in: Character, Knowledge of Men, Podcast

• Last updated: May 6, 2024

Podcast #985: The Secret World of Bare-Knuckle Boxing

Have you ever noticed the guy in a fighting stance on the Art of Manliness logo? That’s not just some random symbol; it’s an actual dude: John L. Sullivan, the greatest bare-knuckle boxer of the 19th century.

While most people think bare-knuckle boxing came to an end during Sullivan’s era, in fact, it never entirely went away. In his new book, Bare Knuckle: Bobby Gunn, 73–0 Undefeated. A Dad. A Dream. A Fight Like You’ve Never Seen, Stayton Bonner charts bare-knuckle boxing’s rise, fall, and resurgence, as well as the improbable story of its modern chapter’s winningest champion. Today on the show, Stayton describes bare-knuckle boxing’s incredible popularity a century ago, and why gloved boxing took its place while bare-knuckle got pushed into a shadowy, illicit underground. Stayton takes us into that secret circuit which still exists today, revealing the dark, sweaty basements and bars where modern bare-knuckle fights take place and the ancient code of honor that structures them. And Stayton introduces us to a dominant figure in that world, Bobby Gunn, an undefeated bare-knuckle fighter who combines a love of faith, family, and fighting and has helped turn bare-knuckle boxing into what is now the world’s fastest-growing combat sport.

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Read the Transcript

Brett McKay: Brett McKay here. And welcome to another edition of the Art of Manliness Podcast. Have you ever noticed the guy in a fighting stance on the Art of Manliness logo? That’s not just some random symbol, it’s an actual dude. John L. Sullivan, the greatest bare knuckle boxer of the 19th century. While most people think bare knuckle boxing came to an end during Sullivan’s era, in fact, it never entirely went away. In his new book, Bare Knuckle, Stayton Bonner charts bare knuckle boxing’s rise, fall, and resurgence, as well as the improbable story of its modern chapter’s winningest champion. Today in the show, Stayton describes bare knuckle boxing’s incredible popularity a century ago and why glove boxing took its place while bare knuckle got pushed into this shadowy, illicit underground. Stayton takes us into that secret circuit which still exists today, revealing the dark, sweaty basements and bars where modern bare knuckle fights take place and the ancient code of honor that structures them. And Stayton introduces us to a dominant figure in that world, Bobby Gunn, an undefeated bare knuckle fighter who combines a love of faith, family, and fighting and has helped turn bare knuckle boxing to what is now the world’s fastest growing combat sport. After the show’s over, check out our show notes at

All right, Stayton Bonner, welcome to the show.

Stayton Bonner: Thanks for having me. Thrilled to be here.

Brett McKay: So you got a new book out called Bare Knuckle: Bobby Gunn, 73-0 Undefeated. A Dad. A Dream. A Fight Like You’ve Never Seen. And this is a book about a bare knuckle boxer in the 21st century named Bobby Gunn. You spent several years of your life following this guy to get a look at what his life is like. When did you first learn about Bobby Gunn and what drew you to this story?

Stayton Bonner: Yeah, as a journalist, I have to tell you, it’s one of the most inspiring and heartbreaking stories I’ve ever come across. It’s a real life Rocky story. Ultimate underdog tale. Bobby Gunn, I first saw a blurb about him in 2011. He was a fighter in the first bare knuckle boxing match in the United States in 120 years. It was held on an Indian reservation in Arizona.

Brett McKay: This is the first sanctioned bare knuckle boxing.

Stayton Bonner: Yeah, it was sanctioned outside of a state boxing association commission. It was actually a tribe that was able to do it. So he won that. It got a little bit of attention. I was working as a magazine editor and writer at GQ in New York at the time and looked him up. He was across the river in New Jersey and went and met him. And it was amazing. He had overcome an abusive childhood. His father was having him fight grown men in parking lots when he was 11 years old, basically waking him up in the middle of the night to fight guys he’d bring home from the bar to win cash. And he had a great run as a professional boxer and then gotten into this underground, illegal world of bare knuckle boxing to make money so he could put his seven year old daughter through private school. That story alone just, it was fascinating that he was able to rise from that abusive childhood to become a champion. And everything he did, he always thought of his daughter right before he stepped in the ring. And that just really resonated with me.

Brett McKay: What I love about this book is that you used Gunn to explore a culture that you didn’t think existed anymore. And it’s a culture that goes back to the 19th century. I mean, you can even say it goes back even further. I mean, this can say it goes back to Odysseus. Like these guys Bobby Gunn and these other underground boxers, they’ve got more in common with Achilles and Odysseus than they do with us. And I want to talk about this culture today because I think it’s just really fascinating. People might be surprised to hear that bare knuckle boxing still exists in the 21st century. And to understand the state of the sport today, I think you’ve got to do a little bit of history. So take us back to the beginning of bare knuckle boxing in the United States. What were those first matches like?

Stayton Bonner: Yeah, bare knuckle boxing. It’ll surprise people. It was one of the most popular sports in the United States in the 1800s, that’s bare knuckle boxing, horse racing, and baseball. Those three sports garnered the most attention, the most headlines. As you would imagine, the rules sound exactly like what they are. It’s stand up boxing. No grappling usually, and just without gloves or they had very light gloves on. And it was always a means for people, typically immigrants, people in dire situations to raise themselves up in society.

