Chasing Checkmate: How a win over Sean O'Malley at UFC 292 would finally tilt the game in Aljamain Sterling's favor

LAS VEGAS — ALJAMAIN STERLING, arguably the best bantamweight in UFC history, casually walks into a downtown apartment complex in phenomenal spirits. He’s about to engage in one of his favorite pastimes — an activity that challenges his mind and resolve unlike anything else. It can play tricks on him, give him a sense of confidence, mere moments before a sudden defeat. It requires him to always be one step ahead and instantly recover from any misstep.

Sterling isn’t about to fight in the Octagon. He’s about to play chess.

“It’s very addicting, man,” Sterling says. “I learned it not too long ago during [the COVID-19 pandemic], and it’s kind of a mainstay for me now. Just playing all the time. Very frustrating, though. It’s a very humbling, frustrating game.”

Sterling (23-3) is scheduled to defend his 135-pound title against Sean O’Malley (16-1) on Saturday in the main event of UFC 292 inside Boston’s TD Garden. The 34-year-old already has the most wins in UFC bantamweight history and will have essentially cleaned out the division after fighting O’Malley. Should he win, Sterling will have beaten four of the top five bantamweights ranked behind him, with the only exception being his friend, Merab Dvalishvili, whom he says he’ll never fight.

Quietly, Sterling has put together one of the most impressive divisional reigns. He is 15-3 since his UFC debut in 2014. Two of those losses came via split decisions against Bryan Caraway and Raphael Assuncao, respectively, that could have gone his way. The third was a knockout loss to Marlon Moraes in 2017, in a matchup he says he took too lightly and greatly learned from. Sterling is 9-0 since then.

There are parallels to Sterling’s career, and his newfound love. In a way, every UFC fighter’s journey is a game of chess — not so much against an opponent, but the games of MMA. There’s so much planning and reacting. Timing, politics, pitfalls and traps. Posturing for specific opponents, dates and opportunities. Planning your next fight is a necessity even before you step into the cage for the one you’re signed for.

Sterling believes he has played the game well. No one can dispute the position he’s in. With a win on Saturday, many expect Sterling to willingly vacate his UFC championship, a move that’s almost unheard of. He would do so to leave it open for his teammate, Dvalishvili, and open the door to a move up in weight, where he would potentially take on the reigning featherweight king, Alexander Volkanovski.

What makes Sterling’s position of strength so remarkable is that he’s played chess on a board that was never really set up in his favor. He’s been given no handouts and has made every move count.

For whatever reason, the UFC has never heavily invested in promoting Sterling. His first featured main event wasn’t until May against Henry Cejudo. Sterling endured a long path to his first UFC title shot, taking on a list of established fighters who had a combined record of 230-46-1. O’Malley, by comparison, has faced irrefutably weaker competition. Six of the eight opponents he’s defeated in the UFC are no longer fighting for the promotion.

This is not to say the UFC has actively blocked Sterling’s rise, but it hasn’t cleared a path for him either. If Boston proves to be Sterling’s checkmate of the 135-pound division, he has more than earned it.

“You look at someone like a Conor McGregor, he played his chess pieces the correct way,” Sterling says. “[But was my board the same as McGregor’s?] Definitely not. I think Conor had a really good chess board. And he had involvement with the UFC. … I think the UFC has viewed me as the lesser [chess] piece that came in and did damage. I’m like the pawn that comes in and attacks the bigger pieces.”

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IT WASN’T always that way. At one point in his career, very early on, Sterling didn’t view himself as a pawn in this UFC bantamweight game. When he made his professional MMA debut in 2011, he saw himself as a king.

Much of that had to do with his personal experience with Jon Jones, the youngest UFC champion and greatest fighter of all time. Jones and Sterling briefly wrestled together in college at SUNY Morrisville in New York. Jones was a catalyst in Sterling’s decision to compete in MMA. Jones, 36, who is two years older, started fighting after his amateur wrestling career and enjoyed immediate success. Within three years, he was already a UFC champ.

