The story behind the fastest knockout in UFC history

It was July 6, 2019, and UFC 239 had a stacked main card. Light heavyweight champion Jon Jones was defending his belt against heavy hitter Thiago Santos, and Holly Holm of "head-kicking Ronda Rousey fame" was challenging the female GOAT, Amanda Nunes, for the bantamweight strap. But despite these stars atop the card, when the dust settled in the Las Vegas T-Mobile Arena, the only fight anyone could talk about was Jorge Masvidal versus Ben Askren.

The third fight on the main card, Masvidal versus Askren was a genuine grudge match, with weeks of buildup between a no-nonsense street fighter and a trash-talking wrestler. Fans were expecting an insane back-and-forth between two of the UFC's most exciting welterweights, but when these warriors faced off, the fight was over in less time than it takes to tie your shoes. At UFC 239, MMA fans witnessed the fastest knockout in UFC history — one that started with a lot of drama and ended with a lot of damage.

The record for fastest UFC knockout was set by Duane Ludwig (sort of)

Jorge Masvidal and Ben Askren made history at UFC 239 with a lightning-fast knockout that turned the MMA world upside-down. But who held the UFC knockout record before that fierce and fateful night? Well, that would be Duane "Bang" Ludwig, an accomplished fighter with an MMA record of 21-14. At UFC Fight Night 3 in January 2006, Ludwig made history with a vicious shot to Jonathan Goulet's jaw, sending his opponent to the canvas at the 6-second mark.

However, the UFC is one big soap opera, and the story behind Ludwig's knockout is full of drama. Even though the ref called off the fight at around 6 seconds, the official timekeeper screwed up somehow and didn't stop the clock until the 11-second mark, which is the fight's official stop time. But despite technicalities, White and the UFC decided to ignore those extra seconds and declare Ludwig the owner of the company's fastest KO … until Masvidal and Askren crashed the party.

Ben Askren - The greatest fighter never in the UFC

So let's introduce the first man involved in our brutal little dance: Ben Askren, a curly-headed wrestler from Wisconsin. For years, many considered Askren the greatest fighter who'd never fought in the UFC, and his record outside the Octagon was phenomenal. He was a two-time state championship wrestler in high school, and after earning a full scholarship to the University of Missouri, he won the NCAA I Championships in 2006 and 2007. On top of that, his weird, unconventional wrestling style earned the four-time All-American the nickname "Funky."

From there, Askren competed in the 2008 Beijing Olympics (alongside future UFC champions Henry Cejudo and Daniel Cormier), but after failing to medal, he took his wrestling game into the world of MMA. He quickly made his way to Bellator — today considered the second biggest MMA promotion — where he captured the welterweight title and defended the belt five times before Bellator let him go. Afterward, Askren quickly joined the Singaporean promotion ONE Championship, and in true Funky fashion, he quickly nabbed the welterweight belt. The Wisconsin wrestler eventually "retired" in 2017 with a mind-blowing record of 18 wins, one no-contest, and zero losses … but MMA retirements never last long.

Why did it take so long for Askren to join the UFC?

Up until 2018, Ben Askren had never been in the UFC, but it wasn't for a lack of trying. In between his reigns at Bellator and ONE, the wrestler actually tried signing up with the world's biggest MMA promotion, but if you want to join the Ultimate Fighting Championship, you've got to impress Dana White. The outspoken president of the company, White was not impressed with Askren's record. Believing Bellator was full of chumps, White told Askren to sign with another promotion called World Series of Fighting and prove himself there. This did not sit well with Askren, who ignored White and joined ONE instead.

Ever since White dismissed Askren's abilities, the two haven't exactly been besties. In fact, the two have a history of trading insults back and forth. For example, Askren called White "a freaking scumbag" and claimed he didn't need the UFC to be great. As for the UFC boss, White called Askren a "moron" and made fun of his grinding style by saying, "When Ambien can't sleep, it takes Ben Askren." With that kind of bad blood, it seemed unlikely that Askren would ever be welcome in the Octagon, but that all changed when the UFC decided to make history.

The first trade in UFC history

In 2018, fight fans dropped their collective jaw when the Ultimate Fighting Championship completed the first "trade" in UFC history. The company was releasing one of its best fighters, Demetrious Johnson, so he could go over to ONE Championship. In return, ONE would release the recently "retired" Askren from his incomplete contract so he could compete in the UFC. As the UFC has always refused to co-promote with other MMA organizations, the news was truly shocking.

Stranger still, Johnson was considered by many to be the greatest fighter of all-time. Up until recently, he'd been the flyweight (125 pounds) champion and had set a title defense record with 11 victories. However, his relationship with the UFC was always a tad contentious. Plus, his coach Matt Hume was the vice president of ONE, so it makes sense that Johnson's team would propose the trade, and that White — never a fan of the flyweight division — would agree. And as a result, curious fans would finally find out if Askren could dominate in the UFC.

Askren's first UFC fight was incredibly controversial

When Ben Askren arrived in the UFC, he immediately put the welterweight division on notice. After all, the man is a notorious trash talker, and he let everybody know he was here to drop bombs and crack skulls. And when he done roasting everyone inside and outside the division, the UFC paired him up with ex-champion "Ruthless" Robbie Lawler, a man with hands made of steel.