In the book Bare Knuckle, we recount a story of Tom Molyneux, who was an enslaved person in Virginia, became renowned fighting on plantation bouts, won so much money that his master freed him, and he then made his way to be a dock worker in New York City, got on a boat, traveled to England, fought a British champion overseas, made headlines overseas. Another example is from the film, Gangs of New York, the Martin Scorsese film, the Daniel Day-Lewis character, Bill The Butcher, they do depict a bare knuckle fight in that movie. Bill The Butcher himself was a renowned bare knuckle boxer.

And he and a lot of other Irish immigrants were able to translate that fame in the bare knuckle ring to political power. Definitely the most famous example of a bare knuckle fighter in the 1800s. He was the LeBron of his day. And also the logo of Art of Manliness podcast was John L. Sullivan. He was the son of an Irish immigrant, a plumber.

As a teenager, he was working with his dad and working on scalding pipes in Boston. Saw an invite to come in and challenge a famed boxer. On a whim, took off his coat, put on these thin gloves and knocked the guy out. And then he left the world of plumbing behind and became extremely famous. There were songs written about him. He was on a traveling circuit.

He would wake up, eat a dozen raw oysters every morning, drink some whiskey and basically go town to town and would invite anyone to come in and try to beat him. Nobody could. It culminated in the most famous fight of the 1800s, the most famous bare knuckle fight, which was him against Jake Kilrain. He was a Boston millworker. And that had a really interesting backstory because Sullivan had actually inadvertently insulted the publisher of the National Police Gazette, Richard Fox, very popular newspaper at the time. Sullivan was dining at a restaurant in New York City.

Fox, the publisher, a very powerful man, saw Sullivan, who was known as the Boston Strong Boy, invited him to his table. Sullivan said no, the publisher should walk to him. And that petty encounter led to a years long feud. So Richard K. Fox basically put the money up for Jake Kilrain to fight John L. Sullivan. And it became a duel of newspapers because if a rival newspaper got behind Sullivan, they would each depict weekly updates on these guys training and Kilrain doing things like training while cradling babies. They showed Sullivan abusing dogs, drinking at Daverns. It ended up the two of them met in 1889 and they did a fight in front of 5000 fans. Legendary gunslinger Bat Masterson was there. I think it’s important to note that this was still illegal. I mean, because it was gambling.

It varied state to state, but the newspapers still covered it. But it was done undercover. There was a special train in New Orleans where the fighters got on and the fans in the early morning took them to a secret location, this lumber farm in Mississippi. And it was an epic fight between these two guys. Again, this was covered around the world in newspapers. It was two hours, 76 rounds they had spiked cleats on. This one was going a bit beyond just the simple boxing rules. They were stepping on each other. And it was a $20,000 purse, which was in addition to a $1000 side bet between the two men, which is, which is a huge amount of money. And John L. Sullivan knocked him out and became famous.

What’s interesting is his opponent, Jay Kilrain, was actually the great great grandfather of Colin Kilrain, who ended up becoming head of… Who’s a Navy SEAL and head of NATO special operations command. And it’s funny that admiral would cite that fight in his family lineage, but John L. Sullivan then kind of went underground in terms of his drink and his health after that and kind of following his disillusion personally, bare knuckle also went underground.

Marquess of Queensberry Rules came up. Gloved boxing overtook bare knuckle as the preeminent sport, and it all went into the illegal circuit where it stayed for 100 years.

Brett McKay: Okay, so, yeah, bare knuckle boxing, it was the thing, it was so big in the 19th century, they called it the manly arts. And yeah, John L. Sullivan was just, he was like the first mega celebrity in the world. I think people really don’t appreciate how big the sport was. And as you said, the fights were different back then. Like you said, that fight with John L. Sullivan and Jake Kilrain, it lasted 76 rounds. And it wasn’t the set timed rounds we have today. I mean, these guys would fight a little bit and then they take a break and these could go on for hours.

Stayton Bonner: Absolutely. And it’s quite different from the bare knuckle fights I personally witnessed, which are usually very, very fast now. But back then, I mean, look, they would just create a makeshift ring. It was till the other guy basically got knocked out or just couldn’t stand up anymore and his team threw in the towel. But they would just go at each other, bleeding all over the place, go back to the side, drink some whiskey, get a pep talk and head back out there. It was lawless.

Brett McKay: And the sport, as you said, it attracted a lot of people from the lower classes and typically were immigrants. So a lot of Irish Americans. John L. Sullivan, his parents were Irish immigrants. If you saw the movie, you mentioned Gangs of New York, Irish immigrants. There’s bare knuckle boxing, another movie that features Irish immigrants Bare knuckle boxing. Remember that movie Far and Away with Tom Cruise.

Stayton Bonner: Yep, absolutely.

Brett McKay: Yeah. What happened in America that caused glove boxing to take precedence? Was this an attempt to make boxing more legitimate?

Stayton Bonner: Absolutely. It was already coming up, and there were kind of the dueling arts. They are different sports, different sciences, but essentially bare knuckle boxing. It’s skin on skin. It looks bad. It gets bloody very quickly. What’s funny is the science behind it. So it’s just like the difference between watching a rugby game and watching American NFL. Rugby, no helmets, very little padding. These guys are getting bloodied up very quickly, but they’re not hitting each other as hard as they would if they were totally wearing helmets and thick pads, simply because they don’t want to break their bones or hurt themselves too much. If you think about an NFL game we’ll watch on a Sunday afternoon, your kids can watch it. You’re not seeing the violence, you’re not seeing the deep impact, but they’re hitting each other ten times as hard as a rugby player. That’s the same difference between boxing and bare knuckle boxing.

