Roundtable: Is Sean Strickland’s stunner over Israel Adesanya the biggest UFC upset ever?

Sean Strickland putting on a complete five-round performance to shut down Israel Adesanya was a surprise, there’s no questioning that. But where does the new UFC middleweight champion’s triumph rank among the greatest upsets in UFC history?

Matt Serra knocking out Georges St-Pierre? Julianna Peña running through Amanda Nunes? A one-eyed (!) Michael Bisping clobbering Luke Rockhold? Strickland over Adesanya is firmly in the discussion, so our panel of Alexander K. Lee, Shaheen Al-Shatti, Steven Marrocco, and Damon Martin sat down to figure out just where UFC 293 belongs on that illustrious list.

Al-Shatti: I won’t lie, dear friends, I’ve spent an inordinate amount of time thinking about this question over the past few days, if only because I feel it’s important to put these type of sport-shattering moments into proper context when they occur. In doing so, I’ve narrowed down a five-point blueprint to help us weigh the significance of all-time upsets.

We’ll call it Parker’s Principles of Five Ps, named of course after the GOAT unarmed combatant Parker Porter, who once beat the odds to last an entire 36 seconds in the cage against some guy named Jon Jones. (Also because I googled for 30 minutes straight only to discover an inordinate lack of P-named underdog success stories throughout history. Look, we’re still workshopping the name. If you think of something, help a brother out. Anyway…)

1. The pre-fight perception: What were the narratives being widely discussed and disseminated before the fight occurred? In other words, just how outlandish did the prospect of Challenger X beating Champion Y feel in the public consciousness?
2. The probability: Simple and to the point — just look at the betting odds. To what degree did the bookmakers whose fortunes ride or die on a bout’s result discount the potential of an actual upset?
3. The presence — or lack thereof — of any weird, unique, or potentially disadvantageous circumstances: Think Michael Bisping accepting the Luke Rockhold rematch on ridiculously short notice after already getting trucked in less than six minutes by the man. (And, you know, doing it all with one working eyeball.)
4. The performance: There is a chasm of difference between a result that could be dismissed as a perfect storm, trip-over-a-banana-peel style fluke — aka Peńa def. Nunes — or a leave-no-doubt domination a la T.J. Dillashaw rising from near-obscurity to outclass Renan Barao for five increasingly overwhelming and impressive rounds.
5. The postscript: How did these two fighters fare afterward? Will history look back on the upset as a great leveling up and/or moment of clarity — Dillashaw is a perfect example; see also: “Huh, Holly Holm is actually pretty good and Ronda Rousey was actually pretty limited” — or will the result remain an aberration that baffles years down the line (ex: Serra def. GSP).

With that being said… boy, Strickland over Adesanya certainly checks a lot of boxes.

Perception? Check. One need not look far to see where the public consciousness sat regarding UFC 293 before the unthinkable played out. Did all of us on this roundtable get it wrong? Sure. But did plenty of minds infinitely smarter than us not even begin to give Strickland a snowball’s chance in Hell to pull off what he did? Absolutely. How about probability? Check. Adesdanya was nearly as high as a 8-to-1 favorite on some sportsbooks. That’s a wild betting line for a UFC title bout — one supplemented by the next bullet point on our list, the fact that Strickland wasn’t even supposed to be here. He was such a deep-in-the-bullpen back-up plan that Israel Adesanya himself had to literally convince the UFC to give Strickland the shot. A superstar champion pleading for the chance to suffer his unlikely fate is as weird of an extracurricular circumstance as you could ask for.

And of course, performance. This one is self-explanatory. As has been repeated countless times by now, this was no fluke knockout. No, Strickland outclassed Adesanya to such an outrageous degree that it made the prospect of a rematch feel genuinely superfluous.

That’s four for four.

Our final factor, postscript, is obviously the big unanswerable. For all we know, Strickland is about to rattle off a few title defenses over A+ competition like DDP and Khamzat Chimaev and be looked back on fondly by history as a Hall of Fame worthy champion. He’s only 32 years old, after all, and is coached by one of the sharpest minds in the sport. Or, one of these top talents at 185 pounds is going to melt him Pereira style, he’ll go back to headlining random UFC APEX shows, and all of this will be remembered as middleweight’s strangest detour into bizarro land. Right now, anything and everything is on the table.

All of which is to say that, after a few days of separation, I’ve landed on a belief that Strickland def. Adesanya is either the third- or fourth-biggest upset in UFC history. Serra-GSP is forever the automatic No. 1 — as crazy as UFC 293 was, it isn’t a journeyman grappler winning a title shot on a dumb reality show then colding one of the greatest fighters of all-time in three minutes. Peña over Nunes remains my No. 2, if only because Nunes is the legitimate women’s GOAT and Peña doesn’t own a win over anyone currently employed by the UFC. But Bisping over Rockhold? Considering how the rest of Rockhold’s career played out once his aversion to left hooks came to light, you could convince me that Strickland’s unlikely method of victory matches the cathartic coronation we all witnessed at UFC 199.

Either way, the fact that this is even a conversation is breathtaking in and of itself.

Photo by Mark Evans/Getty Images

Marrocco: Using Shaun’s helpful checklist, I don’t think there’s any disagreement in keeping Matt Serra as the GOAT of MMA upsets. Only one matter of perception might warrant a second look: As Ariel Helwani helpfully pointed out on Monday’s The MMA Hour, we might be giving Serra too much credit based on St-Pierre’s postscript as a champion. When St-Pierre lost to Serra, it was his first title defense; he was far from welterweight GOAT status.

