Here’s a thought experiment for boxing fans who love a good “what if?” Just like the endless debate about the Trail Blazers passing on Michael Jordan for Sam Bowie in basketball, boxing often accepts outcomes as final. Let’s challenge that mindset. Here are five what-if scenarios from 2019 onward that could have reshaped the boxing world, while comparing them to see decent movies.

What If #1: Teofimo Lopez never lost to George Kambosos Jr., and Vasiliy Lomachenko fought Devin Haney in 2019? Imagine Fight Club meets Sliding Doors. In this scenario, the key decision was two-fold: Kambosos’ upset win over Lopez and the lack of a pre-pandemic fight between Haney and Lomachenko. Picture Lomachenko battling Haney in 2019. Regardless of who wins, the logical next step would be a clash with Lopez. Erase Kambosos’ victory over Lopez, and suddenly, lightweight boxing has a clear path for epic showdowns. Haney’s prolonged series with Kambosos wouldn’t have happened, and we might have seen Haney vs. Lomachenko faster or Lopez at their peaks. Maybe Shakur Stevenson or Gervonta Davis? Instead, the division remains tangled in rematch clauses and star egos, akin to Ocean’s 11 with too many actors refusing to share the spotlight.

What If #2: Anthony Joshua didn’t lose to Andy Ruiz Jr. and fought Deontay Wilder instead? This is The Departed – a single pivotal action changes everything. If Joshua had avoided defeat by Ruiz in 2019, he’d be gearing up for a major showdown with Deontay Wilder. Wilder had just come off a dramatic knockout of Dominic Breazeale and a draw with Tyson Fury, while Joshua, despite some shaky performances, was still the next big thing. Ruiz’s unexpected win made Joshua beatable. If Joshua had won against Ruiz, even narrowly, he and Wilder would have been on a collision course. Instead, Wilder faced Luis Ortiz, lost twice to Fury, and Joshua dropped two fights to Usyk. The heavyweight division shifted from must-see to “What happened to these guys?” with Usyk and Fury emerging as the top guys of the era, not Joshua and Wilder.

What If #3: Canelo Alvarez fought David Benavidez? Think The Godfather Part III of boxing what-ifs. Something people remember, but maybe not fondly. Canelo’s career will reach legendary status just like The Godfather, although the fight against Benavidez might serve as the ending of Godfather Part III to his career. A bout between these two might have solidified Alvarez’s legacy as not just the best of his era but potentially the greatest Mexican boxer ever. Now, it seems that ship has sailed. Canelo, like an aging rock star on a reunion tour, is content fighting whoever he chooses. Benavidez, meanwhile, remains a promising talent without a major test. His losses of the WBC super middleweight belt, once due to the scale and once due to a drug test (a recreational drug), could have paved the way for this fight. Instead, we’re left speculating about what could have been, feeling increasingly indifferent as time passes, much like the anticipation of Lennox Lewis vs. Riddick Bowe – great on paper but ultimately never happening in the pros. The only difference, we got Lewis-Bowe in the Olympics, we never saw Alvarez-Benavidez before. 

What If 3b: Canelo Alvarez Gets Praised for Not Fighting David Benavidez?

Here’s a wild thought: What if the world actually praised Alvarez for not fighting Benavidez as a savvy business move? Think about it. Floyd Mayweather got all kinds of love for stringing out the Manny Pacquiao fight, dragging it through a half-decade of will-they-won’t-they drama, and then cashing in for a record payday. It wasn’t just boxing skill; it was a masterclass in business. Mayweather knew exactly how to squeeze every last drop from the fight, playing chess while the rest of the sport was stuck on checkers.

Now, Canelo? He gets a little bit of that praise, but not quite to the same extent. Sure, he’s got his loyal fans and a fat paycheck every time he steps in the ring, but he’s not getting the same "genius businessman" narrative that Floyd had. Could it be that Mayweather was the pioneer in dragging out fights just as social media was blowing up, giving him that perfect storm of hype? (Side note: remember when Floyd was plugging that “Shots App” during the Andre Berto post-fight presser, labeling it ‘the anti-bullying app’? That was peak Money Mayweather.)

With Canelo, it’s different. Instead of a collective pat on the back for milking the clock on a Benavidez showdown, there’s this sense of bitter indifference.

This is boxing’s version of Heat – two elite talents at their peak, circling each other like De Niro and Pacino at Kate Mantilini’s, yet the fight still hasn’t happened. Terence Crawford and Jaron Ennis in the same ring would be a welterweight fan’s dream. But as thrilling as the matchup sounds, it’s stuck in the usual boxing limbo of “maybe next year” and endless negotiations, or even worse – no talks at all.

On paper, it's a blockbuster. Crawford’s a seasoned 36, a pound-for-pound king, while Ennis is the rising 27-year-old star, hungry for his defining moment. But that age gap makes it feel a little too good to be true, like watching Pacino and De Niro in The Irishman – you just wish it happened a few years earlier. Ennis hasn’t really fought anyone with Crawford’s level of experience, and that’s probably what's keeping this fight from getting made. You know, the whole “he’s got to prove himself first” argument we always hear in boxing.

Still, it's one of those matchups you can't help but imagine. Fans are already salivating over it, the same way they get excited about Vergil Ortiz vs. Ennis. Crawford vs. Ennis has that “now or never” energy. If it just happened, it could define the next era of welterweight boxing. But for now, we’re stuck waiting, hoping it doesn’t turn into another fight that fizzles – making us say ‘what-if.’

What If #5: Kenshiro Teraji didn’t get knocked out? For the hardcore fans, this is the Kaiser Soze of what-ifs. Teraji, a junior flyweight champion with 12 title defenses, was knocked out by Masamichi Yabuki in 2021. Although he avenged the loss in style, that knockout could have had more significant repercussions. Without that defeat, Teraji might have been in line for high-profile fights against Roman “Chocolatito” Gonzalez or Juan Francisco Estrada (yes, he’d move past his ideal weight classes, but it will still be talked about). Instead, it’s like The Usual Suspects ending – leaving us craving more details and wondering how Teraji’s unbeaten status might have affected potential matchups, such as a fight with Jesse “Bam” Rodriguez.