(Editor’s note: This story first published on Oct. 29, 2019.)
UFC 244 on Saturday will feature two fan favorites, Nate Diaz and Jorge Masvidal, throwing down for the title of “Baddest Mother F*cker.”
It started out as a respectful callout between gangsters, but the UFC promotional machine has gotten behind this matchup and taken it to a whole new level. Aside from creating a custom belt for the occasion, there’s the N.W.A. “Straight Outta Compton”-themed poster and “Grand Theft Auto”-inspired video promos. Although I’ve already expanded on my thoughts about the UFC’s crossover into Quentin Tarantino’s universe, I thought it might be fun to focus on the “gangster” element of Diaz’s callout, ranking my favorite gangster moments from their careers.
Without further ado …
****
10. ‘I don’t know what kind of f*cking show this is, man’
Diaz has to be at the top of the proverbial mountain with Derrick Lewis when it comes to post-fight interviews, but his in-octagon interview with Jon Anik after topping Gray Maynard in 2013 is still my favorite from Stockton’s finest.
Diaz starts off the interview with a quote that I saw fit to lead this pick off, opting to ignore Anik’s initial question by voicing almost aimless displeasures with the production to start off his victory lap. Then, in typical Nate fashion, Diaz starts in on his usual laundry list of shoutouts, listing off every name from Ronda Rousey to Chis Avila.
In fact, as someone who was in attendance, Rousey and a huge Diaz contingent were uncharacteristically allowed to form cageside while the younger Diaz brother went on to hold court, proclaiming Gilbert Melendez and himself as the best lightweights in the division (doing everything but sparking a joint up to celebrate). And when Anik asked if he could quickly take us through the finish, Diaz plainly replied, “I won. That’s what’s up,” as he closed with, “I’m hungry. I got sh*t to do.”
It was a pretty gangster moment, if you ask me, but it was also a precursor of post-fight moments to come.
Check it out:
9. Masvidal vs. Ray
Better known as “Ponytail” back in his backyard brawling days, Masvidal would start to put some respect on his name the fateful day he stood up to face Kimbo Slice’s protege, “Ray.”
An excited Ray, who initially knocked out a large corrections officer in just 15 seconds in a fight prior, apparently shouted, “Who wants to run it now?!”
And sure enough, Masvidal stepped through the audience and offered up his hand to scrap. Masvidal, as seen in the video above, was already composing himself as a veteran fighter, staying technical and crisp with his striking. Masvidal even gets dropped at one point, however – akin to a lot of his MMA fights – he composes himself and comes back to pour it on for the win.
Ray would call for a rematch, claiming that he was at an unfair disadvantage because of the fight he had prior. But Masvidal – who warned Ray it would go the same way – kept his word by replicating the result.
“All I have in this world is my balls and my word, and I don’t break them for no one.” – Tony Montana
8. Slapping your boss
It’s something we’ve all probably wanted to do a time or two in our lives, but Diaz actually did it. He actually slapped his boss in the face.
Not only that, but Diaz did this during a time of massive uncertainty – back in 2016 while UFC president Dana White was trying to get both Conor McGregor and Diaz to the table for a rematch following the chaotic outcome of UFC 196. It was just a month prior when White reportedly left a negotiations meeting with the younger Diaz brother displeased, so seeing this image not only erupted social media timelines, but also portended the rematch with McGregor and, perhaps, told us a little bit more about the bargaining power of everyone’s favorite “needle mover.”
White would later claim on an episode of “UFC Unfiltered” that the slap was his idea, but it’s hard to argue who came out the A-side in that equation.
7. McMasvidal
As a man who admittedly makes poor food choices on the regular, I find myself unabashedly rooting for any fighter who can challenge the healthy norms of their professional field and still largely outperform their peers.
B.J. Penn was one of MMA’s most notable repeat offenders who – despite never missing weight – was well known for his penchant to eat like a maniac in and out of training camps (though the UFC Hall of Famer may have to relinquish yet another record once you see Masvidal’s routine in the video posted below).
What I love most is how Masvidal offers up a psychology and philosophy about his eating habits, almost speaking to the enablers in all of us who’d love to find an excuse to eat our favorite dessert for breakfast or go through a drive-thru with the ecstasy and ignorance of a 5-year-old. I also love that this video was shot during his days at lightweight, as I can only imagine what Masvidal is up to these days.
This may seem like a weird qualifier for a list of “gangster moments,” but any man who can eat McDonald’s and compete like Masvidal is a gangster in my book.
6. Light it up
The unfortunate part of carrying the stereotype of a gangster is the baggage that can come with it (especially if you do unfairly stereotyped things like smoke marijuana).
Both Diaz brothers have had issues related to their enthusiasm for cannabis, whether it was one of Nick’s positive tests with the Nevada Athletic Commission or Nate’s U,S, Anti-Doping Agency warning for vaping CBD oil after his rematch with McGregor at UFC 202.