Fighters pull their punches inherently just ’cause they don’t want to break their hands on someone else’s bones. But it looks more bloody because it’s skin on skin, and it’s a lot of superficial blood and cuts. Neither one of these sports are obviously, “safe.” But bare knuckle boxing, according to preliminary studies, does result in less concussions.

In the 1800s, bare knuckle boxing was on its way out in terms of a rise in religion and being upright in society. And the guys think this thing’s just too brutal. They were also trying to tamp down on gambling. It’s always been a heavy gambling sport. And so boxing it looked cleaner, it looked better. It was a little bit better product, I think, to sell to a wider audience. And that’s why it rose up and bare knuckle receded into the shadows.

Brett McKay: Yeah. During that time, the late 1800s, you saw the professionalization of sports. Boxing, baseball, football. There is these movements. I think you probably attribute it to the progressive movement as well. If we’re going to try to make things safer, more bureaucratic, more efficient, we’re going to apply principles of industrial management to sport, which, yeah, as you said, we can make it just safer when people can feel better about taking part or watching them.

Stayton Bonner: Yeah, absolutely. It’s funny, though, you got to keep in mind I spoke with one state boxing commissioner and he pointed out to me the boxing and fight world in general, it’s a billion dollar sport run like a five and dime store. There’s no NFL, there’s no MLB, there’s no NBA. There’s no national sanctioning body of the sport of boxing. It is still run essentially like it was 200 years ago, which is basically by each state. You have these state boxing commissions. They get to decide what the rules are, what is allowed, what is not.

Obviously, there’s a broader coalition of these groups that have influenced nationally, but it’s very different. I mean, it is still run basically by these state fiefdoms. It’s an unusual sport to this day because states can basically dictate how they want to operate it.

Brett McKay: Okay, so glove boxing took precedence during the 20th century. And then bare knuckle boxing, it never went away, it just went back to the underground. It went really underground. People just stopped talking about it. Who organized these bare knuckle matches throughout the 20th and 21st centuries?

Stayton Bonner: Yeah, I mean, it was fascinating. This was a secret world, totally underground. I mean, really underground, if you think about it before cell phones and internet. But it was basically run by organized crime. So it’s not really that different from… This varies by region. It’s a blood sport. So you can think of dog fighting, you can think of cockfighting, you can think of pitting grown men against each other. And it was all run usually by local organizers. A lot of it was in New York City was the epicenter, but basically with Bobby Gunn, he was backed by the Irish mob.

So they would basically stake him in New York in fights along the east coast and pit him against fighters from rival organized criminal groups to where he would go to Chinatown and fight someone that that group had brought in. He’d go to Sheepshead Bay and fight someone that the Russian mob had brought in. He’d go to Boston and fight someone the Latin kings had brought in. So it was always… That would vary. Situation, situation. Motorcycle gangs would hold bouts. But basically these were matches where Bobby Gunn didn’t have $10,000 to put up in a match. He would be staked by organized crime, and then he would go to his buddies and gather money for a purse, put in a little bit of his own, and everybody would put in their cash.

The day of a fight, they would give their stake money, just a big wad of loose bills to the house. And I talked with one promoter of these, and he would carry around a contraption he called the cage, which was a portable metal safe with holes drilled into its lining. He’d go to a venue, open the safe, screw it onto joists in a wall, or shoot it with bolts in a concrete floor, put the prize money in and close it up.

But it was funny, he said, it’s you would think that these might be prime targets with all this loose money for being robbed, but everybody was packing heat at these things, and no one’s going to come in and stick each other up. So they were kind of these honor systems, kind of these Switzerland type encounters where organized criminals could come together and have fun on a underground prize fight match in a truce like state and pit their fighters against their… And that’s how Bobby Gunn came to rise to prominence.

Brett McKay: What are the rules of these modern day bare knuckle bouts?

Stayton Bonner: Yeah. So typically with bare knuckle boxing, it’s going to be just stand up boxing rules applied to a gloveless match. So there’s no hitting below the belt, no grappling, no getting someone to the ground, no kicking, no gouging of eyes, that kind of thing. There are fights, though, and this is typically established up front, where it’s called rough and tumble. And rough and tumble means all rules are off. It’s like I have no respect for you. I’m going to do anything it takes to take you down, whether that’s ripping off your ball sack, literally gouging out your eye, biting off an ear, all of these kind of things. It’s just a… It’s literally a lawless situation. Now, those are rare, but Bobby Gunn has fought in those.

Sometimes these fights will devolve into that, I think pretty rarely that’ll be the setup going into one, and we can talk more about that later. But in general, these are run as straightforward boxing matches without gloves, and they’re just bloodier, and it’s a faster situation.

In the 1800s, of course, these things would go for much longer. These days, it’s not about putting on a show as much. These fighters want to get in and out. Bobby Gunn was never that worried going into the ring against an opponent, but these situations were dangerous. He had guns pulled on him multiple times. He wanted to win the money quickly and get out, so he would really focus his shot and try to take someone out as quickly as possible, take his bag of cash and go.

