The Money Fight

Floyd Mayweather x Conor McGregor

Putting the world of combat sports on hold

I feel dirty giving this fight any more attention but if there was ever a boxing match that's forced its way on my radar, this is it. 

Boxing was a sport I used to fawn over when I was younger, until I found kickboxing. My affair with kickboxing lasted until I found MMA. Once I started following MMA, I rarely looked back. I love combat sports and, to me, when a fighter has more tools at their disposal, we get a more compelling matchup. Less restrictions create more opportunities to succeed and more opportunities to fail – higher risk and higher reward. I like to see a fighter’s strengths and weaknesses play out on a larger scale as the match transitions from one proficiency to another. When rules become more stringent, like in boxing, specific skills, like movement or punching, develop at higher levels because there is less to worry about. Not only higher levels, but different levels. Boxing in MMA is nothing like actual boxing. In MMA, if a technique works, it’s a good technique. In boxing, bad technique will get you knocked flat on your back. When only one element of fighting is at play, it turns into a much deeper art form. You’re expected to excel in one area as opposed to being moderate in multiple aspects. To me, that’s not the best way to emulate a true fight, but that doesn’t mean it shouldn’t be heavily respected.

When you zoom in on one area of expertise, gaps begin to magnify. The definitions of speed and power change. Defense is different. Offense is different. Everything is different. Professional kickboxers and boxers can get knocked unconscious in MMA because they can be misdirected with long list of unusual techniques. Forcing them to grapple and wrestle obviously creates a whole other series of problems – see former heavyweight boxing champion James Toney’s MMA fight against former UFC heavyweight champion Randy Couture from 2010. Toney wasn’t even able to throw a punch. By no means could Randy step into a boxing ring with James Toney, not even on his best day, and survive. It’d be lights out, naturally. That’s the beauty of developing and showcasing a well-rounded skillset. That’s also why this match is going to be so difficult for Conor.

No MMA champion has ever made the transition to professional boxing – especially not at this level. For Conor McGregor to walk right into the ring against arguably the greatest boxer of all time is a feat beyond comparison. From a marketing and promotional standpoint, it’s brilliant. Boxing is notoriously shrouded in shady dealings and to weasel your way to the top of the heap, while being backed by the UFC, seemed impossible. This situation also falls on McGregor’s long list of predictions he’s made about his own career. Nobody has ever, EVER, co-promoted with the UFC and now not only are they co-promoting with Showtime and TMT but they’re also promoting with McGregor Sports and Entertainment. That’s right, Conor has got his hand in every piece of the pie. What also helps smooth the process over is that there’s hundreds of millions of dollars to be made. If there’s anyone who can make the transition work, it’s Conor McGregor. The brash Irishman is the biggest PPV draw in UFC history and he’s also the only person to simultaneously hold belts in two weight classes. He deserves this concession. Good for him, too, because even with a loss this will be his biggest payday of all time. The UFC, and MMA in general, notoriously underpays its fighters. The big money lies in professional boxing, but only at the highest level. It’s no coincidence that this is exactly where we find ourselves.

You can’t compete in combat sports forever and McGregor is acutely aware of this. It was only a little over a year ago that he pseudo-retired on Twitter, saying he was done and thanking us for all the “cheese.” I also can’t forget him repeating, multiple times, his mantra: “Get in. Get rich. Get out.” To be honest, that’s the only valid mindset to have in these sports. There’s no point in turning your brain into mush for $10,000 at a time. You need to be loud and marketable and have the skills to back it up. This is prize fighting, after all. Another man who is very aware of this is Floyd Mayweather. Despite having his first professional fight in 1996, Mayweather’s bold personality and defensively-minded style have kept eyes on him and fists away from his face. The man has taken very little damage enroute to amassing a stunning 49-0 record in professional boxing. Sure, you can say he’s cherry picked his opponents and made fights boring, but that hasn’t stopped people from tuning in. To have never been dropped, nevermind finished, in your entire career is inimitable. We may never see it again. In MMA, you’re guaranteed to get hit or choked or slammed or kicked because there are an uncountable amount of offensive options. In boxing, if you’ve mastered the science, you can be untouchable. That’s what Mayweather has proved and accomplished.

