The Fighting Life of Jorge Masvidal

The Fighting Life of Jorge Masvidal

By Ben Jessop

The extraordinary fighting life of one of the UFC’s most prolific welterweights.

November 12th 1984, Jorge Masvidal was born to a Peruvian mother and a Cuban father in the wild city of Miami, Florida. The story of how Masvidal’s father made it to the UK is nothing short of incredible.

Having escaped Cuba, after Communism took over in 1959, the now fourteen year old boy met with two grown men who he did not know and the three of them travelled by raft across the sea in search of a better life in the USA.

According to Jorge Jnr, whilst sailing across the ocean in blistering heat, the trio’s water supply soon ran dry and a few hours later a seabird landed on the raft and as the men looked at each other with dry lips and tired eyes, mayhem took over and Jorge Snr ripped off the head of the bird and drank it’s still warm blood.

Masvidal Jnr grew up in a fatherless home, after his dad had multiple run-ins with the law which spearheaded in an eighteen year prison sentence after being arrested for manslaughter prior to his son’s birth and then convicted of drug trafficking when Jorge was only four years old.

Despite his father’s bad life decisions, Jorge still took inspiration from him, knowing that when things got tough, he would be able to do whatever was required to overcome it.

As a child, Masvidal was moved through various neighbourhoods in Miami, including Cutler Ridge and Westchester but the family was always poor. Having shacked up with his aunt’s family, under his grandparents roof, Masvidal remembers his mother waking up at 4AM every day to work two jobs and still be the poorest family on the block. The vivid memories of his mother and family struggling became the motivation, as well as his biggest fear as an adult man.

Jorge was absolutely determined to never be in a position in which he was unable to provide a hot meal, or a roof over his children’s heads – of which he now has three.

It didn’t take long for Masvidal to become embroiled in the underbelly of Miami. As a young child, Jorge was known for continuously fighting to the point his mother forced him to enrol in a karate class under the watchful eye of Eric “El Tigre” Castanos – A Cuban kickboxing and Muay Thai world champion.

It didn’t take long before it became obvious Masvidal had a special gift for violence. It wasn’t his genius technical ability, but the heart he showed as soon as he stepped into the gym, he was born with the mentality of a fighter.

With the idyllic sway of mixed martial arts in the back of his mind, Masvidal struggled throughout school, constantly falling behind, despite earning a space on the high school wrestling team in 2000, he didn’t compete once due to his bad grades.

Though this didn’t spur him on to try and do better academically, all it did was push his interest in mixed martial arts to an obsession.

For the next few years, Masvidal poured all of his energy into fighting. Learning technique in the gym, and applying it in backyard bare knuckle fights in the Miami underworld. Masvidal soon acquired quite a name for himself, the skinny Cuban brawler. Willing to fight anyone, anywhere, in front of everyone. It wasn’t long before Masvidal caught the eye of the Godfather of backyard brawling – Kimbo Slice.

Kimbo continuously put Masvidal up for fights and each and every time he came out victorious but continued to maintain his down to earth, low-key personality. Little did Masvidal know, one of these backyard brawls would be the making of the man he is now.

Midway through a Big Mac and fries, Jorge’s phone began to ring and it was Kimbo. A fight, in one hour, in a backyard a few miles away. Of course, without hesitation Jorge accepted – and then in hindsight decided to ask who it was he was actually going to be fighting. It was Ray. Kimbo Slice’s most prevalent protégé and the fight was worth a couple hundred dollars.

Having continued to finish his big mac, fries and shake he began to walk to the location of the fight, knowing who Ray was didn’t seem to phase Masvidal at all. He rolled into the backyard and sized up his opponent, who had several years on Masvidal, as well as being six feet two inches and weighing over two hundred pounds of lean muscle, to the twenty-something onlookers this was bound to be a whitewash.

Looking at Masvidal, standing at five foot ten and 165 pounds, this was a David vs Goliath battle.

It took four and a half minutes, jabs and hooks and a relentless pace until the seemingly unbeatable Ray relented and he gave in, falling into a chair as a stream of blood flowed from his nose and mouth. The fight was filmed and put onto Kimbo’s YouTube channel, where he had an almost cult-like following. It wasn’t long after uploading the video it went viral, people stunned by this unfathomable win – who was this Cuban scrapper taking down beasts of the Miami underworld? Jorge Masvidal – people everywhere would soon know his name.

Off the back of his famous backyard brawl, it took a month for Jorge (with the help of Castanos) debuted in his first professional fight. At only nineteen years old, Masvidal faced off against another prospect, Brandon Bledsoe, in the Absolute Fighting Championship. A quick knockout win pronounced his arrival in professional prize fighting, loud and clear. The AFC was one of the first MMA promotions in Florida and often worked as a feeder league for larger promotions, like the UFC.

The purses ranged from $500 to a few thousand, but to people like Masvidal, the want to fight outweighed his need for cash.

Masvidal continued to fight for the next few years successfully, but often not earning enough to cover his living expenses. He needed a payday, and badly. Masvidal fought all of his way to the top of the AFC’s welterweight division, finally winning the title, you could see the larger MMA promotions circling the new champ – Masvidal basically had his pick of where to go, with the likes of Bellator, UFC, Strikeforce and the Japanese organisation Sengoku.

Jorge fought his way around North America and Asia, always brandishing the Cuban flag on his shorts, to him, it was a way to show homage to his heritage, and to the biggest missing piece in his life: his father.

Masvidal Senior wasn’t always present, or able to speak with his son but was dedicated to watching every one of his fights on the internet and seeing his son, fighting and winning, with the Cuban flag stitched into his shorts filled his father with pride.