Askren stepped into the Octagon for the first time in March 2019, and while he walked away the victor, his match was marred by controversy. Just 14 seconds in, Lawler picked Askren up over his head and slammed him down on the mat. He then turned Askren's face into bloodsoaked punching bag, but the wrestler survived and caught Lawler in a bulldog choke. The choke was deep, Lawler's arm went limp, and referee Herb Dean called off the fight.

But the moment Askren let go, Lawler immediately stood up — not something you do when you're unconscious — and protested, claiming he was never out. Dean's decision tore in the MMA world in two, with some fans siding with Askren, and others claiming Lawler was just relaxing himself for a moment and letting the wrestler waste his strength. Dana White said it was a bad call and that there should be a rematch, but as for Askren himself, he had no interest in running the fight back, saying, "I feel great. I went and did my job." Despite the controversy, Askren proved he could take punishment and hang with the UFC elite. Now, all he needed was a new opponent.

Jorge Masvidal's UFC journey started with backyard brawls

It takes two to tango, and standing across from Ben Askren, we've got Jorge "Gamebred" Masvidal. The man got his nickname because he was "bred to fight," and the always-game Masvidal has been drawing blood his entire life. The son of a Cuban immigrant, Masvidal grew up poor, hungry, and mostly in a single-parent household as his dad spent a lot of time in jail. But while Masvidal often missed meals, he loved to fight.

According to the Miami New Times, Masvidal got involved with karate and wrestling as a youth, but he didn't compete in prestigious tournaments. Instead, Masvidal made a name for himself by sleeping fools on the streets. He'd been fighting for cash since he was 16, but his big moment came when the 19-year-old got a call that Kimbo Slice — the backyard brawler of viral video fame — needed somebody to face his protege, Ray. The bareknuckle match was going down in an hour, so after scarfing down some McDonald's, the Miami-native made his way to the yard, ready for war.

At first glance, it looked like Masvidal was in for a beating, since 6'2" Ray was 4 inches taller and over 35 pounds heavier than his opponent. But size don't mean a thing when you've got those flying fists, and Masvidal wrecked his foe in under five minutes. The fast and furious fight got lots of attention, turning Masvidal into an online sensation and setting him down the path of UFC stardom.

Masvidal makes his way to the UFC

Just a month after showing up in a Kimbo Slice video, Jorge Masvidal got his first professional fight with tiny organization called Absolute Fighting Championship. And in true Gamebred fashion, he KO'd his opponent in the very first round. The Miami native would go on to fight in tiny promotions like Bodog Fight and Shark Fights, as well as bigger companies like Bellator and Strikeforce, before making his UFC debut in 2013.

As a member of American Top Team, Masvidal won his first UFC fight by unanimous decision, and from there, he proved himself to be an always-dangerous fighter. But things really started looking up for Gamebred in 2016 when he went on a three-fight win streak against impressive names like Ross Pearson, Jake Ellenberger, and Donald "Cowboy" Cerrone. If Masvidal could just win his next fight, he was looking at a title shot against then-welterweight champion Tyron Woodley.

But first, the 170-pound fighter would have to get past Brazilian jiu-jitsu expert Demian Maia. The BJJ specialist was riding a six-fight win streak, and while Masvidal took the match to a split decision, Maia overpowered him on the ground and walked away with the win. Losing his shot at welterweight glory was especially painful for Masvidal, and with his win streak broken, he hoped to bounce back at UFC 217, one of the biggest events in UFC history. Unfortunately, he was out-pointed by karate stylist Stephen Thompson. With back-to-back losses, Masvidal disappeared from the UFC for over a year, but when he returned, things got graphic.

Masvidal's amazing night in London

During his MMA sabbatical, Jorge Masvidal showed up on a Spanish-language reality show called Exatlon Estados Unidos. An athletic competition for the fittest people on the planet, the experience helped Masvidal find new focus. As he explained to ESPN, "Being on that show, you don't have a phone or TV, it's just you with your own thoughts, working out and being in nature. … Fighting was always on my mind."

Reinvigorated and ready to rock, Masvidal returned to the UFC in March 2019 to fight Darren Till in London. The UFC was hoping Till would become a star, and when the British bruiser walked out to his signature theme song, "Sweet Caroline," the crowd erupted with excitement. Everybody was rooting for their fellow countryman — who absolutely dwarfed Gamebred — but Masvidal silenced the crowd with a left hand from hell, dropping Till cold in the second round. It was a major moment for Masvidal, but his amazing night in London wasn't over yet.