On a personal level, Floyd Mayweather seems like a deplorable person. The multiple charges of domestic abuse on top of the other horror stories you hear about the guy make him impossible to root for. His boxing, however, is bulletproof. In fights against Mayweather, opponents statistically threw fewer punches and landed fewer punches than they did in any other fights of their careers. Consistently. Floyd is more than hard to hit. His speed, timing, and counterpunching make him a defensive genius. He knows exactly when and where to punch and where to move. He usually lands at least 40% of his shots and while he’s not renowned for his power, he doesn’t have to be. His pacing keeps him fresh and nobody makes 12 rounds look easier. It’s aggravating to root against and hard to appreciate if you’re not across the ring from him. Either way, his competence in the sport undeniable. The only factors going against him, as far as the fans are concerned, are his age and his inactivity, as Mayweather technically retired just about two years ago. Those are simply variables to this fight, as all evidence points in the other direction. To briefly address the late glove size change from ten ounces down to eight ounces – whatever. He’s fought in eight-ounce gloves many times before, including in the Pacquiao fight. Neither McGregor nor Mayweather heavily utilize a traditional boxing guard and instead opt for head movement and footwork. When it comes to close quarters, Mayweather tends to clinch instead of cover up. Chalk it up to more pre-fight hype.

We’ve never seen Conor McGregor in a boxing ring, but even as a fan I can admit that there’s no way in hell he can develop the necessary skills to take on a primed Floyd Mayweather on his own turf. No way. McGregor’s movement is unparalleled in MMA but, again, that’s where the differences between the sports shine. McGregor likes to hop around and work the body, comfortable as he methodically goes for the kill, because there aren’t gigantic gloves or foul-protectors to stifle his shots. He also has some trouble moving backwards while defending, which is why he’s such an offensive-minded fighter. It’s almost exactly opposite of Floyd. McGregor’s “one-punch” power has also been oversold in this fight. He’s only had one clean KO in the UFC, against Aldo, and that’s because Aldo essentially ran towards him as soon as the bell rang. Don’t get me wrong, McGregor clearly has heavy hands, but he uses his bag of tricks to set those shots up. His opponents are tired and confused by the time the finishing barrage lands. Precision and timing are his biggest attributes. Without kicks at his disposal, he will probably rely on his counter punching. I fully expect to see McGregor trash talk in the ring and do everything he can to frustrate Floyd into being the aggressor.

The key to victory for Conor Mcgregor, in my mind, is not to try to box Floyd. Instead, he’s going to have to skirt the traditional style and display unorthodox movement to take Mayweather out of a natural rhythm. If Conor can keep him confused during the opening rounds, he’ll have a chance to muzzle Mayweather’s timing and keep him guessing. Since Mayweather isn’t known for his punching power, there’s little risk to trying something new. Worst case scenario, McGregor gets peppered with counters and jabs for the entirety of the 36 minutes. Best case scenario, he shocks the world. After all the tall tales told by Pauli Malignaggi and the few seconds of training footage we’ve seen, I don’t know what to expect. It’s obvious Conor can box, but I don’t think he can box on a level anywhere near Floyd Mayweather. He’ll have a minor height and reach advantage, but his charisma and “flowy” movement are the X factors. The fact that Mayweather has never been dropped in his career speaks volumes. I’d love to see McGregor be the first man to get it done. I’d especially love to see Conor win. Not only because I’m an MMA fan, but because of the chaos that would follow. Both men are already legends in their respective sports, but for McGregor to come out ahead and still have a career left … it’d be unbelievable.

I don’t know what to expect and you shouldn’t pretend to know either. The safest bet is always that the boxer is going to win a boxing match. I’d love to go out on a limb and predict a McGregor victory, but that’d just be a lucky guess. There aren’t enough technical details available to make a bold prediction without it being rooted in hype. Instead, just enjoy the fight. These are two very different sports and it should be admirable that one of MMA’s best is willing to step up to the challenge. It doesn’t mean that boxing is better than MMA or vice versa. That’s subjective. It simply means that these two are willing to test each other out for a ridiculous amount of money. Who wouldn’t? This isn’t a circus, despite the critics. Both men are absolute professionals and I guarantee both of them are going in there to get their hand raised. A sideshow would be if I tried to fight either of them. That said, if anyone wants to hand me a couple million to get that done, please give me a call.


Ian and Evan are doing fantastic things over at Thanks Dad Podcast and were nice enough to invite me on to discuss the fight, among other things. If you would rather hear my drunken ramblings than read my sobering thoughts, make sure to listen to the episode. I did my best not to come off as a complete idiot.