Few seem to realize it, but Floyd Mayweather Jr. has been chasing Muhammad Ali his entire career. Not that there’s anything unique about that. There has never been another Ali and there never will be, but since his reign countless fighters have sought to replicate his success, his notoriety and his aura.

Mayweather’s latest attempt at capturing a slice of Ali’s glory steers him into the path of former heavyweight champion Mike Tyson, who will be nearly 60 when they share a ring and fight what, for now at least, will be an exhibition match.

On surface level, Mayweather and Tyson are simply adding to the recent trend of exhibitions between fighters whose retirements are either firm or situational. Tyson himself fought one with Roy Jones, which helped boxing feel less barren while neck-deep in pandemic doldrums. And in Mayweather’s case specifically, it’s one more after about a half-dozen exhibitions since defeating Conor McGregor in a pro boxing match in 2017.

In fact, we’ve seen former champions from Marco Antonio Barrera to Evander Holyfield hop into the ring in recent years. Some exhibitions were successful, others nearly disastrous.

For many years, however, nearly every fight was an exhibition. As boxing first developed into a more organized sport in the 18th century, real fights were still very much frowned upon and exhibitions both spread the word about the sport and served as a way to win over a skeptical public.

The rise of vaudeville and carnival circuits around the turn of the 19th and 20th centuries amplified any existing acting already present in boxing. But for professional fighters, exhibitions quickly turned into streams of income that allowed them to circumvent boxing bans. After all, if fighters entered the ring pledging not to inflict real damage, it was enough to sate local bloodlust while avoiding involvement from law enforcement.

In those days, battling jurisdictional legalities combined with a different ruleset and a lack of infrastructure made boxing an entirely different endeavor. Much of the skeleton is the same — it’s still two people punching one another for money, after all — but enough changed that boxing is unrecognizable to older generations.

On the elite level, fighter purses have increased so drastically that fighting exhibitions isn’t even practical for active fighters. The risk of getting cut or injured in an exhibition and having to cancel a bigger-money clash is too great. Perhaps that’s why Mayweather, in a move very reminiscent of Ali, ensured that his exhibitions and bigger-money fights are one and the same.

Heavyweight champions fighting exhibitions is one of the sport’s oldest traditions. Not every champ fought them, but many did, from Jem Mace in the 1870s to Ali in the 1980s. It took Ali, the king of heavyweight kings, to transform his exhibitions into something more captivating.

When Ali was still Cassius Clay, he participated in an exhibition with former champion Ingemar Johansson at the Miami Beach Convention Hall. Ali reportedly did well against the slower Johansson, though the description of the affair read more like a public sparring session.

From the time Ali won the title until 1982, he fought more than 80 exhibitions with a few clear standouts. In 1977, he tangled with future WBA heavyweight champion Michael Dokes and showed off some of his old razzle-dazzle against a young up-and-comer. Ali also clowned NFL player Lyle Alzado in front of a crowd of about 20,000 in 1979.

Ali’s crowning achievement, at least in terms of his sideshows and attractions that departed from straight-up boxing, just might be his 1976 mixed rules bout against Antonio Inoki. The event was like a collision of different worlds, and it ultimately highlighted the most absurd things about boxing and wrestling while still successfully banking off of each man’s popularity by filling an indoor arena, netting Ali $6 million and selling millions of closed circuit purchases. Ali-Inoki also heralded a massive cultural shift in regards to pro wrestling.

Like Ali-Inoki, Mayweather’s tussle with Tyson is an event few asked for or really anticipated outside of those involved. Mayweather last fought a meaningful pro bout 10 years ago, and Tyson 20. From the perspective of a combat sports purist, it answers no questions. And like before, that won’t matter.

In modern terms, Tyson vs. Mayweather in any capacity is pitting two of boxing’s most-searched internet terms against one another. It’s two of sports’ biggest drama magnets sharing a boxing ring. If the essence of hate-watching and clawing at nostalgia could be distilled down into a single event, Tyson vs Mayweather would be it.

Unlike any of Ali’s big exhibitions, this could be one last opportunity for Tyson and Mayweather to either confirm what most believe of them or leave the ring some kind of hero. Ali was an active, albeit shopworn heavyweight champion, while Inoki founded and ran a successful wrestling organization in Japan and competed for decades to come. Depending on the result and the event’s success, this could be what unfairly defines Tyson, and especially Mayweather.

In 1996, just after Mayweather joined a short list of three-time National Golden Gloves champions, he compared himself to Ali in an interview with his hometown newspaper. He won using the same tactics Ali used, Mayweather said.

Mayweather has evoked the name of Ali numerous times since, and often to quickly fling himself upon the pyre of martyrdom. Most notably, Mayweather served a sentence for domestic battery in 2012 and quickly compared his plight to that of “The Greatest,” who was exiled from his post as heavyweight champion and a Civil Rights Era icon.

To be fair, Ali and Mayweather are similarly polarizing figures, and they ascended to heights of stardom few ever experience. Both experienced racism and fought an institution built to defeat them.

This is all without addressing precisely how Mayweather plans to go from his usual in-shape 150 pounds to anything that could handle even an old Tyson, though the lines between exhibitions, sparring, genuine fights and outright farces have been blurred since the beginning. In truth, it may not even matter as long as he shows up.

Mayweather and Tyson are icons from adjacent boxing eras that now feel nearly as medieval and outdated as the boxing from Ali’s time. We know what old Tyson looks like, and it almost stung to watch. Mayweather is now the last hope of reclaiming anything from that time, even if only briefly.

For him, it’s a last shuffle after the shadow of Ali.