I was a street fighter with Kimbo Slice before making KO history in the UFC and promoting boxing leg

June 2024 · 3 minute read

Jorge Masvidal has had quite the journey from fighting on the streets of Miami to making history in the UFC and promoting his own shows with combat sports legends.

‘Gamebred’ first made a name for himself in 2003 at just 18, when he had a street fight against Kimbo Slice’s right-hand man, Ray, which subsequently went viral.

He was sitting in a McDonald’s drive-through when the call came from Slice, the late MMA fighter who organised and uploaded mutual combat street fights to YouTube, and he fought Ray later that day.

Despite being an undersized newcomer, Masvidal expertly handled his opponent and did so again when they rematched before he decided to pursue a legitimate fight career.

Masvidal told BBC Sport about his street fighting days: “There was never any animosity. It was just fierce competition and two guys going at it. If I’d lost, I would have gone over to him, shook his hand and hugged him.

“Me and Kimbo, rest in peace, we used to train at the same gym. He’d already seen me working out and we built up a little bit of a connection after talking a couple of times.

“That’s when he asked if I’d like to fight in his backyard. The rest is history.”

Over the next 15 years, Masvidal had 45 MMA fights and made a name for himself but suffered 13 defeats and never seemed destined for superstardom.

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However, after suffering back-to-back losses for the first time in his career the 38-year-old took two years away from the sport before returning with a new fighting mindset in 2019.

"I reverse engineered my whole career numerous times, but never in depth like I did this last time,” Masvidal explained at the time.  

“I'd seen every one of my decision losses in my head and went back. 'How could I have won that decision?' And then I immediately killed that person and thought and said, 'Why the hell would I look for a way to outpoint a guy?'

“I should be ending them. Like, make a math formula so that there's no judges involved. And that's all I've been trying to do and that's all I'm gonna do with what's left of my career."

Masvidal put Darren Till out cold in his comeback fight before doing the same thing to Ben Askren in just five seconds to secure the fastest knockout win in UFC history.

A massive ‘Baddest Motherf*****’ title fight with Nate Diaz followed and he ruthlessly dismantled the MMA legend over three rounds before the ringside referee waved off the fight.

At this point, Masvidal was the biggest star in the sport and remains one of the most popular fighters on the UFC roster despite losing his next three fights agaisnt Kamaru Usman, who beat him twice, and Colby Covington.

‘Street Jesus’ has parlayed his recent success into a new fight business and he promoted a boxing show featuring ring legend Roy Jones Jr., Jose Aldo, Anthony Pettis, Vitor Belfort, and other big-name MMA fighters earlier this month.

Masvidal has certainly come a long way from fighting on the streets for fun.

He’ll now try to secure his third welterweight title shot by beating Gilbert Burns at UFC 287 this weekend, although Dana White insists the fight is not a title eliminator.

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The UFC president has repeatedly claimed Leon Edwards will defend his belt against Covington next, but Masvidal believes another speculator knockout win will be enough to get a fight with ‘Rocky’.

It’s hard to back against him pulling it off after watching his journey from nothing to the very top of MMA's premier promotion.

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