So if we’re ranking who gets the No. 2 spot, it’s Nunes vs. Peña for my money. Nunes had dominated two whole divisions and was attempting her sixth bantamweight title defense. Pena was a 7-to-1 underdog. Nunes had plenty of time to train, and yet, her performance combined with Pena’s tenacity still led to her complete collapse. Points (imaginary ones) are deducted for Pena’s postscript, a one-sided throttling that convinced everyone her first win was a fluke. But those first four Ps all give the bantamweight fight a strong argument for the penultimate spot.

The tougher question, in my humble opinion, is whether Strickland vs. Adesanya supplants Anderson Silva vs. Chris Weidman 1 as the greatest middleweight upset of all-time. And this is perhaps where my personal bias sneaks in — I give a lot of weight to that first P. It’s what gets most of us watching in the first place. And if you have a dominant champion, of which there is no disputing Silva as the most dominant of all-time at 185 pounds, it becomes all the more earth-shaking when there’s an upset. I know Weidman looked amazing in his run to the belt, and he was not as big of an underdog as others. I just remember how inevitable Silvia’s victory felt, and not until Weidman took advantage of his self-immolation (the clowning bit) was that notion shattered.

I don’t shout at my TV often, but Peña and Weidman? You could hear me from next door.

Esther Lin, MMA Fighting

Martin: Context always matters when talking about something like biggest upset in UFC history.

That’s why it’s almost impossible to dethrone Matt Serra thumping Georges St-Pierre inside one round as the greatest WTF moment of all-time. Serra, who was bounced from the UFC following a meager 4-4 record, earned his title shot by winning a reality show filled with other promotional rejects. It was the most improbable way to get a title shot, much less win it!

For that reason alone, Serra still sits atop that mountain all by his lonesome, but Sean Strickland certainly tried to climb that peak. On my own podcast The Fighter vs. The Writer, my co-host Matt Brown spoke to the chance that perhaps Strickland could pull off something crazy because MMA is so wildly unpredictable, but I actually talked him off that ledge because it seemed like Adesanya defending his belt — even in an Israel-wins-as-he-did-against-Cannonier-or-Vettori style snoozer — was almost a lock.

Boy, did that backfire.

Strickland not only beat Adesanya, he thoroughly defeated and even arguably broke the now former UFC middleweight champion. It was a systematic dismantling. It was like watching Freddy Krueger slice through unsuspecting teenagers, except there was no final girl there to stop him.

But again, context matters, and as impressive as Strickland’s win might be, it’s still not the biggest or best upset.

Michael Bisping’s demolition through Luke Rockhold on 10-days’ notice after he was dominated by the same fighter less than two years earlier was astonishing. Julianna Peña — without a single win over anybody on the current UFC roster — beating Amanda Nunes when “The Lioness” appeared unbeatable still rattles the brain. And perhaps even Gabriel Gonzaga decapitating Mirko Cro Cop via head kick — in a tape-delayed UFC event — still seems more shocking now than Strickland’s inexplicable victory over Adesanya.

Make no mistake, what Strickland did was almost beyond comprehension, and that win may slip into the top five for greatest UFC upsets, but his title shot wasn’t earned off a reality show. He didn’t take the fight on 10-days’ notice. He didn’t beat a GOAT and he didn’t lop the dome off a fighter who literally had his own head kick nicknamed “left leg cemetery.”

For all those reasons, Strickland’s upset was awe-inspiring, but nowhere near No. 1.

Photo by Chris Unger/Zuffa LLC

Lee: Strickland over Adesanya isn’t the biggest upset in UFC history. But the fact that it even has a reasonable case to be No. 1 is astonishing given how I felt about the possibility this same time last week. I’d braced myself for Strickland catching Adesanya with a “puncher’s chance” shot, or Strickland going full Peña for 25 minutes and gutting out a win that way. Nothing prepared me for Strickland straight outclassing Adesanya on the feet.

That matters if we’re playing the comparison game, and in this regard, it stands up well against Serra’s once-in-a-lifetime (literally, Serra had never KO’d anyone before) knockout punch of “GSP” and Bisping turning the tables on Rockhold in their unexpected rematch. As for Peña, her and Strickland were both lightly regarded as contenders before pulling out convincing victories over champions in the GOAT discussion (Nunes more so than Adesanya). An instant rematch like Nunes received, as dull as it sounds, would go a long way toward helping us contextualize what Strickland accomplished.

To that point, we don’t really know what we have with Strickland as far as his potential greatness goes. He’s 15 years deep into his career, which suggests that he is what he is, but if he rattles off two or three title defenses against a frisky group of middleweight contenders (DDP! Khamzat!! Bo!!!) then this Adesanya win becomes more than just a footnote. It becomes the first page of a substantial chapter in Strickland’s legacy.

I can play the Serra-GSP card all day, and I stand by the magnitude of that upset being insurmountable, but that has a lot to do with circumstances and context that cannot be recreated. Based solely on the perceived gap in skill level, the reputation of the challenger, and immediate “wow factor,” there’s a strong case to be made that Strickland didn’t just break our Pound-for-Pound Rankings, he’s carved out a spot for himself at the very top of the all-time upset list too.