Brett McKay: And you had to make it fast, too, because you’re always concerned about the police showing up, and so you had to get out of there as quickly as possible if that’s did happen.

Stayton Bonner: Absolutely. Fighters would often… You’re not going in wearing a cape and your boxing trunks and shoes. Bobby always wore jeans, sneakers, black T-shirt. That was how he rolled because he would usually come in off of working asphalt to do these things. But also that was so if the cops did come, which I recount stories of cops coming, everybody runs, and you don’t want to be the guy who was clearly the guy in the ring fighting. And I say ring. I mean, look, sometimes there are makeshift rings. Oftentimes these are held… I’ve been to fights in an auto body shop in the middle of the day. They just close shop, and everyone knows to come in the back and do this while they’re fighting around oil puddles and cars up on jacks, they fought in the back of gyms, in the Hells’ kitchen.

He’d go through an Irish bar that was owned by the Irish mafia, through a back door, down into a basement, and that would have been a fight arena. Sometimes it’s in a parking garage, so it’s not like there’s a ring. And these things come together very quickly, very late, and you just got to be in the know to get the invite.

Brett McKay: What was it like being at these fights? Was it… I imagine. ‘Cause I remember when I was in high school, you’d go… There’d be these fights, kind of makeshift fights. Meet me after school at this park. You’d be circling around. It was kind of as a bare knuckle bout. And I remember being at these things. I always kind of felt like this is kind of illicit. I probably shouldn’t be here, but at the same time, it was really… It was kind of exciting. Like, the hairs on your neck would stand up, and you’re just watching these guys just wallop each other. Did that happen to you when you went to these things?

Stayton Bonner: 100%. One person, I remember one of the first fights I went to, they were like this shit is cool, because it’s illegal. So it was always, frankly, exciting. I mean, one of the first fights, I was working as an editor, writer at Conde Nast. I get a text on my phone. This was, I don’t know, 2013. There’s a fight happening in a few hours. I got on a train. I went to the location. I was then texted the address. I went to the address, and it was in the back of a gym, and it was raining, and out walks Bobby Gunn with a T-shirt, and he’s holding a baseball bat just for security. Another person, David Feldman, who now runs the bare knuckle fighting championship, basically came up behind me and said, if you put my name on this, you won’t write again.

It was, frankly, kind of scary. But I will say you go in, and it’s a small group of people, and it’s kind of hot, it’s kind of sweaty, and these I think that that fight, it was a Hells Angel versus a former marine. It was one of the bouts. And these guys got into it pretty quickly. The thing that hits you is the sound. There’s nothing that resonates or makes it clear. This is a totally different animal from all fighting I’ve ever seen, is the sound of skin on skin. This is kind of a wet slap, and you just kind of feel it, and you immediately see the blood and its guys just moving around kind of in a shadowy arena with people literally surrounding them, holding up money and yelling. And it was an adrenaline hit, for sure.

Brett McKay: No, for sure. We interviewed John Gottschall a long time ago. He wrote a book called why Men fight and why we like to watch. And, yeah, he just talks about, like, even though we are in the 21st century and us who live in the suburbs of the city were like, oh, I’m sophisticated, I’m above that, there’s still something inside of us that is drawn to that. It’s exciting. We’re going to take a quick break for a word from our sponsors. And now back to the show.

Okay, so let’s talk about Bobby Gunn. So this guy was born to be a bare knuckle boxer because he was born into a family that belonged to an ethnic group called the Irish Travelers. Tell us about the Irish travelers.

Stayton Bonner: Yeah, the Irish travelers. If you’ve seen the guy Ritchie film Snatch, the Brad Pitt character, that’s an Irish traveler. These are a group of people who were basically ostracized from traditional society in Ireland in the 1718 hundreds and were wanderers, were nomads. They would go town to town, do odd jobs, live on the outskirts of a village and they were ostracized it was kind of a love hate relationship. People in the town might need them as day labor but they didn’t really want them to assimilate. They were always outsiders.

In their culture, they revered two things, which was religion and fighting. So I interviewed John Steigals who was a priest in Memphis, catholic priest who worked closely with the traveler society there, and they’re very closed off. They typically don’t allow people in. There’s maybe an estimate of 10,000 of these people living in the United States. But he gave me some insight on their religious outlook and it’s very rooted in Old Testament approach, almost like a mystical Christian outlook that involves some druidism, aspects from the old Irish lore. And Bobby Gunn would talk about this. He would recount stories of waking up to see an evil spirit in hard times of his life. He’s always thinking about the devil. He is extremely religious, would lie prostrate on the ground before fights, was not a drinker, smoker, no tattoos, did everything for his family.

But these people revered fighting and it was an Old Testament eye for an eye outlook and Bobby Gunn would say, Jesus was a banger. That guy had to take down a temple, the money counters. He wasn’t some skinny wimpy guy. Jesus was a fighter. Like that was his outlook on religion and fighting and fighting as you would imagine for these people who are ostracized and marginalized Irish travelers. He makes his living going basically door to door trying to do asphalt work, left school at third grade, so basically has had no education, which is why it’s so important for him to put his daughter through school so he can give her a better life.

But he just literally has had to fight for everything in his life. And that’s pretty typical of the traveler community in general.

