Philly underdog Gabriel Rosado was a street-fighting 6-year-old, but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time

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Philly underdog Gabriel Rosado was a street-fighting 6-year-old, but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time
Gabriel Rosado.Photo by Patrick Smith/Getty Images
  • Gabriel Rosado fights Daniel Jacobs in Hollywood, Florida, on Friday.
  • He is a huge underdog and victory would likely be one of the biggest boxing upsets of 2020.
  • Rosado's life story is one of two fighting communities colliding. He grew up in the fight-crazy city of Philadelphia, and has Puerto Rican heritage.
  • Rather than get side-tracked with the money fights in the division, he is focused only on Jacobs as a win would write his own Rocky story.
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Philadelphian underdog Gabriel Rosado was a street-fighting 6-year-old but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time.

A 34-year-old veteran of 39 pro fights, Rosado returns to the ring Friday for the first time in the pandemic, and takes on Daniel Jacobs at the Seminole Hard Rock Hotel and Casino in Hollywood, Florida, in a super middleweight match which tops the five-bout Matchroom USA-promoted card on DAZN.

Rosado is not expected to beat Jacobs, who is a former champion looking to use the Philly fighter as a stepping stone toward another title fight so he can reclaim that lost championship status.

Regardless, Rosado told Insider this week that he sees specific weaknesses in his opponent, and will look to expose those so he can snatch the momentum Jacobs has, and make that title shot his own.

The fight is one Rosado had been hoping would materialize since before the coronavirus jeopardized live events early this year. He's now excited it's finally here, ready to compete once again, and try to prove critics who give him little to no chance of winning wrong.

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"He has speed and he can punch, but I wouldn't say he has the best defense — that's one of his weaknesses," Rosado said of Jacobs.

"He does get touched, gets hit. I just feel like that at this point in our career, we both have 13-14 years as professionals. It'll come down to skill, but mainly the will … who really wants it?"

Jacobs turned pro in 2007, has strong wins over Caleb Truax, Peter Quillin, and Sergiy Derevyanchenko. He also has three defeats on his ledger, losing to Dmitry Pirog, Gennadiy Golovkin, and Saul Alvarez — Insider's No.1 boxer in the world.

On what he could learn from his opponent's losses and look to replicate on fight night, Rosado said: "Every fight is different. In the Canelo and Golovkin fights, they applied really smart pressure on him and made him a little bit uncomfortable.

"But my style is different. And I think it's just about being smart, keeping the head offline. A lot of head movement.

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"Canelo made him miss a lot. Danny's a quick guy when it comes to throwing one shot, but with combinations he's not a fast guy."

Rosado has been fighting since he was six-years-old

Philly underdog Gabriel Rosado was a street-fighting 6-year-old, but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time
Daniel Jacobs and Gabriel Rosado faced-off Thursday.Photo by Ed Mulholland/Matchroom Boxing

Rosado was born in the city that spawned boxing legends 'Smokin' Joe Frazier, Bernard 'The Executioner' Hopkins, Jersey Joe Walcott, and the "Rocky" movie franchise.

He carries that distinctive boxing culture with him today, despite relocating to Los Angeles six years ago. There he opened his own gym called Badlands, a name riffing on the "Badlands" area of North Philadelphia, which is renowned for its open-air drug markets and drug-related violence.

Puerto Rico —another region that has acted as a conveyor belt for top tier boxers like Wilfredo Benitez, Miguel Cotto, and Felix Trinidad — is also in Rosado's blood.

"It's the best of both worlds," Rosado said of a teak-tough fusion of two rich fighting communities.

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"Philadelphia is a fighting city," he told us. "We call it boxing headquarters."

A post shared by KGR (@kinggabrosado)

And fighting is something Rosado has been doing for decades, even going back to when he was a kid.

In the late 1980s, Rosado's brawls weren't started over a girl they liked in class or a stolen basketball, but because it was fun and there was pride on the line.

"I've always been a fighter growing up," said Rosado. "Philly is a tough neighborhood. I started fighting in the first grade all the way to high school — it was just normal to have a fight every day.

"Sometimes the fights weren't even about not liking each other and were just about being competitive. There's another kid to fight, I think I'm better than him and he thinks he's better than me, so after school we meet up around the corner and handle it. You'd pull up and shake hands after. It was all pretty normal."

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Rosado's life choices as a youngster would likely have saddened his parents who were pastors at a Philly church before they separated when he was 13, as reported by The Philadelphia Enquirer, because through those years they were also getting phone calls from disappointed teachers.

