The Question: Will Conor McGregor Fight Inside the Octagon Again?

The chatter won’t seem to die down, but this time it seems to have some teeth. After on-again, off-again, (now on-again) discussions, the Conor McGregor vs. Floyd Mayweather Jr. boxing spectacle seems to be closer than ever to becoming official.
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The chatter won’t seem to die down, but this time it seems to have some teeth. After on-again, off-again, (now on-again) discussions, the Conor McGregor vs. Floyd Mayweather Jr. boxing spectacle seems to be closer than ever to becoming official.

Just a few days ago, fighter and podcaster Chael Sonnen, who has offered plenty of inside information in the past, said he’s confirmed with industry sources that the fight is a go.

Still, nothing is confirmed, even if we all know that Mayweather wants it, McGregor definitely wants it, and the UFC would be happy to take a (larger-than-deserved) slice of the action.

In fact, just about two weeks ago, UFC President Dana White told UFC minority owner Conan O’Brien that he thinks the fight will eventually be agreed upon.

“I do think it’s going to happen,” he said. “I think it’s going to be a tough deal. There are obviously a lot of egos involved in this deal and a lot of people, so that always makes it tougher. But on the flip side, there’s so much money involved. I just don’t see how it doesn’t happen.”

While agreeing to the money split has been a laborious process, it seems like we’re past the point that any of the parties involved will be able to turn around and reject the pile of cash coming in their direction.

This marks a major turn of events from the original belief that such a bout could never happen. And I must admit that I have been a skeptic for a long time. For a while, it seemed ridiculous that the UFC would potentially offer up one of its biggest ever stars for a possible thrashing, simply in exchange for a short-term cash infusion. Such a decision seemed pound-foolish and penny-wise. And in some ways, it still does. But here we are.

So, now, as we start to accept the likelihood that one of boxing’s greatest ever will fight a rookie to the sport—and that this somehow will become one of the sport’s biggest money generators—it’s time to wonder what this means for McGregor’s future in the Octagon.

Joining me to discuss is my colleague and MMA Lead Writer, Chad Dundas.

Mike Chiappetta: Chad, if a year ago, we’d been sitting in a bar chitchatting and you asked me if this fight could ever actually happen, I would have sighed, ordered another drink and lectured you about the UFC’s iron-clad fight contracts until you drowned yourself in bourbon. 

Now, it seems like it’s inevitable. Mystic Mac saw the future again, and he’s about to make a fortune. Like, a real fortune. Tens of millions. Goodbye-and-you’ll-never-see-me-again kind of money.

If he wants. 

At 28 years old, McGregor will generate the kind of payday that may make anyone question whether they ever need to work another day in their lives. 

Could that possibly happen? I say no. I think that someone that is so infatuated by material things isn’t going to get out of the moneymaking business at such a young age.

Much more possible is that he takes a lengthy break afterward, because, well, why wouldn’t you? His life has been a whirlwind over the last few years. From welfare to multimillionaire, two UFC championships, a multiple world promotional tours, impending fatherhood. 

On top of that, here comes what will without a doubt be the largest payday ever earned by a mixed martial artist (albeit in another sport, but that’s another column entirely). Can you imagine the promotional work and training that will go into it? 

For sure, he is likely to need a break at the end.

For me, my question isn’t about so much about whether he fights again—I believe he will lose to Mayweather, and won’t want to end his story in such fashion—but about what it will do to him. There’s a famous quote by the legendary boxer Marvin Hagler about it being hard to train when you wake up in silk sheets.

This affliction hasn’t affected McGregor yet, but fame and money are still fairly new to him. As those two life-changing phenomena continue to permeate his everyday existence, you have to wonder if the exhausting amount of work necessary in a multidisciplinary sport like MMA will wear on him.

Chad, what do you think? Do you think McGregor takes the money and runs? And if not, what kind of challenge would pull him back into MMA? A third world title, a trilogy fight with Nate Diaz or something else entirely?

Chad Dundas: You certainly make some compelling points here, Mike. As you noted, McGregor is still pretty young (he’ll turn 29 in July) and seems so infatuated with the finest things in life, it’s tough to imagine him walking away from the fight game so soon.

On top of that, we have these words from McGregor’s longtime coach, John Kavanagh, reassuring us that the biggest star in MMA isn’t anywhere close to the finish line:

“Like any sport there’s a sell-by date,” Kavanagh told the Irish Mirror recently (via Daily Star). “But Conor is 28; he’s a baby in the sport. I look at Bernard Hopkins, who’s 50, winning world title fights, so Conor isn’t going anywhere soon.”

There are a couple of factors that give me pause, though, and I’ll tell you what they are.

For starters, even if McGregor doesn’t intend to walk away after this Mayweather fight, I wonder if making those “tens of millions” of dollars you spoke about might have the effect of letting the genie out of the bottle for him.

Let’s say you’re Conor McGregor and you make $30 million to lose a lopsided decision to Floyd Mayweather in a boxing match. How interested are you really going to be in returning to the UFC afterward to make less than half that to fight Diaz or Tony Ferguson or Khabib Nurmagomedov? My guess is, not very.