Brett McKay: And these travelers, the fighting, not only did they make money with the bare knuckle fighting, but fighting for them was a way they could gain a reputation, gain status, gain honor. Like it actually had stakes for their identity.

Stayton Bonner: Absolutely. So if you… I mean it’s very rare for travelers to have too much material wealth, given their lifestyle and everything. So as you point out, your ability to fight is truly a reflection, as Gunn would put it, his bloodline, his heritage. It’s an oral history community. Stories are passed down from each other, generation to generation. And in the book, I write about how he recounts the exploits of his great great grandfather, who had come over and gained renown as a fighter.

He talks about how he fights now for his family. There’s a particularly poignant scene where there is someone, another traveler, who is bothering Gunn and bothering his family. And Bobby makes it a point to go to this man’s dinner table in his camper at night and calls him out in front of his family. And he does this because he knows the man will not fight him. And he just shames him right there. And like that alone, Bobby Gunn walks out.

But the man has been shamed and basically shunned from the community in a sense, because everyone now knows he backed down from a fight. And that’s like the lowest, toughest thing Bobby could do to the man because it’s going to destroy his reputation. So fighting is inherent to the Irish travelers in terms of their identity and their self honor and their honor as a family. And that’s also what Bobby grew up being trained to fight for.

Brett McKay: Yeah, and going back to this idea of the connection between fighting and religion, the way you described it, I kept on imagining. I kept on going back to gangs of New York. If people seen that movie, they’ve probably seen that opening scene where there’s the battle and it’s like that perfect combination of this druidism and Catholicism and fighting all combined into one. And when you watch it, you’re thinking, man, this is like something out of, I’m reading a Greek epic here. This is not even the 19th century. I mean, this goes even further back. And I kind of feel like Bobby Gunn and these Irish travelers, they still have that mentality.

Stayton Bonner: They absolutely do. I mean, they’re like modern day Spartan warriors that’s what Bobby Gunn’s son, he would talk about the film 300 and that he related to that because the children are typically pulled out of school by middle school. They don’t want them to assimilate with broader culture. And their culture is entirely revolving around the world of fighting, training to fight, and religion. And it’s not… There’s nothing skeptical about it. There is nothing ironic.

I mean, Bobby Gunn devoutly believes in Jesus as his savior and sees absolutely no discrepancy between being a true believer and basically punching, pummeling a man to the ground, tearing out an eyeball if he has to, ripping a cheek open. I interviewed another fighter who said, Bobby Guns is just like anyone, no one I’ve ever met. He’s like this guy would be in the ring telling me how to do dirty moves in a boxing match that the ref won’t catch, how to elbow your opponent in the eye when the ref won’t see it. And then he would afterwards take me aside and ask if I’d allow Jesus into my heart.

So it’s like, that is absolutely that 18th century, 19th century mindset of devout religion, devout purpose, melded with violence and having to fight for everything you have in this world. That is what these guys live still today.

Brett McKay: I mean, speaking of how insular they are, the Irish travelers, they even have their own language. Like, it’s a secret language.

Stayton Bonner: Yeah, it’s called Cant. And the joke is, you can’t understand us. But Bobby Gunn would always be slipping into this secret language with his family. I spent years with him and his family and his friends. I was given unprecedented access into the traveler culture, went to fights, traveled with these guys, and, yeah, they would slip into this language all the time that only they understood and then come back. They also have a very unusual accent. So the film the Dark Knight, Tom Hardy playing Bane, he based that accent, which sounds very placeless, on a famous bare knuckle fighter in England, in Wales. And he did that because it’s just a rootless accent that’s hard to place. It’s very distinct. You’ll talk to travelers. They kind of have an Irish accent sometime. I mean, it’s really wild, and it was unlike any other group of people I’ve ever seen. They totally distrust outsiders, do not let people in, and it was pretty unprecedented to get deeper with them.

Brett McKay: Okay, so the traveler culture fighting is a big part of it. Bare knuckle boxing is a part of that. A lot of famous glove boxers came from the Irish travelers as well. But I want to talk about this. You mentioned this style of fighting that Irish travelers often take part in. It’s the rough and tumble, and this is fighting not for sport. This is fighting for honor. And this is a fight where, as you said, there’s no rules. And you mentioned some of the stuff that went on… That can go on in a rough and tumble. There’s eye gouging, you mentioned, like, you can rip people’s ball sack off. Basically. There’s fish hooking. Did you ever see any of these, these rough and tumbles? And tell us about Bobby’s Gunn’s experience with these things.

Stayton Bonner: So Bobby grew up being trained in three different fight disciplines. Number one was boxing. He was training from, literally when he could walk to be a pro boxer. His dream was always to be an olympic boxer. He was also trained in the art of bare knuckle boxing, which, as I said, is pretty straightforward in terms of boxing rules. You just have to hit your opponent in different spots so you don’t break your hands. You have to be mindful of that. It’s more about body shots, liver shots hitting someone above their eyes to bloody their vision. Kind of take the fight out of them and then take them down with a straight shot to the liver or the heart. That’s a pretty, pretty good move. But the third discipline was rough and tumble. So Gunn’s father, Robert Williamson Gunn, grew up a street fighter.

