corporation. Well now the rest is history. Roger Penske, one of the most wealthiest people in the world. He owns the Indianapolis Motor Speedway. So, you know you've got some great businesses. And at what point did you start mixing off road racing with your great business?
Jamie Flannery
Well, we always, our family was always in the logging business. So we took our sponsorship money from General Motors and everybody we got. And we as a family, we worked very hard and we probably, I would say triple the quadruple the sponsorship dollars that we stuck into my dad and mine race program. So. Which enabled us to have the best equipment in the business. And then in 1999 was our last year of, of off road racing. And then I started in business myself.
Kenny Wallace
Yeah, and boy, you're really good at it. We're going to celebrate your business in a little bit. So you know, up there in Wisconsin, I, I just, you know, I just never knew that logging would be such a big deal. And I'm lucky to know you. How is logging such a big deal up there? Is it the lakes? Is it the country?
Jamie Flannery
It's, it's just the vast amount of timberland that we have in the state of Wisconsin. The, the northern half of Wisconsin all the way to the up is just the, it's probably 90% wooded land and lakes and, and our state is beautiful and logging was a big industry and a lot of the paper, paper mills have, have went overseas and crippled and crippled the logging business. And that's, that's when I decided to make a move and, and get into the storm business and the rock business, the rock quarry business, crushers and excavators and all that kind of stuff.
Kenny Wallace
Listen up kids. This is the great Jamie Flannery from Wisconsin. And as we look around, all of auto racing Whether it's dirt racing, NASCAR racing, there's somebody that's got a business and that's what supports all of our racing, whether it's Ed Petrov, Jeff Hoker. We find a lot of these people. Jamie, you might not know these guys, but they support our dirt racers whether it's Lucas Oil or World of Outlaws. And these are great conversations. That money does not come out of the air. It comes from businessmen like you. So thank you for telling us that, that business side of you. Okay, I want to have a little fun. I want to go into the racing world and we're going to keep talking about your dad and Walker Evans, but let's go to something that just really sticks out at me, right? Jimmy Johnson, our seven time NASCAR champion. When did you come across him? And how in the world did you end up being teammates with Jimmy Johnson?
Jamie Flannery
So it was, it was real weird how it happened. I was ready to, I think I was like 15 or 16.
Kenny Wallace
Oh my.
Jamie Flannery
And. Which was a long time ago. I'm 53 now and I, I just decided to jump on an airplane and Chevy was my dad's sponsor. I had not been racing yet myself and I, I wanted to go to a Mickey Thompson stadium event which Rick Johnson drove the stadium truck and Jimmy drove the other stadium truck, which I
Kenny Wallace
didn't even real good and I didn't
Jamie Flannery
even know who Jimmy was. I know Rick at the time drove a stadium truck, but I really never heard of Jimmy because Larry Ragland drove the truck a little bit before Jimmy did. And so I just fly out to Denver. I didn't even tell anybody I was coming. And John Nelson, he run the Chevy stadium program for gm and I showed up out there and they all welcomed me in open arms. And I, I become very good friends with Jimmy and he's a, he was just a super nice guy and he's like, well, Flannery, what are you doing next weekend? I said, I don't know. He said, you want to go to Las Vegas with me? I'm racing in Las Vegas at the next stadium race. So we hop in his van, it's an a team looking van and we, we're traveling across the country together and, and we stop in Las Vegas and Jimmy did very well. I think he ended up winning the, the last stadium race and I think that was it. And then he's like, well, if you ain't doing nothing. I said, I ain't doing nothing. He said, you want to go to California with me? I said, yeah, I'll go to California with you. And so we traveled out to his house and stayed with his mom and dad. And at that time Jimmy, Jimmy lived on the side of his mom and dad's garage and I slept on the bottom of the futon bed and he slept on the couch across from me. And it was a, it was a great experience that, that we got to hang out together for probably a month and a half and I never went back home. My dad's like you ever coming back home to go to work? I said not as long as I can get away with it. So that's how I met Jimmy. And then he come back and Herb Fischl.
Kenny Wallace
Now we're getting somewhere.
Jamie Flannery
Chevrolet. Yeah, the, the, the Chevy Commander. So Herb sends Jimmy back to commentate for ESPN and our short course series back in the Midwest. They didn't have any, any place to put Jimmy at that time and race cars or trucks or anything so he was, he would just go around and interview the drivers and keep his face in front of the camera and, and then the Herzogs come along and put him in an off road truck and Jimmy was very, very dominant in an off road truck. He, he could really wheel one of those things like nobody we had ever seen and, and he give my dad all he wanted. My dad raced a four wheel drive and Jimmy raced a two wheel drive and Jimmy often beat my dad with a two wheel drive truck. Not all the time but there's some circumstances that, that he, he, he did beat my dad several different times. He was very fast and very good and the Herzog had, the Herzogs had superior equipment at that time. So Rod Millen built the truck for Jimmy and Herzogs and it was just a first class show.