When 2007 finally rolled around, Masvidal Senior was released from prison and the two of them made up on lost time and became extremely close, realising they had more than either of them realised in common.

Their first outing together took place right after his father’s release, they attended a strip club, along with Masvidal’s brother and soon a group of men, intoxicated and rowdy began to annoy the Masvidal family, showering them in dollar notes and getting too close for comfort – despite moving a few tables down to try and avoid conflict, the group followed Jorge and his family. Jorge politely told the biggest and loudest guy to back up and leave them alone, to which a balled up fist came flying towards Jorge, but off target. Needless to say, Jorge released a fury of viciousness, making quick work of the guy in front of him. Security soon intervened and Jorge found himself outside the club on his own, surrounded by the guy he’d just dropped along with all of his friends, but still Jorge refused to back down, fists raised he proceeded to take on the gang and about forty-five seconds later, Masvidal Senior and his other son joined in on  the ruckus.

Within two minutes, the group of men were sprawled out on the floor – in that moment Jorge realised where his gift had come from – his dad was a real fighter.


Continuing his professional prize fighting career, we can fast forward to 2013 – the year Masvidal finally made it to the UFC. He made quick works of UFC journeyman Tim Means and quickly was signed for a second bout, this time the fight was to be nationally televised, under bright lights and in front of a multitude of cameras, it was Masvidal’s first shot to really explode in a different way, that hadn’t been possible before.

Masvidal stood across from Michael Chiesa, the prospect who had recently won The Ultimate Fighter, who was now fighting in his hometown of Seattle. This was what Masvidal lived for – being the underdog, surrounded by people who doubt him and proving all of them wrong. Despite the fight going a couple of rounds, it wasn’t difficult to see that Masvidal was the superior fighter, when finally he was given the opportunity and managed to secure a D’Acre` choke and as the camera zoomed in to see Chiesa, breathless and gurgling, with his veins and eyes popping through the lack of oxygen, the arena fell silent and finally Chiesa decided to surrender with the tap. Masvidal had silenced the arena, this would quickly become the sound he cherished the most.

Since dismantling this prospect, Masvidal believes the UFC quickly learnt their lesson and decided not to match Masvidal with anyone they were trying to build into a star, he was too well rounded of a fighter, and too dangerous to pit against newcomers. Instead, they decided to hire Masvidal as some sort of title contender assassin.

People the UFC don’t think can be great champs, they pit against Masvidal in a bid to slow or stop their win streaks. The fight that threw Masvidal into the conversation of the top five came in January 2017 against Donald ‘Cowboy’ Cerrone, again, it took place in Cerrone’s hometown.


Masvidal, again looking for that eerie silence of a home crowd when their hometown hero loses. In the build up to the fight, Cerrone said during the press tour that he’d never heard of Jorge Masvidal, despite not much phasing him in terms of trash talk, this for some reason got under Masvidal’s skin and was not something he’d forget. In the second round of the fight, Masvidal unleashed a dangerous combination that rocked Cerrone enough for the fight to be waived off by referee Herb Dean and in the midst of that silence he’s been waiting, Masvidal approached Cerrone and said four words before walking away from the octagon: “You know me now”.

Having been catapulted into the top five of the welterweight division, Masvidal now found himself training at one of the best camps in the world: American Top Team and with a roster of ridiculously good fighters, including Amanda Nunes, Yoel Romero and Thiago Santos, it was safe to say Masvidal was in his element.

Despite working with arguably the best camp in the world, Jorge Masvidal was handed two losses in a row. One by Damian Maia via split decision and one via Stephen Thompson via unanimous decision, six months apart.

Losses were always a part of Jorge’s career, he’s never claimed to be the perfect fighter but he is someone who thrives off of the violence that MMA brings, the pressure and danger is something he cannot live without. So when the UFC offered him the opportunity to fight one of their biggest stars and a real contender for the welterweight championship against Darren Till, in London – Jorge was inevitably going to say yes, and sign the dotted line.

Leading up to the fight, Jorge was put down as the big underdog, and Till was the golden boy who could do no wrong. People saw this as a formality in Till’s endeavour to get back to a chance at the title – People couldn’t of been more wrong.

Despite a few mishaps in the first round, namely a crotch shot and an eye poke, the second round was Jorge’s round, all the way through until three minutes in. Jorge caught Till with an absolute bomb of a left hand, leaving him out cold on the canvas.


Yet again, finally, Masvidal got to hear that utter disbelief as an entire arena falls silent in shock. He’d proved everyone wrong – again.

Jorge Masvidal faces a fresh challenge on 6th July 2019 where he’ll face renowned all american wrestler Ben Askren who will be fighting for the second time in the UFC but highly regarded as one of the most dangerous men in the division and after a controversial win over Robbie Lawler as his UFC debut, Askren will be desperate for a dominant win to prove his position in the organisation.

But people should be cautious not to write Jorge Masvidal off – he’s a brilliantly all rounded fighter with outstanding wrestling and every single time someone puts him down as an underdog, or claims he stands no change, Masvidal gets that little bit stronger.

Jorge Masvidal has always been, and remains to this day one of the realest fighters in professional MMA anywhere in the world – something that Leon Edwards learnt all too well when he got served with a ‘three piece and a soda’ backstage at the Till fight.

Currently sitting with a 33-13-0 record, he’s one of the most decorated fighters in the world and for good reason – he is a man that was born to fight, and he has lived that purpose to its full potential.

If you’re looking for a man who epitomises that of a world class fighting man – Look no further than Jorge Masvidal.

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