He was in before the WWE. He was a heel in a traveling wrestling circuit where these guys would go town to town in a van, get out do a show. Of course, they had winners and losers predetermined, but they were beating the hell out of each other, cutting themselves up with razors for the crowd, then going to the bars. He was also a notorious drinker and would go out at night and drink all night and then come back and go out to work. So he raised Gunn from an early age in this dark arts of rough and tumble, which basically is your honor’s on the line, anything goes. Literally, no rules.

So Robert would train Gunn as a young child. He’d rub a leather belt over his eyebrows to toughen them up. He’d pour kerosene on his cuts to heal them more quickly. He wanted to teach him how to take pain. So when Bobby Gunn was a child, his father would wrap a baseball bat with foam and duct tape and hit him repeatedly in the midsection to harden his eyes. I mean, to harden his abs, and that was just something he grew up with. So the rough and tumble aspect is… It’s an abusive childhood, and Gunn will say it sounds crazy, especially since his dad would wake him up to fight grown men in parking lots for cash. But he was always forging him to be the ultimate weapon to survive in these rough and tumble fights. And that’s a lot of times, it’s out of disrespect. It’s called a fair play fight, which is like a typical bare knuckle bout. But if they say rough and tumble, that’s like I think you’re a piece of shit. I think you’re a dog. I want to take you down.

A lot of times, that’s in the moment, so that you could have come up to a fight, and it could have been set this traditional bare knuckle. And your opponent says that. At that point, if you say, no, no, I don’t want to do that, everybody knows you got a little less heart. They know you’re a little scared, so you really don’t want to back down from that. So Gunn was in a lot of those fights. Sometimes, though, it’s just desperation. Bobby would sometimes be beating an opponent. The guy would be on his last leg, and then he would do a dirty move. But, yeah Bobby Gunn, he would tell me many stories. I mean ripping a ball sack off, told about one guy had a ring through his balls. He ripped it out. He’d take a finger, pull out an eyeball. Had an eyeball hanging from a guy’s face during a fight, he’d bite an ear and nose off. It was pretty crazy, sticking a thumb in an eye.

He would describe it, hearing a rip when it comes out, seeing a man squeal and dropped to the ground. And Bobby Gunn will just say this stuff pretty matter of fact, just after he’s dropped his seven year old daughter off at the private school she attends. And he’s like, yeah, this makes me sound like an animal, but someone was trying to do it to me. And you just got to remember that. Bobby was a very gentle soul. He is. And it was interesting and poignant because he would tell me his greatest fear was not these dire situations where it was the bloodiest battle you could imagine. It was when he dropped his daughter off at her school every morning, and he always worried that her friends or her friend’s parents would know who he is. And know the things he’s done and that would somehow ostracize or hurt his daughter. That was what he constantly thought about. He was just… He purposely did not bring up his… He has a son. He purposely did not bring him up in the art of rough and tumble or bare knuckle, because he just didn’t want him to enter this world. But for Bobby, that’s what he was raised in.

Brett McKay: Yeah, we did a podcast back in 2013 with a professor of history, Dr. Lorien Foote. She wrote a book called the Gentleman in the Roughs, and it’s about honor culture in the American north during the civil war. And she talked about how the officers, they followed this sort of traditional honor code very gentlemanly. If you had a dispute with somebody, you’d follow the rules of dueling. It was like this very drawn out process with all these formal rules. But the infantrymen, who were often Irish immigrants, they used rough and tumbles to settle scores of honor. I mean, she talks about that, too. So this is like a tradition that goes way back, particularly in Irish immigrant culture.

Stayton Bonner: Yeah, there was just briefly to speak on the honor aspect. There was one story which was insane, which was a fighter. I had to use a pseudonym, but he was working as a prison guard in the 1990s at a maximum security state prison along the mexican border. And this is to the idea of bare knuckle fighting as honor. There was one guy in the yard who was constantly giving this guy, who was the security guard in the prison, and it was a person within the Mexican mafia there. And he had come up as a fighter, this prison guard. He kind of knew the rules. He basically told me it’s not the guards that run the prison, it’s the inmates, and you gotta save face.

So one day, he basically handed a note to the person who was tormenting him and making fun of him all the time because he couldn’t do anything in public about it, saying he wanted to fight him. So they set up a fight that night. The prison guard brought one other prison guard. He also brought two members of the Aryan Brotherhood. This is a white guy. And it was two members of the Mexican mafia who came to watch him. And they got in a deep freeze vegetable room in the commissary, which basically a concrete floored, windowless cage with crates of produce around them. They stripped to their pants. This is a prison guard. And a prisoner stripped to their pants, walked into this, clinged the shut door behind them, and went to fighting. And it was going on for a while and kind of the secondaries were watching standing guard. And at one point, the prisoner who had been tormenting this prison guard pulled a shank, pulled a knife, and stabbed him in the leg. He dropped. But then at that point, it was actually that prisoner’s own people, the Mexican mafia, who ran in and pulled him out of them and started beating the hell out of the prisoner. And they said, we’re done. We’re sorry that happened. And it’s because that person pulled a weapon.

It was supposed to be a fair underground fight because he had violated the honor of the entire premise. It was actually their own man who was beated so badly that showed disrespect on his people. They had to ultimately transfer that prisoner away because they were worried about his life. And that prison guard after that never had any other trouble with any other inmates because he said they knew I was a stand up guy. But that’s… I mean, it’s just an insane story of a prison guard knowing we have to settle this dispute as men with a prisoner, and they do it in a produce freezer. And that just underscores the honor aspect of this. It’s all about in this kind of world, do you do what you say? Do you stand up for what you believe in and who’s going to win at the end of the day?