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Kenny Wallace
You have a unique ability. You're a good man. You're always bragging on others. I just want to let you know that it was. It was. And I've told this story before. It was Darrell Waltrip's wife, Stevie. She said, kenny, you do something that's strange that we don't ever hear before. You talk good of others. It's very nice of you. I've been around you for a long time, and you do have the unique ability to remind us all where Jimmy Johnson came from. But listen, this is about you, and this is part of your journey. Don't you wish sometimes you just had a camera back in those days? And look, look where me and Jimmy came from. You know, we might have had a logging business, but look at this journey. Sleeping inside of a. I mean, those were the days, right? The journey.
Jamie Flannery
Well, there's some of it that I wish that wasn't on a camera
Kenny Wallace
that
Jamie Flannery
me and him did together, but we. We had a ton of fun. But I. I wish I would have had, you know, some pictures of, you know, going to the last two stadium events that Mickey Thompson ever had. I got to go to both of them with Jim, with Jimmy, and that was very special.
Kenny Wallace
You know, I like to keep everything right at an hour. So, you know, there's a lot to talk about. But the great thing about Kenny conversation is we can skip around. So, you know, we talked about you growing up in Wisconsin, the logging business, your dad being a hall of famer, a superstar. Let's jump forward. It seems to me after being around you a lot, Walker Evans is like your second father. Am I close or. You have a one.
Jamie Flannery
You.
Kenny Wallace
You had a wonderful relationship. We lost Walker. Tell me when you met Walker and how that started.
Jamie Flannery
Well, when I went to Riverside when I was a little kid, I think I had been there four times with my dad. And then we got to go to Walker's house and I finally got to meet him. And then he come back in 1988 to Crandon and some race got canceled up in Canada, and he brought all his stuff to Crandon and that was his first time coming to Crandon. And he never quit coming after that. So he kept his truck and we kept his truck in our race shop, which we were the factory Chevy team, and he was the factory Dodge team. But we got along that. That good. So I. After 1988, I got to spend a lot of time with. With. With Walker doing different things. Flying in his airplane with him, just going to his house and. And it. Then it seems like when my dad passed away, you know, Walker just kind of picked me up and took me to Africa and other things.
Kenny Wallace
Yeah, I know it's emotional, buddy. I'm sorry about that. You're going through a lot right now. You. You know, when you come out of surgery like that, it makes you emotional. And then we lost Walker. I love you and hang in there with me. You know, if Rusty was here right now, he'd say, franny, straighten up now, buddy. We can do this. Yeah.
Jamie Flannery
Yeah, but I hear Rusty. Rusty picked up after Walker.
Kenny Wallace
That tells you. That tells you what a good person you are. Everybody loves you. Your life is to be celebrated, and that's what we're doing right here. Show me your girl. Where's she at? Tell her to come in here. Get up. Get over there and give him a big hug. Oh, of course you're wondering. Yeah, yeah, yeah. Thank you, guys. I know this is emotional, and, you know, this is one reason I wanted to celebrate your career. I thought, my God, Jamie's done so much. We got to talk to him. Okay, so the great thing about Walker Evans is he reminded me of my dad. He was no bullshit. He was hardcore. And I call it tough love. If you want to get your feelings. If. If you don't want to get your feelings hurt, don't be around Rusty Wallace. Don't be around Walker Evans because they gonna jam it right up your ass. And you either going to accept it and be better or you're not.
Jamie Flannery
So I do know.
Kenny Wallace
I do know this about Walker, and I grew up around what Rusty calls tough love. It. Walker was so successful. What do. Do you remember any tough love lessons that. That Walker taught you? Was there anything that you use right now? It don't even got to be tough love, but what are some things that Walker that you instill in your life to this day?
Jamie Flannery
Just his drive that he had was incredible. He started his shock business at 60
Kenny Wallace
and probably sold it for millions and millions. A lot. You know, they. They say, kenny, don't talk about religion or money. I'm like, hold on now. We're not gonna say y.
Jamie Flannery
That could start a business like that. 8,000 shocks a week. It's incredible for Polaris at 60.
Kenny Wallace
60 years old.
Jamie Flannery
Started it.
Kenny Wallace
He started it. And wow. That's incredible. Okay, let's lay off a Walker. I know I, I realize how, how hard that is on you, but, but you make me bring Walker up because everything we talk about. I'll tell you what, I'm going to call an audible. We'll come back to Walker later because we're going to talk about Africa. Okay?
