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Henry Tillman, the only man who defeated Mike Tyson twice as an amateur.

“Boxing is not a sport actually, for the actual boxer, it’s a lifestyle. You have to live it, live it, eat it, drink it, sleep it…”

If I told you, you would live a life of which on three days you would fight Mike Tyson, you probably wouldn’t want to wake up in the morning.

Henry Tillman woke up on all three of those mornings, and is even able to call himself the victor of 2 of 3 of those bouts. Henry Tillman is the holder of what is probably the least desirable of days to fight Mike Tyson, June 16, 1990; 125 days after Tyson suffered his first loss of his professional career. Tillman’s two victories over Mike Tyson came during the 1984 Olympic trials, when Tyson was 17 years old. Henry Tillman won Olympic Gold in 1984 by defeating heavyweight Canadian favorite, Willie De Wit, and went on to fight the aforementioned Mike Tyson, Evander Holyfield, and Bert Cooper in his professional career which spanned just slightly under eight full years.

Tillman has since earned a new respect in the boxing world. Henry Tillman has trained former IBF Heavyweight Champion Charles Martin since his first fight, and is still training him to this day. Charles Martin has a record of 25-1-1, with 23 knockouts. His opponents have a combined record of 547-184-25, and his only loss was to Anthony Joshua back in April of 2016. On October 25, 2017, I caught up with Henry Tillman and subsequently, heightened my boxing education. Here is our conversation:


How long have you been involved in boxing?

I started in 1982, March of 1982.

What drew you to boxing?

I was in the Youth Authority, California Youth Authority, the one I was at was called YTS. That’s where I started boxing.

Hobbies outside of boxing?

Yeah, golf, boat, Harley.



Hey Henry



Who was the most challenging opponent you faced?

As amateur, before the Olympics it was Tyson in the Olympic trials, and then Willie de Wit from Canada, during the Olympics. As pro, Holyfield, Tyson, Bert Cooper’s tough as hell too. Really, all fights was tough. You still go to training camp for eight, nine weeks. There’s nothing easy about boxing.

Who hit the hardest?

Why do people ask stuff like that? It’s not like you have a hit stat in your body that tells you “that was the hardest hit you ever had.” I mean, there’s guys that can’t even knock people out. They just get the right punch at the right time. Anybody over 200lbs’ll knock the hell outchu. There really is no right answer for that.

What was the best attribute of your skill set?

My hand speed, jab, I had a good right hand.

When you fought Tyson in 1990, how had he developed as a fighter since the first two times you fought him as an amateur?

I think we both developed, we both had to, we were pros. He just caught me with a good shot, top of the temple. That’s all that was, he was just ready, he was prepared. Coming off that loss to Buster Douglas, he had his hunger back again. Great fighter though.

Were you expecting Mike to be particularly more ferocious since he came off that Douglas loss?

Well, I think all fighters are a little more…especially a first fight back after a loss, you kinda have something to prove.

When you did fight Mike, what was your strategy, and how were you able to implement it?

Boxing, lateral movement, jab, stay off the ropes.

Who of your era would you have liked to fight that you didn’t get a chance to?

I never really got into it, I just fought as it went. I just left it to the matchmakers, the promoters, and the managers, I never got into all that trash talkin’ “I want to fight that chump,” that’s just not me. I aint never turn down no fight though.


Henry Tillman and Dangerman the Urban Superhero

What is the most fun experience you had while boxing?

The traveling, meeting a lot of good people. The traveling mostly, I really enjoyed all the traveling, and I met some really good people that I still know to this day, from boxing. And traveling to the Olympics from amateurs was really fun for me. But to me, amateurs was harder than pros for me. Because I fought a lot of tournaments, big tournaments, National, Golden Gloves, Pan-Am, World Championships, Olympics, stuff like that. And those are hard fights, you fight five times, and every time you win, the next guy is going to be tougher than the last guy. Because you’re knocking all of those guys off, and the next guy on the bracket, he’s knocking all of those guys off, every time you go up, the fight doesn’t get easier, it gets tougher. Your knuckles hurting, my arm, everything, and you still have got to fight. You fight every day.

