The Question: Can Conor McGregor Versus Floyd Mayweather Actually Happen?

Brandon Magnus/Zuffa LLC/Getty Images

Like a cockroach that just won't die, the oft-discussed Floyd Mayweather (49-0) versus Conor McGregor (21-3) fight was once again pitched to the public on Saturday. On both sides of the Atlantic, McGregor in a pay-only media appearance and Mayweather on Showtime/SkySports, the principles took their case to the people in stereo.

"I have my eyes on one thing right now, and that's Floyd Mayweather," McGregor told MMA Fighting's Ariel Helwani during a pay-per-view interview in Manchester, England. "That fight is more than just being explored. There's a lot of steps, but it's the fight to make. It's the fight I want."

Mayweather echoed those sentiments in a Sky Sports 1 interview before the Carl Frampton vs. Leo Santa Cruz fight in Las Vegas.

“That’s the only fight that will get me back in the ring," the retired boxer, who has applied for several trademarks related to a potential 50th professional victory, told the world.

And, while the dueling interviews generated headlines, obstacles to the fight remain firmly in place. Though they seem similar, there are significant structural differences separating boxing and mixed martial arts that might torpedo this fight before discussions ever really get started.

Can this fight really happen? And, perhaps more importantly, should it? Veteran reporters Josh Gross and Jonathan Snowden have spent years digging into the financial realities of combat sports, and join forces to tackle one of the most compelling questions plaguing modern fight promotion.

Josh Gross: Is there any quibbling with the notion that nothing is impossible in the fight game when enough money is involved?

Acknowledging the various contractual and regulatory differences between the way boxers and mixed martial artists go about their business, and the problems that oil-water mix could present in seeing this through, the answer is yes this spectacle can really happen because many millions of dollars at stake.

If Mayweather Promotions in conjunction with McGregor Promotions in conjunction with the Ultimate Fighting Championship can actually make it work at the negotiating table, that alone will be a feat.

The potential of massive gate receipts and obscene pay-per-view revenue are the only reasons this is even in discussion, of course.

We know it's not about competition or legacy or proving a point; it's a straight cash grab that will likely entice many, many people in the end. It will also expose a new set of hurdles that could cause it to fall apart because overseeing Mayweather-McGregor will require regulatory chutzpah.

Inherent issues of health and safety are at play, just as they would be if roles were reversed and an inexperienced Mayweather was coaxed into a cage against the Irishman.

On its face an all-time great boxer taking on a fighter whose talent and success as a mixed martial artist has netted him an 0-0 record in the ring would be a non-starter.

But, money.

If, for example, Nevada, California or New Jersey refuse to regulate the contest, where besides an offshore barge could the vested parties take the fight and not become a punchline? There are many risks here, Jonathan.

Which roadblocks (financial, regulatory or otherwise) could end up the promotion killer, and is it appropriate for this to be attempted in the first place?

Jonathan Snowden: I think the biggest road block should be McGregor's lack of anything resembling professional boxing experience. Like Mayweather or not, he's an extraordinarily gifted pugilist. Allowing him to fight a novice, even a famous one, is reprehensible and dangerous.

Then again, as you say, money tends to talk loudly enough to drown out decency and sportsmanship. Nevada, the best of a dodgy lot, allowed Muhammad Ali to fight long after it was clear he was deteriorating badly. The money here is big enough that regulators will cast their eyes down and live with it.

The real problem will be money. More specifically, it will be UFC's involvement in the process. If McGregor was a free agent (or a boxer), I believe they would easily come to terms on an arrangement that would make the rich much richer.

But, believe it or not, the boxing business is built on minuscule margins. When Mayweather fights, there is very little room for promoters to wet their beaks. The bulk of the revenue, from pay-per-view, to foreign television and concessions is shared by the fighters. The promoter can do well if the event is a success—but the top fighters are always going to walk away with most of the money.

As you reported at ESPN years ago, UFC runs a very different system, using a business model based closely on the WWE's. The UFC pockets almost all of the revenue, sharing less than 20 percent with the fighters.

That leaves a gulf filled with tens of millions of dollars separating the UFC from Mayweather's expectations. While a top boxing star can command upwards of 75 percent of the revenue, sources say Mayweather's split is closer to 90 percent. That doesn't leave much room for his own promoter to present a decent undercard and still make money. It leaves no space for UFC to insert itself into the event.

These are basic, systemic problems. If they are to be overcome, someone will have to bend. No one involved is used to that. Who, Josh, do you think is most likely to show some flexibility for the sake of the spectacle?

Gross: 1) Dana White. 2) Conor McGregor. 3) Floyd Mayweather.

The UFC is already bending in ways it never would for MMA, such as making an "official" money offer through the media. Why? The new regime needs to hit big earnings figures the next 18 months to meet "earn-outs," the first of which would pay $175 million in June if UFC increases its revenue by 61 percent from the year before. That means it needs to make $275 million compared to $170 million it produced EBITDA from 2015 to 2016. There's another $75 million waiting for bigger growth in 2018.