Jamie Flannery
All right.
Kenny Wallace
But not right now. We're going to give you a breather. Let's, let's go to your dad. And hopefully that doesn't get you emotional, but I guess it will. Okay, let's, let's forget about all everybody for a little bit. Let's go, let's go straight to Crandon. Okay, here, here's what I want everybody to know. Crandon, Wisconsin, home of the biggest off road truck race in America. It is the Daytona 500 of off road trucks. Crandon, Wisconsin. World championship. 70,000 people. My brother Rusty, of course I joke about myself, my brother Rusty, but Rusty tells me how big this event is. You eventually buy Crandon. But let, let's start with your earliest memories of this Daytona 500 of off road trucks. How far was Crandon from your house? Was Crandon a religion to you? Was it your church? Tell me about this, this Crandon, Wisconsin.
Jamie Flannery
So our town is only 1800 people and the race is basically the only thing that happens there. There's nothing there. We have a race in June and we have a race in on Labor Day weekend. The one in June is much, much smaller. But the, the race on Labor Day is really. It's like the Indianapolis 500. You know, it's something that fans and people do year after year after year after year. It's just something they plan their lives around. So it's. I live there my whole life and you know, I started out when I was about 8 years old picking rocks on the racetrack. There'd be 10 of us kids lined up and we'd just go down the racetrack and throw rocks off the side of the racetrack. And that's how we started. And then my dad, the first year he raced, he had a Mustang Mach one that my grandpa went and bought him and he went and tore the whole interior out of this brand new car to race it at Grandin and build up the. And I think My dad was fifth. I think he was 15 and, and had to fraudulently, you know, scam the paperwork so he could get in and race. But. And then I think two years after that or a year after that, he got a Ford pickup from My, my uncle that he, that he fixed all up and, and then he was. The Crandon started out as a 25 mile loop. And today the course is a mile and seven, eight. So everything happens in front of you. But years ago when my dad started, there was. It was basically loggers racing against one another.
Kenny Wallace
Yeah.
Jamie Flannery
And there's a group of old guys that knew every cut across road and everything on this 25, 5 mile loop they would make. And my dad said he knew he was leading the race because there was no tracks in front of him. All of a sudden it'd be like Junior Johnson cutting the course and here six tire tracks are ahead of him and then he's got to pass all these old guys. But he had a fast truck and faster than anybody else had. So he won a lot of the early races and that's kind of how we started.
Kenny Wallace
I, I find that our local racetracks define us. You always hear great racers talk about where they come from. Whether it's Kyle Larson, Rico Abreu and sprint cars out on the west coast or Placerville or you know, things like this. Now I want to brag on you a little bit. You are a champion at Crandon's Governor's cup in 1998 in a four wheel drive Chevy truck. Is that right?
Jamie Flannery
Yes.
Kenny Wallace
Tell me about that time. You're a badass.
Jamie Flannery
Yeah. I think in 1998. Well, what happened was, is we hired a guy from California that come out and run our race team. And he used to. He built Larry Raeglin's desert trucks. And he helped Nelson design all Jimmy and Rick Johnson stadium trucks. So we hired him to come out to, to Wisconsin. We built a new shop in Wisconsin Dells and he built me a new truck that was just superior. I mean it was, it was bad to the bone. And I, I was in 98. I was, I was pretty young. So.
Kenny Wallace
You were ball, you were ballsy.
Jamie Flannery
I had no fear. And I. It was a four wheel drive. So I got to race against my dad and Walker. And in 1998 and 99 I made their lives pretty miserable. I won, I think in 98 I won 11 out of 16 events that we had that year. So. Yeah, so that was pretty gratifying. To be able to do that. To beat those guys is tough. And Rob McCachern and he's a. He won the BA1000 the last three years in a row. He was back there racing with us and several other really good guys at that time. And, and I, I want that in 98, I think it was. I won 11 out of 16. So
Kenny Wallace
I've been, I want to, I want to say something. I've been around you a lot, but I've never been able to talk to you. Now I see why you're a successful businessman. You're reminding all the kids out there that want to be great racers right now what it takes. You talked about the man coming in you. You have to have good equipment, you have to have smart people around you. The days of going, I won with no money. I had nothing. Those days are over. And that, that's why you're successful in business because you know, you got to have a winning formula and that's what life is all about. Was it your dad or your mother that instilled this in you?
Jamie Flannery
I would say everybody as a whole, you know, just watching Walker and John Nelson and Herzogs, I got to be around those. And those guys are big time business today. They're, they're a gigantic corporation. The Bill Herzog which has passed away, I knew him very well. And Randy and Stan Herzog, they were very successful business people. And I got to be around people like that as Rusty was around Roger Penske. You're like a sponge around these people and you want to know what drives them to success. And that's how I am in business today.