Three piece with a soda

Jorge Masvidal shocked MMA fans around the world when he knocked out the monstrous Darren Till in the first round of their fight. But that was just the beginning. After introducing Till to the canvas, Masvidal was backstage, giving a post-fight interview, when somebody started hurling insults at him. That somebody was UFC fighter Leon Edwards, an up-and-coming welterweight who was no fan of Masvidal's. When Gamebred heard the trash talk, he calmly put his hands behind his back, strolled over to Edwards, and ruined the man's night with a flurry of punches. The incident was captured on film, and suddenly, Masvidal was all over the news. When asked about the backstage brawl by ESPN, Masvidal claimed that Edwards was about to attack. "You're not going to get a hit off on me," Masvidal said. "So I had to give him the three piece with the soda and then just glide out of there, you know?" The footage, coupled with the new catchphrase, grabbed everyone's attention, and suddenly, it became crystal clear that this hot-headed Cuban was the perfect man to tangle with Funky Ben Askren.

Masvidal vs. Askren starts with a war of words

Jorge Masvidal was going to fight Ben Askren in the Octagon, but first, he would have to win a war of the words against the welterweight wrestler. After all, Askren was famous for his poisonous tongue, and he was ready to rip Masvidal apart with insults.

See, way back in the day, before Askren joined the Milwaukee team Roufusport (home to ex-champs Anthony Pettis and Tyron Woodley), the wrestler spent some time at Masvidal's camp, American Top Team, where the two trained together. This provided Askren with the perfect material to roast his opponent, and he began bragging how he'd out-wrestled Masvidal. On top of that, he disparaged Gamebred's abilities, calling him a "pretty simple" fighter who would be "pretty easy" to beat.

Askren kept poking Masvidal, taunting him on Twitter for never having a belt and making fun of his fashion choices. However, Masvidal didn't have a great sense of humor about all the put-downs coming his way. The Miami fighter grew furious, called Askren a "fake" and a "coward," and said he was going to "make sure his bloodline doesn't reproduce."

On the Joe Rogan Experience, Masvidal got especially sadistic, saying, "I don't want to knock [Askren] out early on. … If I get the chance to torture that guy for 14 minutes and 50 seconds before I stop him, that's what I'm gonna do, man." But when Askren and Masvidal stepped into the Octagon on July 6, that's definitely not what happened.

The fastest knockout in UFC history

The date was July 6, 2019. The setting was the T-Mobile Arena on the Las Vegas Strip. It was UFC 239, and two championship fights headlined the event. But despite the gold at the top of the card, the people's main event was Jorge Masvidal versus Ben Askren. The trash talk had been intense. Askren's controversial last fight loomed large. And everybody wanted to know if Gamebred would serve up another three piece with soda. Would Askren take Masvidal to the ground and smother him on the mat? Or would Gamebred stuff Funky's shot and work him over with some hellacious combinations?

Well, pretty much the moment that referee Jason Herzog started the fight, it was all over. Askren began moving toward the center of the cage and suddenly Masvidal took off sprinting straight at his opponent. Ever the wrestler, Askren's instincts kicked in, and he ducked down, preparing to shoot — exactly what Masvidal wanted. As Askren's head went down, Masvidal came soaring off the mat, smashing Askren in the face with a flying knee. The wrestler crumpled to the ground, his arms stiff at his sides, and Masvidal delivered a couple nasty punches to Askren's face before the ref could step in.

The fight was over in just five seconds. Askren had just been handed his first loss, the crowd was going wild, and the man they called Gamebred had made UFC history.

The aftermath of Jorge Masvidal versus Ben Askren

The moment referee Jason Herzog ended the fight, Jorge Masvidal began to celebrate. While he was still down on all fours, he pounded the mat and shouted at the unconscious Askren. And when Gamebred got back to his feet, he stiffened up and tumbled to the canvas, doing a perfect impression of Askren going cold. The man was still revved up during the post-fight interviews, saying, "I gave [Askren] what he deserved." And when asked if those extra punches after Askren was unconscious were necessary, Masvidal responded, quick and cold, "They were super necessary."

As for Askren himself, the man was flat on the mat for quite some time, but after waking up and shuffling out of the cage, he took to Twitter to say, "Well that sucked." A few days after, Askren admitted that he couldn't remember the flying knee, but he also defended those extra shots thrown by Masvidal, saying, "I knew what I signed up for." But while it might've been a humbling experience for Askren, it was a career-defining turn for Jorge Masvidal. He'd had 46 professional fights heading into UFC 239, and after 16 years in the sport and a five-second knockout, Gamebred was finally a star.

The flying knee was no fluke

Did Jorge Masvidal decide to throw a flying knee right there in the cage? Did he just get lucky and land the perfect shot? As it turns out, Masvidal had actually been working on that move for months. Yeah, at first he wanted to torture Askren across three rounds, but as Masvidal explained to ESPN, "Then I decided, 'You know what? I'm going to check him right out the gate and see where he's at."

Masvidal spent his entire fight camp drilling that knee. "He was, all the way down to the last day, drilling that technique," said Masvidal's coach, Mike Brown. "Literally the day of [the fight], we were in the cage messing around with it so he could get his footwork and his timing right." Obviously, if the flying knee didn't land, Askren would grab Masvidal and dump him on his back, but Gamebred believed so strongly in his own wrestling abilities that he wasn't afraid of what would happen if the flying knee misfired. But, of course, the move went off perfectly, and as Askren hit the mat, Masvidal made his way into the history books.