Masvidal Vs. Askren: Iconic KO & What Happened Next

Introduction: The Fight That Changed Everything

Alright, guys, let's talk about one of the most jaw-dropping moments in UFC history, a fight that sent shockwaves through the entire mixed martial arts world and permanently etched itself into the annals of combat sports: the epic showdown between Jorge Masvidal and Ben Askren at UFC 239 in July 2019. This wasn't just any fight; it was a clash of titans with wildly different styles and even more contrasting personalities, culminating in an instant classic that nobody, not even the most seasoned analyst, could have predicted. Before this incredible encounter, Jorge Masvidal was a respected but perhaps under-the-radar veteran, a gritty street fighter from Miami with a deep resume but few mainstream headlines. He was known for his slick striking and uncompromising toughness, a true "Gamebred" fighter who always brought the fight to his opponents, yet often found himself on the wrong side of close decisions or simply not breaking through to superstardom. On the other side of the octagon was Ben Askren, an undefeated Olympian, a collegiate wrestling phenom, and a former champion in both Bellator and ONE Championship. Askren, nicknamed "Funky," was making waves in the UFC after a high-profile trade, bringing with him an unblemished record, an unparalleled grappling game, and a loud, in-your-face trash-talking style that had quickly made him a polarizing figure. This fight was designed to be a definitive test for both men: Masvidal looking to finally crack the elite tier, and Askren aiming to prove his wrestling dominance could negate anyone's striking, even against a dangerous opponent like Masvidal. What unfolded in those unforgettable five seconds wasn't just a win or a loss; it was a moment of pure, unadulterated chaos that redefined careers, created legends, and provided us with one of the most iconic knockouts in UFC history. The aftermath of this particular fight resonated deeply, altering the trajectory of both fighters' careers in ways they, and we, could barely imagine at the time. This article will delve deep into that pivotal moment and explore the fascinating journey each man took after the initial shock wore off.

The Epic Build-Up: A Clash of Worlds and Words

The anticipation leading up to the Jorge Masvidal vs. Ben Askren fight was absolutely palpable, fueled by a compelling narrative of contrasting styles and a healthy dose of pre-fight animosity. On one side, we had Jorge Masvidal, a fighter who had truly paid his dues. He was a perennial contender, a veteran with over 40 professional fights under his belt, known for his crisp boxing, vicious body kicks, and a no-nonsense attitude born from his street-fighting origins in Miami. Masvidal, often referred to as "Gamebred," was experiencing a career resurgence, coming off a spectacular knockout win over Darren Till and a memorable backstage altercation with Leon Edwards that birthed the legendary "three-piece and a soda" line. He was hungry, focused, and ready to seize his moment, having spent years fighting in various promotions, often feeling overlooked despite his undeniable talent. His demeanor was typically calm, almost menacingly quiet, letting his actions speak louder than words. Then there was Ben Askren, the undefeated wrestling sensation who had just joined the UFC with immense hype. Askren was not only an Olympic wrestler but also a former champion in two major MMA organizations, Bellator and ONE Championship, boasting a perfect professional record. His style was unique: an almost suffocating grappling game that nullified opponents, often grinding them down to submission or decision. Askren was also a master of psychological warfare, an expert trash talker who delighted in getting under his opponents' skin. He had openly dismissed Masvidal's striking, confidently asserting that he would easily take him down and control him, making bold predictions about an effortless victory. Askren's confidence, borderline arrogance, grated on Masvidal, who saw it as disrespectful. The clash of personalities couldn't have been more stark: Masvidal, the humble, hard-nosed striker from a tough background, against Askren, the cocky, undefeated wrestler who seemed to believe his grappling was unstoppable. This dynamic created an irresistible narrative: the pure striker vs. the pure grappler, the veteran contender vs. the undefeated newcomer. Fans were divided, eager to see whether Masvidal's refined striking could keep Askren at bay, or if Askren's "Funky" wrestling would simply overwhelm Masvidal, as it had done to so many others. The intensity of the verbal jabs, Askren's relentless taunting, and Masvidal's simmering intensity all promised an explosive encounter, but nobody could have truly predicted just how explosive that encounter would be, or the seismic aftermath it would create. The build-up wasn't just about fighting skills; it was about pride, respect, and proving who was the superior martial artist, setting the stage for an unforgettable night.