Sterling, of course, believed he shared many of Jones’ talents. He started to envision a lightning-fast rule over his division, just like his former collegiate teammate.

“When I came into the UFC, I was a really nice chess piece,” Sterling says. “I had just had three finishes in a row [on the regional MMA scene] and there was kind of a hype around me. I went in thinking I was going to be the next youngest champion. Jones had given me an opportunity to see him train when he got into the UFC. I saw what he was able to accomplish and I was like, ‘I can do something very similar.'”

However, Sterling’s chessboard proved to be much different. He fought tough opposition, of lesser name value than Jones. His wins didn’t pop as much as Jones, who also had the luxury of fighting in a more popular weight class. His losses were more stifling toward his aspirations, as a defeat also meant time off due to injury. Or just being pushed down the pecking order for other rising prospects.

The Jones comparisons wore off and he just became a guy at bantamweight. A talent, for sure, but not a budding superstar champion on anyone’s radar.

And when you’re not a budding star on the UFC’s agenda, it’s easy to turn into a pawn — a sacrificial piece in someone else’s rise. Or a lonely rook, left in the corner of the board waiting to be used. Sterling turned into both after his loss to Moraes. Three of his next four bouts took place on the prelims, and he was in a position where it would take a string of wins to get him noticed again. There would be no lifeline, no quick fight to immediately make him relevant again.

“They’ve certainly never done him any favors,” says Sterling’s longtime coach Ray Longo on the UFC’s matchmaking. “But that’s what I always told him to just keep winning. That’s what he’s there for. He keeps winning, nobody can say nothing to him.”

Sterling strung together four straight wins ahead of his 2020 clash with Cory Sandhagen at UFC 250. In that fight, his first on the main card of a pay-per-view, he choked out Sandhagen in a career-defining performance to earn a title shot against Petr Yan. He infamously won the UFC title when Yan was disqualified for throwing an illegal knee and then upset Yan in an immediate rematch. Saturday will mark his fourth title defense, and a win — which would be the most in the division’s history — would move him into a tie with TJ Dillashaw for the most wins in the division’s title fights.

Although his stature in the weight class has obviously changed, the planning and coordination between Sterling and the UFC have remained fractured.

“They’re still not doing him any favors,” Longo says of the UFC. “Even this fight — he would have liked more time off. He kind of got — I don’t want to say ‘bullied’ into it — but he would have liked to take some time off.”

The UFC declined to comment regarding its matchmaking history with Sterling.

Immediately after Sterling defeated Cejudo three months ago, he called for O’Malley to meet him inside the Octagon. O’Malley was sitting cageside that night, and the two squared off for the cameras. As security pulled them away from each other following a stare-down, Sterling repeatedly yelled one word in the future title challenger’s direction.

“September.”

But at the postfight news conference later that night, UFC president Dana White suggested the fight would “probably” take place in August. When O’Malley was asked for his thoughts on the date, it was like he already knew something Sterling didn’t.

“I don’t think he has a choice,” O’Malley said on Sterling’s preference for September over August. “He doesn’t have a choice. He’s going to fight sooner rather than later.”

I’m a phone call away boss! Respectfully, you made a fight, the night of the fight, without a single word of it mentioned to me or checking on my injuries. I have a personal life outside of fighting. But once again, I’ll show up and piss in everyone’s Cheerios…again.
Cheers 🥂

— Aljamain Sterling (@funkmasterMMA) May 24, 2023

Lo and behold, the UFC announced the title fight would happen in August less than two weeks later. Sterling publicly lamented the quick turnaround, which drew a quick response. “Aljo’s one of those guys that just can’t get out of his own way,” White said regarding the post. Whether Sterling was ‘bullied’ into the August date or not, as Longo suggested, he obviously felt hesitancy toward it.