So yes the UFC has a ton of incentive to latch on to Mayweather-McGregor because it would be expected pull in the public and generate huge business, the first billion dollar fight. Even a smaller piece of that take than its usual haul from MMA contests puts the UFC in a great spot. It hold some chips, including no small thing in contractual control over McGregor's ability to compete in unarmed combat for money.

There is risk, though, because of the stark differences of the two businesses you spelled out, a potential rift with its biggest star if it gets in the way of the Mayweather fight, butting up closely to the Muhammad Ali Boxing Reform Act, and the potential that McGregor puts his high-flying MMA career in peril by engaging in this boxing bout.

McGregor has always been a risk taker. Anyone who commands so much has to be. He'd easily come down from his early $100 million demands to get the payday and exposure. He risks putting himself through humiliation and potential physical damage for the prospect of boxing Mayweather, but like Muhammad Ali that's part of what makes him who he is.

White meets with Mayweather in 2014.Ethan Miller/Getty Images

Last is Mayweather. Unless he's been negligent with his career earnings, he shouldn't need another payday. But he wants that big number, and feels like its owed to him. This is the man who appears intractable in this equation. Mayweather wants that 50-0? OK. Getting it on 0-0 McGregor doesn't say much about his competitive drive. I suspect if it doesn't happen Mayweather will laugh about the time he screwed around with these UFC clowns, including the guy who carried his bags.

Add in the flexibility of a regulator like the state of Texas and the attractiveness of hosting at Jerry's World and you've got the makings of an extravaganza on your hands.

Then what? Tell me this: After the opening bell how long will it take set in that the fight was a bad idea?

Snowden: It wouldn't take long for onlookers, and likely McGregor himself, to realize he'd made a terrible mistake. While he's shown precision and power in the UFC cage, the skill and expertise of a top professional boxer is unmatched in the realm of combat sports.

Mayweather's dazzling footwork, timing, speed and uncanny instincts would make life exceedingly difficult for McGregor from the very beginning of the fight. Everything, from the ring to the range would be different, including gloves literally twice as big as the ones McGregor wears in the UFC Octagon.

Martial artists initiate attacks from long distances, the threat of a kick or takedown opening up opportunities that simply don't exist in boxing. A disciplined fighter like Mayweather would shred any such attempt to pieces. While not known for his power at 147 pounds, he would land the kind of clean punches that leave a lasting presence. Nate Diaz, a much less gifted boxer, gave McGregor fits, often easily countering his wild blows with punches that accumulated quickly.

In some ways, this fight reminds me less of a traditional athletic contest and more of a spectacle Josh in intimately familiar with. While the stakes and the prize money will be higher, this fight would be more Muhammad Ali vs. Antonio Inoki than it would be Ali's epic matches with Joe Frazier.

Muhammad Ali versus Antonio Inoki.Uncredited/Associated Press

It's easy to see the allure of this fight, especially for Mayweather. For him, it's an enormous pay day with a minimal risk. It's the UFC and McGregor who should pause to consider the implications.

For Conor, an embarrassing performance may further dent a reputation that was scuffed after a loss to Diaz, a fighter who was seemingly settling into journeyman status. It's hard to sell a fighter as cool, brash and cocky when the world has seen him swing hopelessly at air for 36 minutes.

UFC would have even more to lose with such a bout. Not only does it risk the reputation of its top star in a fight that seems all but unwinnable, it also puts the company's hard earned pay structure at risk. Allowing McGregor to call the shots and upset the apple cart invites other to do the same. It's a gamble that only makes sense if the company truly believes McGregor can win and that it can control his rights in the ensuing chaos.

The UFC's $4 billion asking price made sense when it was a promotion with a carefully controlled pay roll. Opening that Pandora's Box for a one-time jack pot against Mayweather is reckless in the extreme. UFC President Dana White is a gambler, but beyond the blackjack table he's also a winner. From the revenue to result, this is Mayweather's fight to lose—and that's why White will never allow it to happen.

Gross: I'm not nearly as confident as you that the UFC can pass up collecting a cut of Mayweather-McGregor. Generating blockbuster money is all that matters to the new ownership right now, and this easily is the biggest spigot they can open at the moment.

If it goes the way the fighters want (all they seem to care about is the same thing the UFC cares about), few people among the many who pay an exorbitant sticker price to watch will pick Mayweather to lose against this wild Irishman.

Here lies the only bit of charm that comes with the idea of this contest: Based on McGregor's profound track record in big moments anything can happen.

Mystic Mac calls out Mayweather, and somehow engineers it into a reality? If he can manage to do that, why can't McGregor go the distance? Or gives the crowd a glimmer of something miraculous when a left hand meets its mark?

That's the fairy tale people will buy if this falls into place, which remains fantasy enough.

Jonathan Snowden and Josh Gross cover combat sports for Bleacher Report.