Brett McKay: Yeah, it’s Homeric.

Stayton Bonner: It really is.

Brett McKay: So you mentioned Bobby Gunn trained to fight since he was a kid. He was fighting grown men when he was 11 years old. His dad was toughening him up with leather belts and kerosene and hitting him with a baseball bat. But he was trained not just in the rough and tumble and the bare knuckle, but he was trained to be a legitimate gloved boxer. And he had a… He looked like he had a good career going for himself when he was a young man. What was his boxing career like?

Stayton Bonner: Yeah, absolutely. Bobby Gunn is 73 and 0 in the bare knuckle circuit, a living legend, because of his boxing career. A lot of times you’d have bouncers, you could see the movie Roadhouse, you’d have ex-football guys, you’d have military soldiers. People who were tough and know how to throw a punch, but not with the science behind it. So Bobby came up, literally from childhood, fighting in pro boxing. He fought in Las Vegas, trained under Carl King, who was Don King’s son. But he never got his due in pro boxing. He was always kind of the punching bag, the sparring guy, was put in some bouts, but never really got the shot he wanted. At 30 years old, his mother died, and that really broke Bobby’s heart. And he’d had a hard time in the pro boxing circuit until then, and so he married and dropped from pro boxing at 30, and then was living in the Miami area and got invited to fight basically in an empty concrete apartment complex that hadn’t been finished, a construction site, on the beach that they were holding bare knuckle fights in at night. The surf roaring out there, the wind coming through, and he had just started dropping guys and getting cash. And secretly while he was married, his wife didn’t know this. She thought he had left the fight game, was taking on these bare knuckle fights on the side for money. And that really started to expand his reputation.

But it was because he had the discipline from the boxing world, because he knew how to roll with a punch, because he knew exactly… He’s like a surgeon when he’s sizing you up. And he’s, again, gonna take you out in a way you can easily break your hand on a man’s head. But if you hit them in certain spots, if you get them bleeding, cut their eyebrows, get blood in their eyes, and then go in with a straight shot to the heart, straight shot to the spleen, it just… One guy says, “It made my ass feel like my ass fell out.” [chuckle] It was like… It just drops you. And what was amazing though is for 10 years, Bobby Gunn built up this underground fame. There was a boxing gym where he would train in New Jersey, where they moved to Jersey, and it had a big landline phone in it. I went to it. Ike & Randy’s gym in Patterson, New Jersey. You had to go through chain link fence and barking pit bulls to get to it. And people would call and they would leave a note for Bobby, “Yo Gunn, call this number,” and it would be the mobsters, it would be different criminal groups. And they would leave a number for him to call, and then that would set up a match. And Bobby got so much notoriety from that. At age 40, he had a son, and he wanted to show his son that he could still make it as a pro boxer, that he wasn’t just this underground thing. And that’s when he got back into the pro boxing ring.

So how crazy is that? He leaves it at 30, spends 10 years in the underground bare knuckle boxing illegally, becoming this legend, and then uses that fame to basically return to the pro boxing arena. He fought huge opponents, Thomasz Adamek, Roy Jones Jr. All of these guys respected and knew about his prowess in the underground. He was kind of an oddity, but they were like, “This guy’s a tough guy. This guy’s a standup guy.” He went to go fight Thomasz Adamek at a stadium in New Jersey. Adamek has a ring of people around him, handlers. Bobby Gunn literally drove up in his pickup truck, had paint and asphalt on his clothes, no secondary nothing. He just walked into the arena, put on some boxing trunks, and went up in front of this guy, in front of thousands of fans. That’s what he would do. And he never… He wasn’t a champion, a welterweight… It was never the pro boxing career he envisioned for himself, but he did have a very successful run. But ultimately it was his prowess in the underground that’s made him famous.

Brett McKay: And some of these underground matches that he was in were crazy. Like there was one match, it was organized by organized crime. So I think it was the one with the Russian mafia. He shows up and there’s all these people in nice clothes and there’s a mountain lion in a cage. And people were just there to watch this guy fight. And he was fighting with this mountain lion roaring at him. He said it was really, really weird.

Stayton Bonner: Yeah. Look, Gunn never liked this stuff. And for him again, he was always, always nervous as you would imagine, just about the atmosphere of these things. So that was actually a fight in a suburban mansion outside Boston that was put on by a faction of the Irish mob. And he got there and there was a caged mountain lion in the corner. They did have a makeshift ring in this big backyard set up on this estate. And it was different mobs that have brought in their different fighters. Gunn beat his opponent. He was waiting to get cash. And then a fight broke out in the crowd and gunshots were fired. He got his money and left immediately. The Russian mob’s story is probably his biggest payday in an underground fight. That was in outer Brooklyn, Sheepshead Bay, where there was a fight at the Russian mob at a mansion. There, Gunn and several people I interviewed who went with him, he brought a team of his people, described it as there was an elegant party underway, men and women in evening wear, live music. But then again he was the main attraction of the evening. And they had actually… For that fight, he said two Russians came to meet him at a Starbucks in New Jersey to discuss the fight to set the money. He’s like, “They were nice guys. It was going to be a lot of cash.” And he got there and they had brought in a fighter from Russia. Gunn described him as huge, six feet five. He’s just wearing shorts, basically ready for him.