Thankfully for the Diaz brothers and marijuana lovers alike, state laws – as well as agencies like USADA – seem to be steadily following suit with public opinion, loosening up regulations and punishments while they step closer to understanding a plant that grants many positives to the athletes they’re claiming to protect. And now, in the year 2019, you can find Nate lighting up his own brand of CBD cigarettes (offered by Game Up Nutrition line) at a UFC open workout, unmolested by U.S. Anti-Doping.
“You know what’s crazy to me, the best part about this whole thing is … I got kicked out of school for fighting and selling weed. And now for a professional career I’m fighting and selling CBD.”
5. ‘Gamebred’ invades Denver
Although hardcore MMA followers have long-hailed the skills of Masvidal and his once-underrated resume, the man who calls himself “Gamebred” would further emphasize his late-career renaissance by setting his sights on Donald Cerrone in his hometown of Denver.
Entering enemy territory with only his striking coach Paulino Hernandez by his side, Masvidal came into the fight with the odds against him (closing as an underdog). But despite the pre-fight promotional footage showing him jogging in the snow sporting Timberland boots and a trapper hat with a coach who resembles Balki from “Perfect Strangers” by his side, those in the know knew not to be fooled by the almost-disarming tactics of Masvidal.
And come fight night, Masvidal stormed Cerrone’s castle, stopping him in the second round. Sure, the fight probably should’ve been stopped at the end of the first frame, but I couldn’t help but be struck by a cold but cool Masvidal, who casually strolled up to Cerrone to say, “Now you know who I am,” as if he were MMA’s Frank Nitti, letting the best in the division know that they were all “touchable.”
4. Double birds for Batman
There are so many fun memories from my favorite UFC Fight Night card of all time (UFN 13), but how can anyone forget Diaz’s submission win over Kurt “Batman” Pellegrino in 2008?
For those who don’t remember, Pellegrino was a rugged, respected UFC lightweight who came from a wrestling base and carried a black belt in Brazilian jiu-jitsu. But a young Diaz ( who was still a Brazilian jiu-jitsu brown belt at the time) rose to the occasion after a tough Round 1 that saw him crucifixed and cut open by elbows, as he would lock up a triangle choke immediately after being slammed to the mat.
Diaz’s long legs and hard angle allowed him to secure the choke without the use of his arms – which were being preoccupied at the time by his optimization of the production’s overhead cameras, flipping off Pellegrino and the rest of the world via a UFC broadcast (something he tried to replicate later in his title fight at UFC on FOX 5, albeit it to lesser success).
Nevertheless, this was certainly Diaz at his best:
3. ‘Scarface’ lives
The Reebok era makes it difficult for UFC fighters to make statements as they walk to the octagon, but Masvidal’s “Scarface” walkout might be my favorite ring entrance of the organization’s current crop (with respect to Jim Miller and Rafael dos Anjos, of course).
Masvidal is more of a gangster than the fictional character of Tony Montana and is more Cuban than Al Pacino, so taking on the theme from the South Florida-based film makes all the sense in the world. Hell, even the YouTube comments section of the official Scarface theme song (posted below) has been flooded by Masvidal supporters, claiming a new king of the South Florida scene.
Genghis Con Films did a great job capturing the Scarface-feel of Masvidal’s aura in the opening of “The Diaries of a Street Fighter part 2,” as perhaps he really is the second coming of Tony Montana.
2. ‘I’m not surprised, motherf*ckers’
You can make the argument for this being No. 1, but it’ll settle for No. 2 … barely.
Diaz was always a loveable, standout character who can technically hang and scrap with the world’s best fighters, but inconsistencies inside the octagon and politics outside of it always seemed to stifle his shine. However, as fate would have it, an unlikely European counterpart would end up giving Diaz a chance to rise out from the working class at UFC 196.
Taking the fight against Conor McGregor on less than two weeks’ notice and being projected as a more than 3-1 underdog, Diaz was able to, once again, weather the storm en route to a bloody-faced upset that saw him hit his standard Stockton flex for the cameras after unseating the sport’s biggest star. And when Rogan asked him what his thoughts were after shaking up the world, Nate simply replied, “I’m not surprised, mother f*ckers.”
1. ‘3-piece and a soda’
Maybe this is an obvious choice for No. 1, but I couldn’t help myself here.
Not only does Masvidal, once again, go behind enemy lines to knock out a hometown hero as a moderate underdog, but he also finds time to settle a beef backstage with fellow welterweight contender Leon Edwards.
Edwards, who was also coming off a victory in London that night this past March, ambled by Masvidal backstage to call for a July meeting between the two, but Masvidal – who was in the middle of an interview with Laura Sanko – decided to sort it out then and there.
Masvidal would casually stroll up to Edwards with his hands behind his back (which we now know is a tell-tale for violence), unleashing a set of strikes that he would later coin as a “3 piece with the soda.”
Now, I’m not trying to condone or promote violence outside of the cage with this selection, but I couldn’t deny MMA’s version of “When Keeping It Real Goes Wrong” it’s proper due.