The Unforgettable Five-Second Knockout

Alright, let's get into the money shot, the moment that nobody who witnessed it will ever forget: the Jorge Masvidal vs. Ben Askren five-second knockout. The stage was set at UFC 239 in Las Vegas, an electric atmosphere buzzing with anticipation. Fans were on the edge of their seats, knowing that something special could happen given the intense build-up, but utterly unaware of the sheer, brutal speed with which it would all unfold. The bell rang, signifying the start of the fight, and in that instant, everything changed. Jorge Masvidal, known for his calculated aggression, executed a move that was as audacious as it was brilliant. Instead of meeting Askren in the center for a traditional exchange, Masvidal took a single step forward, paused for a split second, and then sprinted across the octagon, launching himself into the air with a perfectly timed and devastating flying knee. Ben Askren, true to his wrestling instincts, was already dipping his head, aiming for an immediate takedown, probably expecting Masvidal to close the distance conventionally. This split-second decision proved to be catastrophic. Masvidal's knee connected flush with Askren's chin, a sickening impact that reverberated through the arena. Askren crumpled to the canvas, unconscious before he even hit the ground. The crowd erupted, a mixture of shock, awe, and disbelief washing over everyone. But Masvidal wasn't done. He followed up with two brutal, unnecessary hammerfists to the already prone Askren, a controversial move that Masvidal later defended by stating Askren's trash talk had warranted it. The referee, Herb Dean, quickly intervened, waving off the fight and bringing an immediate end to the contest. The official time? A mere five seconds. This wasn't just a fast knockout; it was the fastest knockout in UFC history, a record that still stands to this day. The replays were instantly circulated, played over and over, each viewing confirming the absolute perfection of Masvidal's execution and the brutal finality of the strike. Commentators were speechless, fans were roaring, and the entire MMA world was left in a state of utter shock. The flying knee became an instant legend, a highlight reel staple, and a defining moment in both fighters' careers. For Masvidal, it was the explosive culmination of years of hard work and frustration, catapulting him into superstardom. For Askren, it was a sudden, brutal end to his undefeated run and a stark reminder of the unpredictable, unforgiving nature of the sport. The aftermath of those five seconds would define their respective paths in MMA, creating divergent legacies born from a single, unforgettable moment of violence and precision.

The Aftermath: Divergent Paths Post-Fight

The immediate aftermath of the five-second knockout profoundly reshaped the careers and public perceptions of both Jorge Masvidal and Ben Askren. For Masvidal, it was a slingshot to superstardom, an overnight transformation from respected veteran to bona fide main event attraction. For Askren, it was a moment of profound defeat that ultimately led him to a contemplative, albeit brief, conclusion to his fighting career. The paths they took after that iconic moment diverged dramatically, cementing their individual legacies in the annals of MMA history.

Jorge Masvidal's Explosive Ascent to Stardom

For Jorge Masvidal, the Ben Askren knockout was nothing short of a career-defining event, a moment that rocketed him from a fan-favorite veteran to a true global superstar. Prior to this fight, Masvidal had been a well-respected fighter, known for his gritty style and deep resume, but he often hovered just outside the elite-tier conversations. However, that flying knee changed everything. It wasn't just a knockout; it was a statement. Masvidal's raw, unapologetic post-fight comments, particularly his declaration that the follow-up punches were "super necessary" given Askren's pre-fight trash talk, resonated deeply with a segment of the fanbase. This moment, combined with his earlier "three-piece and a soda" incident with Leon Edwards, cultivated a new, aggressive, and highly marketable persona for "Gamebred."

Suddenly, everyone wanted to see Jorge Masvidal fight. His stock soared like never before, and the UFC was quick to capitalize on his newfound popularity. His next fight was against none other than Nate Diaz at UFC 244, a contest that captivated the entire combat sports world. The UFC even created a special, one-off championship for this highly anticipated clash: the BMF (Baddest Motherf*er) Title. The energy surrounding this fight was immense, culminating in a sold-out Madison Square Garden and a star-studded audience, including Dwayne "The Rock" Johnson, who presented the belt. Masvidal dominated Diaz, winning via doctor stoppage, and solidified his status as one of the sport's biggest draws. This victory, combined with the Askren KO, cemented his place as a legitimate, exciting main event fighter. His path after Askren was one of consistent upward momentum, securing higher paydays, bigger fight opportunities, and a loyal fanbase that adored his authentic, no-nonsense approach to fighting. He went on to challenge for the welterweight title multiple times, faced off against other top contenders, and became one of the most recognizable faces in the UFC. The Jorge Masvidal who emerged after the Askren fight was a far cry from the journeyman he once was; he was a bonafide superstar, forever linked to that iconic five-second moment.

Ben Askren's Reflection and Retirement

In stark contrast to Jorge Masvidal's meteoric rise, Ben Askren's career took a different, more reflective turn after the devastating five-second knockout. Prior to the Masvidal fight, Askren was undefeated, riding a wave of confidence and coming off a controversial win over Robbie Lawler in his UFC debut. The knockout, however, was a brutal, undeniable loss that shattered his perfect record and forced him to confront the unpredictable nature of MMA at the highest level. Immediately after the fight, Askren handled the defeat with remarkable grace and humor, a testament to his character. While Masvidal revelled in his victory, Askren quickly bounced back on social media, making light of the situation and refusing to let it define him.