It appeared to be at odds with a key part of his life — his faith.

Though Rosado dropped out of school aged 18, he found his calling in Philadelphia's boxing clubs where he seemed to thrive representing his gym, going to another boxing club to knock out their best guys in hard sparring sessions.

"You have to have that reputation for being tough in the gym," he said, regarding what epitomizes Philadelphia's boxing culture.

"There's no such thing as sparring days. It's more like a war, knocking people out in sparring. You go to someone's gym and you better represent. And the man in that gym better make sure they represent for their gym — it's a pride thing.

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"You don't really have too much but respect in the city, and getting off on a top guy from another gym is a big deal.

"That's why with Philly fighters you see they're tough, don't quit, and they're mean. It's just the way we grew up in the gyms."

Felix Trinidad sparked Rosado's love of boxing, and Mike Tyson cemented it

Philly underdog Gabriel Rosado was a street-fighting 6-year-old, but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time
Photos by Getty Images

Shortly after Rosado began street-fighting as a young kid, Felix 'Tito' Trinidad won his first world championship — the IBF welterweight world title. The Puerto Rican beat Maurico Blocker in the second round of a June 1993 bout.

Over the years he added further notable victories to his resume, defeating countryman Hector Camacho, the all-time defensive wizard Pernell Whitaker, and even Oscar de la Hoya.

It is no surprise he was a hero to the young Rosado. Trinidad was a pin-up for many Puerto Ricans as a young, fit, and massively-successful man.

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"I was a big Tito Trinidad fan," Rosado said. "I wanted to be like Tito. So, with the street-fighting I was thinking, 'Man, I can fight … I can be like Tito.' So I joined a gym and turned street-fighting into something positive."

Insider asked him if he's ever told Trinidad to his face that he was the main reason he got into boxing, perhaps avoiding walking down an alternative path that could have gotten him into trouble.

"I haven't, but, man … that would be on my bucket list."

Trinidad's era as a mind-blowing operator from the 147-pound weight class through to 160 followed Mike Tyson's time, who wrecking-balled his way through the heavyweight scene in the late 1980s and early 1990s.

Tyson, too, shaped Rosado's life.

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"He's just a savage but a student of the game," Rosado said. "He knows his boxing like a crazy encyclopedia, and I can relate to a lot of things about Mike Tyson.

"Tyson is an example of how strong the mind is. When Mike had [his former trainer] Cus D'Amato … he was unstoppable.

"But when he lost that, he lost that focus, confidence, and things went downhill for him.

"Mike is a good example of keeping your mental [game] locked in. Because you're unstoppable when you have that and you are on point.

"I learned a lot from Mike and would put him right there with Tito as far as inspiration."

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Tyson returns to the ring Saturday with Roy Jones Jr. for an exhibition as highly-anticipated as it is weird, as the organizers have been at odds with the commission over what the ruleset of the show actually is.

The California State Athletic Commission has forbidden both athletes from pursuing a knockout, which the organizers — Triller and League of Legends — is attempting to override by saying the fight can finish early.

Rosado laughed at the thought of Tyson and Jones holding back. "Those guys are fighters. Once a fighter, always a fighter.

"When the moment comes when someone actually gets touched and they start to feel embarrassed, they're going to come out swinging. Mike doesn't even know how to fight soft, he'll rip your head off.

"He has that switch and when that switch is gone, it's on. There's no telling what's going to happen. Who knows what we're going to see, but I doubt it's going to be soft."

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Rosado knows he's the underdog in his fight, but is motivated by what victory would mean

Philly underdog Gabriel Rosado was a street-fighting 6-year-old, but got inspired to box when he saw Mike Tyson and Felix Trinidad for the first time
Photo by Ed Mulholland/Matchroom Boxing

Rosado is a +1500 (15/1) underdog heading into Friday night's fight with Jacobs. He is not tipped to have much chance of victory, but knows a win — however unlikely — catapults him into title contention. It would be his own Rocky story.

"The 168-pound division is loaded with big names, superstars, and a few world champions. I'm excited about it," he said.

"I'm looking forward to the fight, and I'm not looking past it by getting sidetracked with Canelo, David Benavidez, Caleb Plant, or any of the other champions in the division.

"Jacobs is a former champion so a win over him is as good as anything else. The fans will be ready to see me in a big fight after as [it would be a win] that puts me right back into title contention.

"I've been focusing on him for the entire year, and only concentrating on that.

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"A victory would be huge."

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