Would you mind repeating all of those tournaments you were in?

National, National Golden Gloves, Pan-Am, World Championships, Olympics, and the international bouts, commonwealth. You see, back then, you’ve got to remember, Russians, Germans, and all of them didn’t go pro. So they were basically, pro amateurs, because their country was taking care of them. We were fighting guys that have been in the Olympics twice. That’s like me staying amateur after I win the Olympics, who the hell is going to do that? I was a pro pretty much, when I came out of the amateurs.


Rasheed Lateef, Dangerman the Urban Superhero with Obba Babatunde' in the ring. Henry Tillman is getting his fighter ready for the match.

So they stayed around in those amateur tournaments, but they were really pro level?

They were pro, but they were still doing the amateur stuff. Think about it, they’re paying their rent, their paying their whatever it is, their food, that’s a pro. See, there’s one punch for a trophy, and it’s another punch when a guy’s trying to pay his mortgage. Those are two different punches.

Do you currently train any pro or amateur fighters?

Charles Martin, heavyweight, Prince Charles Martin.

How long have you been training him?

I started him, zero fights to the heavyweight championship.

When you’re training a fighter, what do you appreciate most about him?

Their drive, they’re on time, coming to the gym, running, eating right, and just being a fighter, and living the lifestyle of a fighter. Boxing is not a sport actually, for the actual boxer, it’s a lifestyle. You have to live it, live it, eat it, drink it, sleep it. Everything you do has got to be towards your boxing. You’ve got to ask yourself “is this good or bad for my boxing?” 9.9 times out of 10, it’s bad for your boxing.

When you see people who are either working out, their amateurs, or they’re pros, what are the bad habits you see often of people?

The biggest mistake I see people do in boxing, is trying to emulate someone else. All these guys putting their hands way down, and get their head knocked off. Like Mayweather, he holds his left hand down here, but he’s been doing that since he was four. These guys today will do it in four months. Man, he’s been doing that since he was four years old. So it’s easy for him. His father and his uncle fought that way so, he grew up fighting like that. Rolling his shoulders. You saw what he did to McGregor, he put that glove right here, and his hands just did like this, let him punch himself out. After the fourth-fifth round, McGregor was so tired, he was punching like this. It was a good strategy, McGregor was bigger, stronger, he would just wear him down.



Henry Tillman hanging out with good friends after the Friday Night Fights


What message would you have for young fighters of today?

Well, you know, if you’re going to do it, you have to put your whole heart and soul and mind into it. There’s one thing about boxing, you can’t kind of box, I think I’m a boxer, I’m going to try to box, you’re either going to or you’re not. And like I say, you have to live the lifestyle, it’s way more than a sport, it’s a lifestyle. You can lose your life in it.

It’s more of a lifestyle, than a job or just a sport. Like being the police, that’s a lifestyle. He has to be that all the time. You never know when he might run into a cat he had to arrest from earlier on, and the guy might have animosity towards him, see him and try to do something to him. You’ve got to be a cop even when you’re at home, you’ve got to be a cop.

Same as a boxer?

Same as a boxer, got to be a fighter all the time, not sometime, not a weekend warrior, you know. It’s a lifestyle. A firefighter is a firefighter all the time. His training kicks in as soon as he sees the fire, his training kicks in. He forgets about his own life and everything, he goes and tries to save or whatever, and stop the fire. That’s kind of what you have to do as a fighter. You kind of, not forget about your ordinary life, but in a sense you do, you can’t really say “oh am I, is this going to be a day I’m going to get hurt, is this the day where I am going to get killed?” You know, “Is this the day I’m going to kill somebody?” You can’t think that way, you’ll never get it done. It’s like getting in your car, “is the day I’m going to run somebody over and kill them, or is this the day I’m going to have a car accident and die in the car?” You’ll never go any damn where.

Got to start the engine.

Right!!!!!!!


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