Kenny Wallace
Yeah. And Rusty has taught me a lot. And you and him get along so good and share something funny with you about this subject. You know, Daytona, Talladega was Rusty's nemesis. And, and I'll never forget, he got aggravated one day and he said, damn it, I need the fastest race car and the fastest pit crew for Daytona and Talladega. And I'm like, hell yeah. You know, they don't pay money for having the slowest pit crew in the middle of the pack car. You, you know, the, you know, Earnhardt, Gordon, Dale Jr. All these guys that are successful, those tracks later on in life, you realize when Dale Jr. Comes on dirty Mo media nowadays, it's like, oh, and that's the rest of the story. No wonder he was winning all those races. You know, you had, you know, Tony Yuri Jr. Tony Yuri Senior. They're telling all these stories. You know, he had a special air cleaner. But I wanted to brag on you that you bleed praise. You praise other people and, well, you were a badass. And I just want to acknowledge that and want to let everybody know.
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Kenny Wallace
Let's. Let's keep on rolling here. As I dug into your past, I saw Uncle Cliff's name come up. Tell me about Uncle Cliff.
Jamie Flannery
Okay, so Cliff has run the Crandon race track from the beginning, and he's. He's put his life into Crandon Raceway. My dad was the racer. Cliff was the promoter. You know, the. The guy behind the scenes that, you know, built the tracks. And. And really he's the one that kept Crandon going for the racetrack for that many years. And it was a lot of work to really get it rolling. And then they bought their own piece of land. So Cliff, you know, got this thing along, which up until the early 80s, it was. It wasn't, you know, factory teams or nothing like that. And then. Then when Walker came in 1988, that changed. And then every. A lot of people from the west coast started coming out and bringing better equipment. The racing got faster, it made us get faster, and, And. And then, you know, the racetrack really accelerated. But Cliff always had the vision to build this building and then fix this up. And. And they had to do it over the course of a long time because it was hard to sell the racetrack when the racing wasn't maybe quite as good. You know, today, it's. It's like going to a NASCAR race. I mean, these trucks are a million dollars a pop. They got 950 horsepower, and it's serious. And. But Cliff is the one that's been behind the scenes all the time, and me and him kind of bought the racetrack together, and now he pretty much owns it solely. And. And it's. It It's a good thing.
Kenny Wallace
So Cliff is to be celebrated. You're telling me back in the mid-80s that he kept craning going when it was. Are you saying Cranin could have died out, but Cliff kept it going?
Jamie Flannery
I would say that's very possible. I mean, you never know the outcome. But he, he's the guy behind the scenes that kept the nonprofit organization together. And they didn't have the money to pay employees. And, and Cliff's the one behind the scenes. Him and Dennis Rosa that went and bought the 300 acre farm. And then once they own the land, then they had a foundation, then they could start building things slowly, one, one thing at a time and keep getting it better and better. And that's what they did. And here we are in 2026. You know, I think Crandon's been racing for 53, 54 years now.
Kenny Wallace
Okay. I have a method to my madness. We're going to celebrate your business. Then we're going to come back to Crandon when you ended up buying it. And, and obviously now you're saying you don't own it anymore. But let's, let's go back to your businesses. I want to brag on you now. I'm gonna tell you what I see and you tell me what you do or don't have. You're a businessman. In, in my, in my brain. You clean up natural disasters. It's pretty incredible. You have some 40, 50 trucks. The government calls on you. We just had the big ice storm in Biloxi, Mississippi. You're down there. I see you have, what is it? Flannery contracting? Is that the same thing? Flannery trucking, Flannery cycling. Now you're getting into the gravel. Tell me what all you got. You got a lot.
Jamie Flannery
There's a, there's a lot of pieces and it's growing rapidly. The storm business, I mean, is pretty big. And so basically what the storm business is is when a hurricane hits, let's just say Volusia county around Daytona. Volusia county is huge. The city of Jacksonville is huge. The city of Jacksonville has 5,500 miles of city streets. So when a Category 4 hurricane goes across Jacksonville, you need six, 700 trucks. I have 20. It people don't realize how big of an operation it takes. In 20, 25, there was two hurricanes that come through all the way from Sarasota, Florida, all the way through Asheville, North Carolina. The state of Georgia was tore up. And it took every person we had in the country that had anything to Pull us all together to get that mess cleaned up.
Kenny Wallace
Hurricane Helene.