One thing we know about McGregor: He’s continually upped the ante on the UFC in every contract renegotiation. Last we heard, he was asking for an ownership stake in the company before he would return. I seriously doubt that scoring the Mayweather fight would make his demands any more reasonable.

I don’t know. I just have a hard time seeing McGregor and the UFC getting back on the same page after he’s tasted the sweet riches of this superfight. 

Second, McGregor obviously isn’t your average fighter. He’s certainly not Hopkins, nor do I think he’s likely to turn out like Anderson Silva, trudging along into his mid-40s as his skill set decays and his place in the sport shifts from top dog to fodder for younger up-and-comers. 

The things that have really set him apart—aside from that thunderous left hand—are his brain and his mouth. He knows that, obviously, and he seems self-aware enough not to press on with his fighting career too long, thus endangering his future ability to enjoy all the neat stuff he’s collected into his golden years.

Then again, I just spent an entire one of these articles pontificating with our colleague Jonathan Snowden that nobody seems to know when to walk away from this sport, so who knows.

What do you think, Mike? If McGregor clocks big bucks to fight Mayweather, will the UFC ever get him back into its sway? Or might losing to the boxer actually make McGregor’s future demands more reasonable? 

Chiappetta: Let’s take your questions one at a time.

Certainly he will return to the Octagon. I have almost zero doubt of that. The fact is, after fighting Mayweather, nothing is going to pay him the amount of money that he can make by stepping into the cage again.

As long as he puts in a credible performance and entertains the masses, his star should stay on the rise, and the wider sports world should offer him credit for having the courage to step into a master’s world as a rookie.

Assuming that a loss doesn’t diminish his drawing power in any meaningful way, he’ll still have multimillion dollar checks coming his way in the UFC, and even if the per-fight money is less than what he will make for taking on Mayweather, won’t those huge paydays still draw him in? I think they will. Everyone realizes that this Mayweather purse is the payday of a lifetime, so it stands to reason that the ones afterward won’t be quite as large. That doesn’t mean they’re not still enriching.

Now let’s discuss your second question. The way I see it, McGregor’s demands have always been “reasonable.”

All he’s demanded is a bigger share of the pie he’s helped create. When we see UFC pay-per-views bottoming out at 150,000 to 200,000 buys and his headline act draws close to 10 times those numbers, it’s no longer an assumption that he’s responsible. It’s a fact. 

It was a pretty open secret that there has been some tension between the McGregor camp and the UFC brass over the sharing of the revenue he generates, and that’s not likely to change after a fight with Mayweather. In fact, it’s likely to increase.

Which leads me to my crazy and completely unfounded question of the day:

Could the UFC secretly want him to lose here?

As I stated, a loss to Mayweather isn’t likely to damage McGregor’s star power much, but it is bound to alter it somehow. 

White has spent enough time around the boxing world to know that McGregor’s almost certain to lose, so maybe they are thinking that aside from taking a handsome cut in exchange for lending McGregor out from the promotion, they may weaken his bargaining power a bit and take back some control at the negotiating table? 

I acknowledge that this is a tinfoil-hat kind of theory, and most likely, the WME-IMG brass is happy to see its biggest star grow his Q-Rating even higher, but…it wouldn’t exactly be a first to see the UFC undercut one of its stars, now would it? 

Chad, look into your crystal ball. First, do you agree that McGregor will find his way back to the UFC cage, and if so, how does a Mayweather experience change his UFC career arc going forward?

Chad: Yeah, I suppose if I had to bet the house on it one way or the other, I’d wager McGregor eventually returns to the UFC. But I’m not quite as certain about it as you are.

I agree that McGregor seems unlikely to turn down future earnings and that he’s given every impression of being a fighter’s fighter up to this point. Perhaps the most likely outcome here is that he goes on being that guy well into his 30s and even his 40s. You know, just like everybody else.

But I also think it’s fair to say that in many ways McGregor has broken out of the mold of the typical MMA fighter. Since his arrival on the big stage in 2013, he’s been smarter, shrewder and flat better at most aspects of the fight game than almost anyone in recent memory.

So, if you told me that McGregor is at work on a larger, more cunning plan—to get his money and get out with his health intact—I wouldn’t be surprised to hear that, either.

The extra and perhaps most tenuous layer to this onion is the notion that the UFC and McGregor can go on partnering long term, when it’s clear the two sides are working vehemently at cross-purposes.

Like you, I think the UFC understands the importance of protecting its investment in its biggest—and, at the moment, perhaps only—legitimate pay-per-view star. Also like you, however, it’s easy for me to imagine that UFC brass might not hate the notion of Mayweather taking McGregor’s political clout down a peg with a solid beating in the boxing ring.

Still, I doubt McGregor sees it that way. I don’t know how many ultramarketable matchups the UFC can serve up for him moving forward. I also doubt McGregor will settle for anything besides a larger and larger slice of the pie.

You and I agree that’s “reasonable,” but I’m not sure the fight company agrees.

Chances are, they figure it all out. But I’m still holding onto a slice of cynicism that says this relationship can’t go on as is forever. Somebody’s going to have to give a little, and so far I’m just not sure who that is going to be.   

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