UFC 261: A look back at Jorge Masvidal’s wild journey to title contention through the years

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Jorge Masvidal gets a second crack at Kamaru Usman and the welterweight championship when the two rematch in the main event of UFC 261 from VyStar Veterans Memorial Arena in Jacksonville, Florida on Saturday. There’s also a very real possibility the fight represents Masvidal’s final opportunity to become UFC champion.

Masvidal has one of the most interesting stories in MMA history, fighting in backyards alongside Kimbo Slice before grinding away on the Florida regional scene after turning pro in 2003. Masvidal’s journey took him through the tropical locales of BodogFIGHT, the Playboy Mansion in one of his six Strikeforce fights, Japan’s World Victory Road and the Bellator cage before finally debuting in the UFC’s famed Octagon in 2013.

Along his pre-UFC travels, Masvidal experienced some brilliant highs and stunning lows, but as his career moved along, Masvidal remained a respected, well-rounded talent who could show up any given night and perform like one of the best in the world.

After continued ups and downs during his UFC run, Masvidal finally seemed to achieve his potential in a Fighter of the Year-caliber 2019 campaign, leading to his first shot at Usman, which came on less than one week’s notice at UFC 251 in July 2020.

Now, with a full camp, Masvidal will look to hit the ultimate high of his career by pulling off the upset when he faces Usman with the benefit of a full camp.

This week, Brian Campbell and Luke Thomas took a look back through Masvidal’s career with an in-depth Resume Review on “Morning Kombat”.

Can’t get enough boxing and MMA? Get the latest in the world of combat sports from two of the best in the business. Subscribe to Morning Kombat with Luke Thomas and Brian Campbell for the best analysis and in-depth news.

Let’s take a look at three fights from Masvidal’s career the CBS Sports experts believe to be his top career-defining moments.

vs. Donald Cerrone (Jan. 28, 2017): For as much as Masvidal’s 17-month layoff immediately before his meteoric run to an unlikely fighter of the year honor in 2019 has been given credit for creating the monster within him willing to “baptize” opponents, his victory two years earlier against Cerrone provided an early preview of the fighter he would become. Yes, Masvidal had previously suffered a trio of split-decision losses in the years leading up by not being offensive enough (and would add a fourth such defeat in the fight immediately after Cerrone against Demian Maia). But the full-force offensive attack Masvidal showcased in his dismantling of a red-hot Cerrone was the antithesis of those performances when Masvidal showed technical proficiency yet was too willing to play a counter-striking role that limited his output. Against Cerrone, Masvidal took the fight to his equally rugged opponent, who entered on a four-fight win streak within a run of 12 victories over 13 fights. Maybe even more importantly, Masvidal displayed a marketable and confident swagger in the aftermath of his stoppage defeat that he had previously hidden. Not only did Masvidal get into his opponent’s face to taunt him after the fight, which set off a chorus of boos from the pro-Cerrone crowd in his native Colorado, the negative reaction allowed Masvidal to realize he could revel in it like a pro wrestling heel. It’s a persona he would further develop in the promotion of fights against Darren Till and Ben Askren. — Brian Campbell

vs. Stephen Thompson (Nov. 4, 2017): A pivotal event in the career of Masvidal — arguably, the pivotal event — is his loss to Stephen ‘Wonderboy’ Thompson at UFC 217. Heading into the contest, Masvidal had recently suffered a split decision loss to Demian Maia, but only after going on a three-fight win streak that featured a stoppage win over Donald Cerrone. ‘Gamebred’ might’ve stumbled against Maia, but here was a main card slot in a relevant fight on a monster pay-per-view. In the end, it wasn’t to be. Thompson not only beat Masvidal, but even took a 10-8 round on one judge’s scorecard. The loss not only undid a lot of career momentum, but it would serve as the last fight before an eventual 19-month layoff. It was during this hiatus, however, that Masvidal would sojourn into the literal jungle and ultimately discover himself anew. Upon his return to competition, he ended up as a 2019 fighter of the year candidate on any ballot. — Luke Thomas

vs. Darren Till (March 16, 2019): There are endless great choices for top Masvidal moments, but the fight with Till is where Masvidal activated his final form like a video game boss. Of his six UFC losses at that point, four came by split decision, with Masvidal often simply not fulling kicking his offense into gear and doing just enough to lose. You’d see the potential against a Donald Cerrone or Jake Ellenberger, but then it would be right back to the same old problems. Then, Masvidal took 16 months away from the cage and came back as the B-side to Till, fighting in Till’s backyard of London and almost serving as an afterthought to the UFC’s view of Till as a potential superstar. Masvidal entered the Octagon as an underdog — and with a new look — and things started poorly. Till dropped Masvidal early, poked him in the eye and got the better of almost every striking exchange in the opening round. In the second round, Masvidal landed a bomb of a left hook, sending Till crashing to the canvas for the comeback victory and reminder that he was a truly dangerous man. But it wasn’t only the fight that mattered for the Legend of Masvidal on that night. After the fight, Leon Edwards walked past the victorious Masvidal, dropping some trash talk in the process. Masvidal calmly walked away from an interview with his hands clasped behind his back, telling Edwards to say it to his face “like a man.” Edwards raised his hands into a fighting position and Masvidal cracked him with three punches, cutting Edwards under his eye. Masvidal would later explain that he “gave him the three-piece with a soda,” and a meme was born. Without the win over Till and viral confrontation with Edwards, the world may never have seen Masvidal hit superstar status and go on to the big money “BMF” title fight with Nate Diaz.

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