Jamie Flannery
Hurricane Helene. I was in. I worked in Asheville. I cleaned. Me and a friend of mine cleaned the county up and the city of Asheville. And I was there for nine months, living in a bus. So
Kenny Wallace
we're gonna have Charlie drop some pictures right now of these bad boys. So what you're looking at right now, everybody, is massive trucks. But I always like the little man that's got the. The little, you know, deal in the back where he's picking up the stuff he's putting it in. You got the truck. He got the big trailer. Jamie, these things are monstrous. And you got 20 of them.
Jamie Flannery
They. They are. They're. They move a massive amount of stuff in a hurry. A dump truck hauls 20 yards in. My debris trucks haul 150. But you're hauling each. They're hauling brush and houses. We dug semis out of rivers in Asheville. Any. Any, you know, we. We go through and we clean it up from A to Z depending. Every one of them that you do is different. And. And then about six years ago, I. I bought. My grandpa passed away, and I bought the family business out from my aunts and my uncles, and that's how I got into the dirt and the rock business. The real reason I bought it was to be able to employ my storm guys when we weren't doing a storm, to keep my people. So I bought the rock business the first year. I. And concrete business. We own the. My grandpa owned the concrete business in Crandon, and he owned all the equipment, and he was like the. He was like the guy in the small town that owned everything. So I bought. I bought the dirt business out. In the first year, I didn't care for it too much. The second year, I kind of started to like it, and the third year, I really started to like it with the crushers and the rocks and selling, you know, buying. Buying pits. Selling pits. And I'm about ready to buy five more now. So with that being said, that the dirt business is going to grow tremendously. So I'm going to have a circle all the way from Wausau, which, you know where that's at. Yeah, from. Yeah, right. Yeah. So it goes all the way from Wausau to Crandon, and I'll have pits scattered all over in between there to service people and highway projects. And. And I. I don't want to get into doing so much of the work out in the field. I just want these pits and to keep these crushers Going and sell the material.
Kenny Wallace
So we're talking to the great Jamie Flannery, everybody. Legendary off road truck racer, Crandon, Wisconsin. But I want to dig into something right there. You said. I hear this a lot. You said at first you really didn't like the dirt business. It was. That was because. Is that because you didn't understand it? Did you get smarter at it? Is that why you like it now? Because you got smarter?
Jamie Flannery
That's right. I figured I hear it all the time that when I got in there, I didn't know. I didn't know how to run a lot of the equipment and didn't understand it. So the first thing I had to do, I got a very good foreman. His name is Brian Wilson. And he has, you know, he had. So I kept him on right for my grandpa. So he ran the business for 20 some years for my grandpa. And he, he was able to teach me a lot about things. Bidding jobs, concrete and the more. And. And then I started making money in the storm business a lot. And it allowed us to put new concrete plants in new concrete trucks, buy new dump trucks, buy new crushing equipment. And pretty soon we have this elite equipment now. And when I bought it from the family, my grandpa had it for years. A lot of it was older stuff that, that we just. That we just kind of got rid of.
Kenny Wallace
So, yeah, I love.
Jamie Flannery
So that's kind of the story behind it, how I got into that. And you know, in the. In the late 90s and the early 2000s, I phased out of the logging business because I could kind of read the writing on the wall of where the logging business was headed. And today it's. It's really struggling, I think, all across the United States, not just in Wisconsin.
Kenny Wallace
Yeah. I want to brag on you a little bit about your badassery. You know, there's people that, they think they're clean. And I'm like, no, you're not clean. This is clean over here. You know, Roger Penske, everything he has is first class. Rusty Wallace is over the top and so are you. You have that ability. Everything you do, all your homes, all your trucks, all your businesses are first class. Nicer than nice. Where did that come from? Was your dad like that? Who taught you that?
Jamie Flannery
Yes, he. He was very anal about, you know, everything just had to be just right. And then Walker was the same way, but worse. Yeah. Oh, yeah. Oh, boy. You hang around them guys, you learn real quick. And I can remember washing my dad's pickup when I was a kid.
Kenny Wallace
Yeah.
Jamie Flannery
Eight years Old. If there was any bugs on the front of his pickup, you washed the whole pickup again, not just the bugs off the front. And he made sure you did it again so that you did stuff correctly the first time and it didn't take a second time.
Kenny Wallace
My dad would say the scrubby Dutch, they called people in St. Louis. Every Sunday they'd be on their hands and knees cleaning their porches. And then dad, you know, my job was to clean the kitchen and the living room. Every day after school, he'd come in and run his hand across the top of the refrigerator. So that's. I grew up with Jamie. So if, if you see me tweaking a little bit, me and Stephen, it's because between, between my dad and Rusty, we're maimed. You can never be clean enough. It can never be clean enough. It just never ends.
Jamie Flannery
And.
Kenny Wallace
But it's millions and millions of dollars worth of equipment. So why not take care of your stuff?