For the record, this doesn’t mean Sterling is playing a different game from anyone else. It’s still chess. He and O’Malley are playing the same game by the same rules. But think of the board at UFC 292. Is it better suited for Sterling, having to cut weight and fight twice in a span of three months? Or is it better for O’Malley, who is coming off a 10-month layoff, which he’s put to use in preparing for his first shot at a UFC championship?

“We bring it up. It’s motivation,” Longo says. “I tell him winning is the best revenge, and this fight is the best one to go out there and really make a statement.”

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STERLING NEVER HAD any desire to play chess before 2020. He was inspired to learn the game after watching the Netflix series “The Queen’s Gambit” during the pandemic.

In chess, a gambit is when a player makes a sacrificial move — gives up something to his or her opponent to set up a bigger move. It’s fitting that this is what drew Sterling to the game because he views himself as the UFC’s favorite gambit — or perhaps, the gambit that has repeatedly gone wrong. Sterling believes the UFC has used him as a pawn, only to watch bigger his opponents fall.

“I’m like the piece that causes more chaos than it should,” Sterling says. “You kind of think, ‘OK, this guy’s career is probably going to go here,’ and then I come in and just ruin the plans.

“Well, hey guys, I have a Plan B. Here’s my gambit. Sorry to ruin the plans a little bit.”

In Sterling’s mind, he was supposed to lose to Sandhagen in 2020. Sandhagen was a young, exciting, “new” type of fighter, with flashy finishing ability. Sandhagen was one win away from a title shot, and Sterling submitted him in the first round.

After Sterling won the UFC championship in the way he did, no one expected him to be competitive in a rematch one year later. Sterling edged Yan via a split decision

“I know for a fact that first fight against Yan was the worst fight of my entire life,” Sterling says. “So, to have that type of performance and then have a devastating illegal strike become my blessing in disguise to get another opportunity, that was a gambit in itself. To just stick around and long enough, come back and show the world, ‘hey, the joke’s on you.'”

After Yan, Sterling fought former UFC champion and pound-for-pound candidate Dillashaw, who returned from a two-year drug suspension to reclaim the 135-pound title he never lost in the cage. Dillashaw becoming champ again would have been a polarizing, sexy storyline in the UFC, and it would have created plenty of big potential matchups. Sterling ran through him in two rounds.

“‘The big return, daddy’s home,’ storyline,” Sterling says. “Well, daddy’s not home. Daddy’s been here the entire time. Thanks for coming.”

And then Cejudo. The former two-division champion, who came out of retirement and promised to take care of the UFC’s “Sterling Silver.” Sterling outwrestled the former U.S. Olympic gold medalist, en route to another split decision. Immediately after the bout, a visibly incredulous Cejudo’s first words were, “He’s tougher than I thought.”

It’s all led up to UFC 292 on Saturday, when Sterling will take on one of the most popular fighters in O’Malley. O’Malley, 28, has been a darling of the UFC ever since he scored a viral knockout on “Dana White’s Contender Series” in 2017, prompting Snoop Dogg to wildly scream his name over and over again on a guest commentary. O’Malley’s accomplishments are nowhere near Sterling’s, but he boasts more than four times as many followers on Instagram.

Nothing against O’Malley, but the board in which his UFC career has played out looks nothing like the one Sterling has performed on. Sterling has been forced to remove every single one of his opponents in order. O’Malley has legitimate wins, but his path has been undeniably streamlined in comparison.

Perhaps the question now is, Will that change if Sterling wins on Saturday? After having to scratch and claw for every inch of progress at 135, will a direct path open to the king of 145?

Sterling doesn’t like to get ahead of himself. He did that once, and it resulted in the worst loss of his career, back in 2017 to Moraes. His focus is solely on O’Malley. But yes, if all goes well, the 135-pound king will likely start to target the 145-pound king, Volkanovski. And if Sterling were to pull something like that off, it might be the greatest gambit of all time.

“I feel like [featherweight] is just a whole new game,” Sterling says. “I think me going out there and doing what I say I’m going to do [on Saturday] puts me in a really good spot to corner the [featherweight] king, Volkanovski.”