Forgive me for sounding like Panama Lewis as he sized up Luis Resto’s gloves, but: There’s a lot to unpack here.

(It’s been 43 years; I think it’s OK to make tasteless Panama Lewis jokes at this point.)

Let’s start with the unretirement of Mayweather – and the presumably related ongoing reports and rumors that it is no longer fitting to call him “Money.”

Many of those details can be found in a Business Insider article published this past December 28. If Business Insider’s reporting is accurate, Mayweather, the only boxer ever to have made more than $1 billion in gross fight earnings (estimates range from $1.1 billion to $1.5 billion), appears to be out of money.

Or worse.

The article offers numerous instances of debts owed and payments defaulted. And if anyone was left unconvinced by that article, we now have the circumstantial evidence presented by the headlines Mayweather has made in 2026: He sued Showtime and Stephen Espinoza for at least $340 million nearly a decade after he stopped working with them, and he has decided to fight 59-year-old Mike Tyson in an exhibition and then resume his pro boxing career after what will have been about nine years between sanctioned fights.

Whatever the exact extent of his financial troubles, Mayweather, who made more money than most of us could imagine spending in 10 lifetimes, now finds himself in pursuit of more cash and turning to the one line of work he’s always been able to rely on to generate it.

And while this is clearly a problem of his own making, I do find myself feeling a degree of empathy over his situation. He grinded his way from the bottom to the very top of the world and now must begin the grind all over again, whether his body is still up to the grind or not.

You don’t have to feel bad for him. But it’s hard not to feel sad for him.

Mayweather’s career featured its share of short-lived, unserious retirements, the first coming after he TKO’d Ricky Hatton in 2007 at age 30, but he was serious about it when he walked away after decisioning Andre Berto in 2015 at 38. Then the lure of the easiest of easy money pulled him out of retirement in 2017, when he was 40, to play around with Conor McGregor.

And that was it.

There were lots of exhibitions, where the 50-0 record was not on the line, where Mayweather could again enjoy the spotlight, where he could make some more of that easy money – whether he needed it or not.

Now, following the planned April freak show/creak show against Tyson, Mayweather apparently will be putting that 50-0 record at risk.

His first official fight back will be a rematch against Manny Pacquiao, who, like Mayweather, was retired long enough to get inducted into the International Boxing Hall of Fame, but has since returned to the prize ring. Because in boxing, no one is ever really, truly, all-the-way retired.

Which brings us to Crawford, and the second unexpected twist referenced above.

“Bud” Crawford was born 10 years and seven months after Mayweather. He was a month shy of turning 30 and was newly the undisputed junior welterweight champion of the world when Floyd fought McGregor. He was in the conversation for best pound-for-pound boxer on the planet at the time and remained in that conversation – often the central figure in it – over the next eight years, as he claimed titles at 147, 154 and 168lbs and just kept winning and winning and getting bigger and bigger and better and better.

When he scored a unanimous decision over Saul “Canelo” Alvarez last September on Netflix to become a five-division champ and a more recognizable mainstream star than ever before, to secure his standing not just as one of the best of his era but as one of the greatest ever, somewhere in the same rarefied air as Mayweather, the 38-year-old Crawford looked around and saw no worlds left to conquer.

I believe his retirement announcement was sincere.

It remains anyone’s guess whether it will stick.

Occasionally, a fighter retires before he’s undergone significant decline and stays retired, but even then, there is usually a flirtation with the idea of returning. Wladimir Klitschko was speaking publicly about the possibility last year. Joe Calzaghe went in and out of considering a comeback. Andre Ward still brings it up from time to time.

The point is, Crawford may legitimately believe he’s retired, and he may in fact stay retired, but boxing history says the odds are against that, and boxing history at the very least says he isn’t done thinking about fighting and will listen to offers.

And that brings us to the third unexpected twist. Because if there is one singular fight that will force Crawford to at least pick up the phone, it’s an intergenerational clash with Mayweather.

Mayweather’s 2015 fight against Pacquiao sold a record 4.6 million U.S. pay-per-views. Mayweather-McGregor did about 4.3 million.

If promoted properly, Mayweather-Crawford could generate similar numbers – numbers that would be at least double what I believe any other fight in 2026 could produce.