Jamie Flannery
Take care of it and it for me. I mean, you've been to my place in Florida and beautiful. It goes to the same thing is everything is like Roger Penske, Rusty Walker. Everything has got its place. Everything's got to look a certain way. The truck's got to be parked in line, not 14ft further because I'll make them come back and park them properly. Because I don't want to be a sloppy debris business type guy. I want to be in the elite guys with the Datsuns. And there's, there's, there's Roger Penske's in the storm business too. And I want to be, I want to be one of those guys.
Kenny Wallace
So there's a great story about California. A kick ass guy out there says, you know, if you get up at 8 o', clock, you ride to work with all these junky cars. He says, if you get up at 4 o', clock, you're riding with all the Ferraris and Mercedes Benz Porsches. So get your ass out of bed and you can, you know, that's when all the hot rods are going to work. The lazy people, they're driving all the junkers.
Jamie Flannery
One thing that I've learned is nobody's going to give it to you.
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Kenny Wallace
I think I got you toughened up a little bit. We're going to. We're going to go back a little bit. Okay, let's go back. I'm sorry to. I'm sorry to rough you up so much, but such a part of your life. So my method of my business was to explain to everybody where you made your money. You're a great businessman. You decide to buy Crandon. Okay? You buy it, you got it jacked up, it's doing good. Then you decide to sell it. Tell me that time in your life when you bought it, when you sold it.
Jamie Flannery
Well, what happened was, is I had the offer to purchase and I was just about ready to. I had all the money in place to buy Crandon. And I ended up. I did not close on the deal. And I went and seen my uncle Cliff. And at that time, I was going through a divorce. So I just. You know, Crandon is a historic place. And the last thing I wanted to do was get it snarled up in some divorce that. That possibly something could happen to our crown jewel in Crandon. And that's the racetrack. So I went out and seen Cliff and I said, cliff, I can't close on this racetrack. I said, I'm too worried about something may happen in my divorce. We might lose this thing. And I said, let's just leave it where it's at for now and let's revisit this later. I said, it's going to be the best. I said, I can bring all my equipment out here. I can help. You know, we can keep this going. And. And it's secure where it's at, so let's leave it where it's at for right now. So then a few years later, Cliff comes and sees me. And I go to the bank with Cliff and I said, cliff, we'll just put this in your name. And so I put the money up for the down payment to buy it out of the nonprofit organization. And we got all the club members together. And then and then we ended up buying it together is what happened. And it got put into Cliff's name. And then Cliff and kind of his kids took the whole thing over and basically give me some of my money back. I still got some coming, but that's kind of the story about me and Crandon and the ownership of it.
Kenny Wallace
Man, you're a champion. You're unbelievable. I know. That story is personal. People will love you for telling that. That is so awesome. And what I took out of that is you love that area so much that you just didn't want to mess it up. So thank you so much. That is. That is. That is really incredible. Okay, so here we are. We're caught up to this day. You know, that's what Kenny conversation is about. We, we celebrate you. We know where you come from, heroes in your life, whether it's Walker, your dad Jack, Uncle Cliff. You're good friends with big brother Rusty. Now let's have a good time. Now these motorcycles, you know, I just got off the Kyle Petty charity ride. Now I got you smiling. He's smiling, everybody. If you're listening on Dirty Mo Media podcast, this is was a little heart wrenching to go through his health and losing the great Walker Evans. But now we're. Now we're riding motorcycles as a celebration. You're still working hard, you're still making money. Rusty says that he's racing in NASCAR at Dover and president at the time, Mike Kelton says, hey, Wallace, go out to Sturgis with me. Rusty goes out to Sturgis 25 years ago or whatever it was. He meets Walker, he meets Don Pradome. And here we are, we got southern country customs. We're building the most beautiful badass to Ferrari of motorcycles. And you have some of those motorcycles. Tell me about this motorcycle life that not just you, but myself, your girl, my girl, we're all living it. Now tell me about this.
Jamie Flannery
Okay, so Walker had tried to get me to go out to Sturgis, I would say five years before I went. I wasn't a bike rider.
Kenny Wallace
Me neither.
Jamie Flannery
I had a bike, but I never rode it. And so I had this little blue custom bike and I'm. I was three sizes too big for it. My kneecaps almost drugged the ground. Go to Sturgis and I'm riding with Rusty and Walker. And the first day. Now, mind you, I never rode a bike much in my life. Maybe on a 20 mile ride or something, we go 246 miles and I'm on this piece of blue bike that I thought was cool till I tried to ride at 246 miles. Yeah, I wanted to push that thing off of a cliff. When I got back, I was hurting. The last 150 miles was just grueling. I got back, I sit on the picnic table, I got drunk.
Kenny Wallace
Yeah.
