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There’s a picture hanging in the Renzo Gracie Academy in New York City that isn’t the typical one. It’s not a photo celebrating any of Gracie’s big wins over the likes of Oleg Taktarov, Maurice Smith or Pat Miletich. Instead, students of the renowned jiu-jitsu black belt see Gracie at a low point, a 2000 loss to Kazushi Sakuraba that ended via technical submission when the famed “Gracie Hunter” broke his foe’s arm.

Why?

“When you win, it’s easy to forget all the hardship that you went through to get the win,” Gracie told me in 2010. “You get so excited with the victory and the people around you congratulating you and hugging you, you completely forget all the mistakes you made in that fight. But when you lose, you know them, and you will never forget them. So I made sure I put that picture here, and actually that’s the only picture I have here, hanging on the wall. It’s to remind me constantly that a fight is only finished when the bell rings and the ref pulls you guys apart. Every time I walk in, I see that picture, and remember that I’m not perfect. I need to improve, I need to get better, and I need to make the people under me better, so they don’t go through that.”

THE WILD RIDE OF HARLEY FLANAGAN: Part One | Part Two | Part Three

That lesson isn’t lost on Gracie’s students, such as black belt Harley Flanagan.

“That picture says so much about Renzo’s character and what an honorable man he is,” said Flanagan. “Most people have a hard time, first of all, accepting defeat in life in any shape or form. But to be able to have your arm broken by somebody and stand up and shake their hand and smile at them and say, ‘Good job,’ it shows what kind of character he has that he can have that kind of graciousness in defeat, and we should all aspire to be more like that. There’s a saying in jiu-jitsu: you don’t lose in jiu-jitsu, you learn, and if could all take that with us in life, we would really improve our lives. He broke his arm, he was in a lot of pain. He wasn’t gonna let it show; he smiled at him and he shook his hand. To me, that says right there, that’s a bad motherf**ker. And God bless him, we should all aspire to be bad motherf**kers like that, to be able to suck up our losses in life and be graceful and honorable in victory and in loss. Life is nothing but  a learning experience and a lot of experiences, good and bad. If you know how to look at it, you can really appreciate it for what it is in there. I learned a lot about life from being with Master Renzo, and not just about jiu-jitsu. I learned a lot about myself and a lot about life.”

Flanagan lived a lot of life before he stepped into the Renzo Gracie Academy in early 1996. There were some good times, some bad, but all memorable. And while his life is as settled as it’s ever been at 54, with a Cro Mags tour in 2022, a documentary by Citizen Ashe’s Rex Miller, and a happy family life with his wife and two sons, the fighter in the New Yorker has always been there. And if not for the fact that the UFC arrived in 1993, when he was 26 years old and already established in the music world, he might have taken a different path in life.

“If MMA would have been something that was happening in the 80s, there’s definitely a chance that I would have wound up going that route,” he said. “I fought a lot as a kid, and in my neighborhood, it was kind of unavoidable. And if there would have been a platform to actually make a living and release some of that pent-up aggression, it would have been helpful. I probably would have done a lot less things on the street that I regret now in my adult life.”

What’s done is done, though, and once he began training with Gracie and company, he knew that eventually, he wanted to test himself in an MMA fight. The only problem was that in 2007, MMA wasn’t legal in New York. Enter the Underground Combat League.

“I just wanted to fight,” Flanagan said. “We would have these events at MMA gyms and boxing gyms and places like that after hours. You’d buy tickets in advance and you’d find out the location the night before. You wouldn’t even know who you were fighting. You wouldn’t know who you were fighting, there were no weight classes, and gloves were optional.”

Having grown up taking part in streetfights, was Flanagan immune to pre-fight jitters?

“There were nerves, but I had been in real fights and I felt like what’s the worst thing that’s gonna happen? I’ll get knocked out? For me, it was really about, can I get a takedown on someone who’s actually trying to f**k me up?”

The first fight went according to plan. The second, not so much.

“I did one that I won real quick because I got a takedown and I cranked his ankle,” Flanagan recalls. “This was before anybody was doing stuff like that and I always liked knees and ankles because they’re easy – they’re right there. Back in the day I used to let people put me in half-guard just so I could turn around and take their knee from them. The next fight, I fought this kid who was 25 and I was 40 or 41. And this kid was undefeated. I think I made it to almost the end of the second round. I got a takedown, we were exchanging, and he caught me. My face was against the canvas, and it was like bam, buh ba blam bam. (Laughs) I tried to bump his ass off and get caught in an armbar. I felt like I could power out of it and I was about to try to yank out of it and the ref stopped us. And thank God, because I probably need my arm. I am after all a bass player.”

Flanagan laughs, and it’s the reaction you get from a real fighter. For guys like him, the fight isn’t about bad blood or grudges or sitting and dwelling on a defeat for months. It’s a competition, a way to test yourself, and when it’s over, it’s over.  

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“Me and the kid went out and got drunk and had a laugh,” said Flanagan about the aftermath of his second fight. “It was just a good time. I remember the next day I dropped my kids off to school. I had two big-ass black eyes and everybody’s looking at me. I came back that night, my kids’ mother was like, ‘What the f**k happened to you? I didn’t think you were gonna have a f**king fight.’”

Nobody said life with Harley Flanagan was going to be easy. But it was always going to be interesting. And with two fights under his belt, the 41-year-old assumed his run in the fight game was just getting started.

“I thought, ‘This was fun. I could do this s**t. Then I went to the next one and I remember seeing a couple dudes get f**ked up so bad that I was like, maybe this is not a great idea. It looked like one of those old school Tank Abbott knockouts. The dude just looked like a broken piece of furniture.”

Just like that, Flanagan called it a day and never looked back. He still had jiu-jitsu, family, music and a life that one day would result in a book (Hard-Core, Life On My Own) and soon a documentary. He made it. And he doesn’t take any of this for granted.

THE WILD RIDE OF HARLEY FLANAGAN: Part One | Part Two | Part Three

“I count my blessings every day,” he said. “I take the good and the bad and all of it. Even with the hell that I’ve been through in a lot of ways, I really love life. I love it.”

And as filming of the documentary is proving, plenty of people are loving him back.

“There’s people from all different eras of time that I have known throughout the course of my life,” Flanagan said. “And it’s pretty intense, man. It’s humbling. I shouldn’t have been so self-destructive and hard on myself for years because there were a lot of people who were rooting for me and I didn’t realize it.”

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