He said he remembered him as being very hairy. And there was a ring set up and the fight began. And the guy they had brought in, what’s interesting is even within kind of the bare knuckle world, there’s slightly different disciplines. And this guy fought a type of Russian MMA called Sambo. And apparently he said this guy had also been a trainer in the Russian army in the 1990s. And he tried to basically do some MMA moves on Gunn and then they said, “No, no, no. This was set as bare knuckle.” But the guy got frustrated and Bobby kept beating him and eventually just beat him unconscious. And a young guy who was in the crowd who must have been upset, he had bet money on that fighter, took out a gun and put it to Bobby’s head. And Bobby just stood there. And apparently they all looked to kind of the older Don and older gentleman who ran the organization and he told the younger guy to put his gun down and pay Bobby and let him go. He’d won a fair fight. And Bobby walked out with $50,000 in a brown paper bag that night. But it’s crazy. All the stories he has, going to Chinatown, going through storefronts, just like there’s underground basements where there’s all sorts of illegal poker games and gambling. He would describe going down one in Chinatown and there was dog fights going on at one room, the Chinese mob had brought in somebody from overseas and same kind of thing. They would just fight in these cramped spaces for cash.

But for Bobby, he was always at the end of the day taking the money and just leaving immediately. He said, “I’d take my kids to a park the next day. We’d go see a Pixar movie at the mall.” He said his grandfather said, “Always leave the bums at the gym.” So he was very tough and very adept and obviously able to survive and thrive in this very dangerous underground world. But at the end of the day, he just saw it as a job and wanted to get back to his family.

Brett McKay: Yeah. He was doing this for his family.

Stayton Bonner: Yeah.

Brett McKay: And he said sometimes he’d forget that he had a day job. Boxing was what he did at night. His day job was asphalt… Spreading asphalt. That was what he did. And so he was having to balance all that, but he managed to do it. So what’s the state of bare knuckle boxing today?

Stayton Bonner: Yeah, well I would not have necessarily expected this when I was running around with these guys 12, 15 years ago in these illegal matches, but it’s… Bare knuckle boxing has become the fastest rising combat sport in the world. And it’s funny, there’s a story in the book where Bobby Gunn goes to an Irish Mob fight. It wasn’t a faction he knew well, there were different factions. And actually they brought over someone from Ireland. He was there with David Feldman. David Feldman was from Philadelphia, a boxing and MMA promoter also overcame an extremely abusive, difficult childhood. His dad was a mob-backed boxing trainer, Marty Feldman, kind of a similar situation to Gunn. He just grew up fighting himself and he met Bobby Gunn and Gunn introduced him to the bare knuckle world. And David Feldman was a fighter, but he was also a promoter. So he had the business insight on this and said, “Wow, I think this could be a really great product. I think people would be interested in this sport, seeing it come back to life.” So David Feldman, who now has started the bare knuckle fighting championship, which had its first sanctioned fight in Wyoming, I was there for that. It was the first state to sanction it and make it legal. Bobby Gunn was on that card. And that first year they held a handful of events across the United States ’cause it’s… He had to convince each state to sanction this thing.

They made $500,000 gross. I was just with David Feldman a few weeks ago. They’re now valued at $312 million and they’re slated for 48 events this year in the United States and around the world. So it would not be coming back if it were not for Bobby Gunn. And then David Feldman has taken that idea and turned it into a truly legitimate sport with the bare knuckle fighting championship. And they’re just about to have their first event, their biggest card yet, in Los Angeles at KnuckleMania on April 27th.

Brett McKay: All right. So we might be seeing HBO matches here pretty soon.

Stayton Bonner: Yeah. It’s definitely on the upswing. And my book, Chronicles the history… The story of Gunn, but it also chronicles the early day of this… Days of this modern resurgence. And it’s just a wild story.

Brett McKay: Well, Stayton, this has been a great conversation. Where can people go to learn more about the book and your work?

Stayton Bonner: Absolutely. The book is Bare Knuckle: Bobby Gunn, 73-0 Undefeated. A Dad. A Dream. A Fight Like You’ve Never Seen available on Amazon, Barnes & Noble, a bunch of places online. And I’m on Twitter, Stayton Bonner.

Brett McKay: Fantastic. Well, Stayton Bonner, thanks for your time. It’s been a pleasure.

Stayton Bonner: Absolutely. Thanks so much for having me.

Brett McKay: My guest today was Stayton Bonner. He’s the author of the book Bare Knuckle. It’s available on and bookstores everywhere. Check out our show notes at where you can find links to resources where you can delve deeper into this topic.

Well, that wraps up another edition of the AoM Podcast. The Art of Manliness website has been around for over 16 years now, and the podcasts for over 10. And they both have always had one aim, to help men take action to improve every area of their lives, to become better friends, citizens, husbands, and fathers. Better men. If you’ve gotten something out of the AoM Podcast, please consider giving back by leaving a review or sharing an episode with a friend. As always, thank you for the continued support. Until next time, this is Brett McKay reminding you to not only listen to the AoM Podcast, but put what you’ve heard into action.

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