Jamie Flannery
Drinking beer. And I'm sitting there by myself trying to get it back together after getting beat to death on this little blue bike all day long. So I'm like, I met Steve and I Matt Rusty out there and I see these beautiful bikes are building. I'm like, well, if I want to be a part of this, I'm gonna a have the good equipment. And I can see how these things are riding and the power they got and, and they're absolutely beautiful. So I think it was maybe the second year I went out there is when Stephen come back to Crannon the first time by me and he brings them bikes back with him and I'm, I'm riding around at Crandon on one of these bikes and I'm like, I gotta have one of these things. So anyways, I ended up buying one from him and I, I just ordered two more new ones from him. He's learned a lot over the last five years. So I bought one of his first ones that he had, which he totally refurbished it last winter. And now I'm, I'm buying two new state of the art bikes just for friends to ride if they don't have one or whatever. So we gotta, we gotta keep him building bikes.
Kenny Wallace
Yeah. You know, I, I can't help but to say a little bit about this. You came along when southern country customs started, which is, you know, Rusty and Steve's motorcycle company. Steve runs it all over there with, with Josh. And they've learned so much, so much. Now to where the industry, the, the complete motorcycle industry, they really admire Stephen and Rusty and Josh. They have learned so much about the ride and the balance. We've watched it just get to the behemoth, how balanced it is. And I love the service. If something's wrong, Rusty's like, Rusty learned that from Roger. Service, service and service. Yeah. Anything wrong, they're going to make you right.
Jamie Flannery
That's right. And they, you know, one of the biggest things I talked to Steve about, I said, Steve, it's a different kind of buyer that buys your bikes.
Kenny Wallace
Yeah.
Jamie Flannery
I said, I said, to be honest with you, I said I don't even want to air the tires up on my bike, bring them to you and Josh in a service trailer and I want you to do everything for me because I don't want to do any of it. But, but I want my stuff. Right? I'm willing to pay you to do it. I said, and I said, so are the rest of your bike riders, the people that own these bikes? I said they're, they're high end bikes and they're expensive and they're beautiful. So Steven, you know, and I wouldn't say it's all my idea, but you know, Rusty probably knew he had to have a service trailer to service all these bikes. I think they've built 160 of them now or whatever they're up to. So there's, there's quite a few of these things floating around. And you know, I, I talked to Steve a little bit this spring about helping him move Southern Country Customs to Daytona. And I said, Steve, this is the, I said Rusty's got a house here, I got a house here and I want to help you get Southern Country Customs where it needs to be. And I said it needs to be here. This is, it's, it Sturgis is, is a one time thing, but Daytona is a year round thing. We got the largest Harley dealership in the world and we need to position your shop close somewhere next to the, the biggest Harley dealership in the world. And, and it's Bike Week. Happens twice a year. That gives, that gives you two events that you don't have to leave home on. You can, you know, you know, ride, sell bikes out of here year round. And, and I said, you vote. I went to his shop and visited his shop and he's outgrown his shop. Yeah, he needs, he needs to, we need to help him find a new shop and put in a new powder coat thing and, and whatever he thinks needs to be done. And I said the first thing we're going to do is we're going to sink them your lifts into the concrete in the floor. I said, so the whole floor is flat and you don't drive up on these things. And I said I got some ideas to help help you. And I said I want to, I want to help you build a shop. Whatever it takes to build it. I said we're just going to do it. And he thought it was a great idea. We got to run it by the Colonel, Rusty first before we do anything or we do nothing. Right. So everything's got to be approved by him first because he's all of our bosses in the bike riding world.
Kenny Wallace
So you know, I got to give my 2 cents on this I came up for air one day and I'm like, what the hell is Rusty doing? He's got a house in Cabo, sleeps 22 people. Started, started a motorcycle company and I'm like, you know, Rusty's really private nowadays. Now, years ago when he was in nascar, us, us Wallaces, we, we will talk. And we're wired tight. We know that. But boy, Rusty is really relaxing nowadays. And he loves this motorcycle life because it's kind of like Kyle Petty said, Cal said. You know, I used to think it was about the motorcycles, but it's about the people. And, and I think when you and all of us get together, we're just excited to see each other. And then the motorcycles do tie us together. Do, do you feel that camaraderie? I mean, yeah, the motorcycles are there, but we get to see each other.
Jamie Flannery
That's, that's the best part about going to Sturgis. Rusty sets up this tent. We get to eat together every night. Yeah, and that's, that's my favorite part. The, the Sturgis is just a reason and the bike riding is just a reason to go to that location to get us all together. But that's not the important part. The important part is when we're drinking a beer at a little bar we stop at or we are cooking out and Tuna is fixing us up the best food ever in, in our campground. And we all get to camp together and it's, that's my favorite part of it. And doing the charity ride. And I don't think we quite hit 500,000 last year, but I think we're going to get there this year. So we'll, we'll hopefully get Rusty's charity right up to 500 grand. That was Angie Skinner's goal last year. But they, they got in the four somewhere, so we're close.