Despite the significant setback, Ben Askren was still a competitive fighter, and he made a quick turnaround, fighting just three months later against grappling legend Demian Maia at UFC Fight Night 162. This fight was seen as a chance for Askren to reassert his grappling dominance and prove that the Masvidal loss was a fluke, a result of a perfectly timed, anomalous strike. However, in a hard-fought battle, Askren was submitted by Maia in the third round, marking his second consecutive loss. These back-to-back defeats, combined with long-standing hip issues that had plagued him throughout his career, led Askren to make a pivotal decision. In November 2019, just a few months after the Masvidal knockout, Ben Askren announced his retirement from mixed martial arts. He cited the need for a hip replacement, the cumulative damage of a long wrestling and MMA career, and a desire to be present and active for his young family as primary reasons.

Askren's perspective on the knockout remained consistent: it was a moment of bad luck, a perfectly executed strike, but he never let it diminish his overall legacy as an elite grappler and a successful multi-organization champion. In his post-fighting life, Askren remained active in the combat sports world, often providing commentary, running wrestling clinics, and maintaining a popular social media presence where he continued to engage with fans and playfully poke fun at himself, including the infamous knockout. He even made a brief, high-profile return to combat sports in a boxing match against Jake Paul, further demonstrating his willingness to embrace new challenges. The Ben Askren who retired after the Masvidal fight was a man who had achieved great success, faced a dramatic defeat, and ultimately chose his health and family over continued competition, leaving behind a complex but undeniable legacy as one of the most unique and dominant grapplers in MMA history.

The Enduring Legacy of an Iconic Moment

The Jorge Masvidal vs. Ben Askren knockout isn't just another entry in the UFC's extensive highlight reel; it's a moment frozen in time, one that continues to captivate and resonate with fans years later. Its enduring legacy is multifaceted, impacting both the careers of the fighters involved and the broader narrative of mixed martial arts. This isn't merely a testament to Masvidal's incredible athleticism or Askren's unfortunate timing; it speaks to the raw, unpredictable, and often brutal beauty of the sport itself. The fact that it was the fastest knockout in UFC history certainly gives it a statistical claim to fame, but its true power lies in the narrative it created. For Jorge Masvidal, the flying knee was his magnum opus, the definitive moment that transformed him from a respected, gritty contender into a global phenomenon. It allowed him to shed the label of "journeyman" and embrace his true potential as a superstar. His subsequent BMF Title win and numerous main event appearances were direct consequences of the immense hype and popularity generated by that five-second explosion. The image of Masvidal leaping into the air has become synonymous with his brand, a symbol of his "Gamebred" approach and his willingness to take risks. It wasn't just a knockout; it was an artistic statement, a declaration that he was ready for the big time, and the aftermath saw him achieve it.

For Ben Askren, while undeniably a low point, the knockout also cemented his place in MMA lore. Despite being on the receiving end, Askren's dignified and often humorous response to the loss endeared him to many. The moment itself became a viral sensation, leading to countless memes and replays, ensuring that his name, alongside Masvidal's, would forever be linked to this historical event. It highlighted the fragility of an undefeated record and the immense danger that even a pure grappler faces against an elite striker in MMA. The legacy for Askren isn't just about the loss; it's about the entire arc of his career, from his undefeated dominance in other promotions to his brief, impactful, and ultimately challenging run in the UFC. The unpredictability embodied by this fight is precisely why fans are so drawn to MMA. One single, perfectly timed strike can unravel months of preparation, years of an undefeated record, and instantly redefine careers. It serves as a constant reminder that in the octagon, anything can happen, and the margins between victory and defeat can be incredibly thin. The Jorge Masvidal vs. Ben Askren fight will forever be replayed in highlight reels, debated in online forums, and discussed by fans as a prime example of MMA's chaotic brilliance, forever shaping the legacy of both men and providing an iconic moment that continues to inspire awe and discussion.

Conclusion: A Moment Frozen in Time

So, there you have it, guys. The Jorge Masvidal vs. Ben Askren fight wasn't just a fleeting moment of violence; it was a watershed event that continues to reverberate through the world of MMA. That unforgettable five-second flying knee knockout at UFC 239 reshaped the careers of both men in dramatic fashion. For Jorge Masvidal, it was the catalyst for an incredible ascent to superstardom, transforming him into a bonafide pay-per-view draw and cementing his legacy as "Gamebred" with iconic wins and the coveted BMF title. For Ben Askren, while a painful defeat that ultimately led to his retirement from active competition, it didn't diminish his impressive career as an undefeated champion in other major organizations. Instead, his grace in defeat and continued presence in the sport have only added to his unique persona. The aftermath of this iconic moment serves as a powerful testament to the unpredictable nature of mixed martial arts, where one perfectly timed strike can change everything. It's a moment that will forever be replayed, analyzed, and celebrated, ensuring its place as one of the most talked-about and defining chapters in UFC history. It truly was "super necessary" for the legends of both Masvidal and Askren to be written as they were, forever linked by those unforgettable five seconds.