Mayweather-Pacquiao II this September will be on Netflix, not pay-per-view. But if it were to be a pay-per-view, I expect it would struggle to hit one-quarter as many buys as it did in 2015. It’s purely a big-name nostalgia play, not a serious sporting event with anything of value on the line, other than Mayweather’s zero.

Maybe Tyson Fury vs. Anthony Joshua will happen this year or next, but with six defeats now between them, the window for that to qualify as a global superfight has closed.

Canelo vs. Jake Paul? A major mainstream event, but not as major as it would have been had Paul not already lost to Joshua.

Mayweather vs. Paul, a “revenge” fight for Jake since his brother Logan faced Floyd in an exhibition in 2021? Another marketable curiosity that would have been a bigger deal if Joshua-Paul hadn’t already happened, and another fight that would attract customers on pay-per-view but probably not multiple millions of them.

Mayweather vs. Crawford exists on a different plane. It firmly plants one foot on each side of the line between real fight and circus sideshow. It appeals to the boxing hardcores, to the mainstream casuals and to the freak-fest fly-ins.

Could a 49-year-old Mayweather possibly compete against a 38- or 39-year-old Crawford? Logically and chronologically, the instinct is to say no. But until we’ve seen the man who calls himself “TBE” (The Best Ever) look washed up in the ring, there will be grounds to convince ourselves he’s not washed up.

What we’d have here is a 50-0 former pound-for-pound king against a 42-0 former pound-for-pound king, perhaps the two finest fighters of the 21st century squaring off for supremacy, putting those perfect records on the line.

If it’s framed as an exhibition, the needle might quiver moderately. If it’s positioned as an actual fight that counts on their BoxRec pages, Mayweather vs. Crawford makes the needle breakdance.

Sure, as an athletic contest, it would have been more telling and compelling when Crawford was 30 and Mayweather was 40. Mayweather’s age introduces eye-rolling to the proceedings, no doubt.

But his age also serves as a rallying cry for fellow middle-aged men and women. George Foreman insisted 40 was not a death sentence. Bernard Hopkins stunned viewers by remaining championship-caliber at 50. A 49-year-old Mayweather could be an avatar and an inspiration while he simultaneously contends with becoming a cautionary tale.

And think of all the people who helped make Mayweather rich by paying hard-earned money fight after fight in the hopes of seeing boxing’s egomaniacal supervillain surrender his perfect record. They won’t just accept that as a sunk cost and move on.

If Floyd is going to get in the ring with Crawford and potentially get stomped and slip to 50-1 – and therefore never again be able to concoct some sort of argument that he’s better than Sugar Ray Robinson because only one of them ever lost fights – what Mayweather hater alive would allow himself to miss that?

The businesspeople who could put forth a fight like this would make Crawford an offer he can’t refuse. Bud is retired today, but for this money and this opportunity, I am all but certain he would put himself through one more training camp.

It’s the Mayweather side of the equation I’m far less confident about. The zero on his record is an enormous part of his identity.

But a singular zero in his bank account – rather than the string of zeroes he got used to – can shift a man’s priorities.

I have no doubt that the overall game plan behind this return to actual, sanctioned bouts for Mayweather involves a very careful risk-reward calculation and a desire to make as much money as he can without putting himself at serious risk of defeat or injury.

The Pacquiao rematch fits that description. Pacquiao’s seemingly impressive draw against Mario Barrios last year got a lot less impressive when Ryan Garcia dominated Barrios this past Saturday night. Mayweather will be a solid favorite over Manny.

So maybe he can make something like $50 million or $75 million, improve to 51-0, get in, get out and learn to live a lot less large and make the money last.

But if he’s desperate enough, perhaps $250 million or so for one night’s work – in the same vicinity as what he made for the first Pacquiao fight and the McGregor fight – covers the emotional cost of seeing the number “1” on the right-hand side of his record.

I’m not saying I expect Mayweather vs. Crawford to happen.

I am saying it’s plausible in a way it never was before.

For the last eight-plus years, one of these men was an active professional boxer and the other was not, and the two of them squaring off wasn’t really a consideration. But now the performers have swapped roles. The older man is the active fighter, and the younger man is the retired fighter. The entire equation has changed.

And it’s suddenly the biggest, richest fight anyone can envision, and nothing else – not even May-Pac II – comes close.