Kenny Wallace
You read my mind, Jamie. Rusty's Ride, August 14, I believe it is. Let me check my calendar. Everybody here, Rusty's Ride. This is. Yes, my big brother. That is such a badass. He has a wonderful heart. August 15th. It is Saturday. August 15th. I believe that's what it is. And it's called Rusty's Ride. Check it out right now. Go to Google Rusty's ride dot com. You know, and we start in Deadwood, South Dakota. We go a one hour ride through Spearfish Canyon. The money goes to the NASCAR foundation and of course the Special Olympics out there around Spearfish. Actually, everything starts on Wednesday. It's a big old weekend. Wednesday night is dinner. Then we'll have Dinner again on Friday night. Then Saturday around three. It is a damn good time. So check it out. Rusty gives 100% of the money away. NASCAR's out there, they appreciate Rusty. The mayor is out there. Everybody at Sturgis gets involved in Rusty's ride. Hey, Jamie. It is. Let's brag on Rusty for a minute. Two more minutes. I'll let you go, my friend. But it is a lot of fun to watch the people of Sturgis and Deadwood acknowledge big brother Rusty. Rusty's got enough money. He don't need any money. He's got 11 dealerships in Knoxville, Tennessee. He loves giving money away because it brings the people together. Just speak to that.
Jamie Flannery
He. Yes, he does. You know, which, it's awesome what he does out there. And Rusty is a huge celebrity and he, he adds, he adds so much to him just himself being there, let alone the charity ride that he puts on. And it's, it's, it's a great event. And the one thing I will say about it is that you don't need one of his bikes to come ride. Yeah, his charity event. You bring, bring whatever bike you got and come help us raise some money and get us over the 500 grand mark this year.
Kenny Wallace
Yeah. And it's a big time, everybody. Okay, there he is, everyone. The great Jamie Flannery. Jamie, thank you so much. I know you pulled on the side of the road for me to do this. It means the world to me. Charlie will get this all edited up. We'll make you look good, buddy. We're gonna drop some pictures of your off road truck in there, you know, your storm trucks and everything you do. So if you. Anything else, my friend?
Jamie Flannery
No, that's, that's a, that's the life story of me, pretty much. And, and what I'm doing today and plan to go to Sturgis and keep riding bikes with you guys and having fun. You know, like I say, we're, we're on the back nine. We gotta enjoy it.
Kenny Wallace
That's right. Oh, there's some. That, that's a whole nother story. Okay, everybody, listen up. If you want to see Jamie Flannery's pretty face, tune into the Kenny Wallace YouTube show. You're going to see us if you want to listen. And you're on your way out to Sturgis. Turn into Dirty Mo Media podcast. Dale Earnhardt junior's podcast over there. Until the next Kenny conversation. Goodbye, everybody. Check out Dirt Dirtymo Media on Twitter, Facebook, TikTok and Instagram.
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Jamie Flannery
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Episode: Jamey Flannery: Appreciating A New Lease On Life
Date: June 4, 2026
Hosts: Kenny Wallace (with regular presence of Ken Schrader)
Guest: Jamey Flannery
Duration: Approximately 64 minutes (excluding ads and outros)
This episode of Herm & Schrader centers around Jamey Flannery, a legendary off-road racer, businessman, and a beloved figure in the Wisconsin racing community. Host Kenny Wallace delves into Jamey’s dramatic recent health scare and recovery, his upbringing in the world of off-road racing, his business ventures, and the unique lifestyle and camaraderie formed through racing—and, lately, motorcycling. The conversation is heartfelt, candid, often humorous, and celebrates both Flannery's resilience and the communities that shaped him.
[03:25–08:11]
[08:30–12:49]
[13:51–20:02]
[20:31–24:57]
[24:58–30:01]
[38:46–44:39]
[48:45–51:13]
[52:59–59:23]
[60:19–63:48]
Surviving Cardiac Arrest:
On Walker Evans’ Grit:
On Equipment and Cleanliness:
Race Track Legacy:
On Motorcycles & Community:
This episode captures the raw authenticity and irreverent humor that are Herm & Schrader’s trademarks—ranging from emotional examinations of mortality and legacy to the simple joys of racing, working, and riding motorcycles with friends. Jamey Flannery emerges as a humble but determined figure shaped by family, racing, and business—dedicated to doing things right, giving back, and celebrating the journey at every turn.