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McGregor vs Mayweather: The Greatest Fight to Never Happen

Two once in a lifetime talent’s, two superstar fighters, two intelligent businessmen and one mega fight that we’ll never get the chance to see. As a pretty avid UFC fan and also someone who can appreciate what Floyd Mayweather has done in his career, I truly believe Conor McGregor and Floyd Mayweather will never go toe to toe inside of a ring.

Okay, so for the basic level fan of these sports this is what you need to know. Unless you’ve been living under a rock for the last year and a half you MUST know who Conor McGregor is. He has the mouth that will remind you of Muhammad Ali or for the younger generation maybe you could compare him to Reggie Miller.

But trust me when I say no one can
honestly compare to Conor’s trash talking and skills on the mic. His flashy and loud personality is all over social media. His Instagram account (@thenotoriousmma) is filled with ridiculously expensive cars, clothes, and other exotic activities we can only dream of. He is also the reigning, defending two division champion in the UFC. Holding belts in the Featherweight and Lightweight division, a first by any fighter ever in the UFC.

Floyd “Money” Mayweather on the other hand has dominated boxing since he first entered the sport professionally back in 1996. Now retired, Mayweather has also started his own boxing promotion. In 2007 he started his own firm after defecting from Bob Arum’s Top Rank promotion. His last fight, against Andre Berto was in 2015 ended in a victory for Mayweather and improved his record to 49-0 and brought his career earnings up to a substantial $700 million. So to say that Mayweather has been a huge draw for over nearly 20 years would be a backhanded compliment.

Now that you have a sense of what these two guys are about, here is why there isn’t a chance they step into the ring to square off. If you remember back to 2009 it was reported that Manny Pacquiao and Floyd Mayweather had come to a deal to get a contract struck up and signed. The two biggest names in boxing in roughly the past two decades to finally step into the ring…. but they didn’t. After some back and forth from both sides it seemed that Mayweather’s terms were too crazy and demanding for Pacquiao’s liking. Mayweather had demanded what he wanted the fight to be called “Mayweather vs Pacquiao”, he wanted Pacquiao to enter the arena first, be announced first and even called for Olympic drug style testing. Mind you, this was just the first round of negotiations. This back and forth would happen for the next six years.

Eventually the two sides were able to come to terms on a fight contract. In January of 2015 (remember, the talks started in 2009), Pacquiao agreed to terms of for a fight to happen in May of that year and it was all up to Floyd to sign the dotted line and the deal would be done. A couple of days later the two finally met each other face to face for the first time during an NBA game between the Miami Heat and Milwaukee Bucks in Miami and Mayweather signed the contract in February for a bout to happen in May.

The reason I bring this up is because Floyd Mayweather is a business man and is only going to make business deals that workout in his favor. Mayweather went on to win that mega fight against Pacquiao, with ease. Mayweather who is called one of the best defensive boxers in history counter punched his way to a unanimous decision victory. After years of negotiating and making sure he was going to get paid what he wanted and his needs were met, Mayweather agreed to this fight.


Now I want to you think about this, it took 6 years of negotiating for two boxers to come to an agreement on a deal and for the fighters to get into the ring. Now when it comes to Conor McGregor vs Floyd Mayweather, these are two different promotions trying to each get their fighter in the same ring, that is going to take a lot more negotiating.


Small steps have been made though to legitimately get the ball rolling if this mega fight were to happen. Real offers have been made by both sides in forms of cash and also in regards to Pay Per View splits. Floyd Mayweather’s team has offered Conor McGregor around $10-$20 million and a share of the Pay Per View buys. Whereas UFC President Dana White has counteroffered offering both fighters $25 million and shares of the Pay Per View. Floyd Mayweather shrugged that offer off faster than a Pacquiao punch as he’s looking for upwards to $100 million for this bout. Also another tidbit to mention, Conor McGregor has gone out of his way to get a boxing license in the state of California.

So is it out of this world to think this fight will happen, no. But it’s going to take a lot of patience for these two sides to get a deal done. There are a lot of ego’s in this conversation on both sides of the table. Floyd Mayweather is going to have to allow Conor and the UFC to get paid what they want since they are the ones coming onto the boxing turf. Dana White and Conor are also going to have to try and get along with Mayweather and his promotion team to strike a deal. These businessmen all could work out a deal that could make everyone a lot of money but it could take a very long time and I’m not too sure all these egos; Mayweather, McGregor, Dana White, and the UFC can be checked at the door.

About Matt Jackson

- News Technical Director in Albany, NY - Former NYR Reporter for Stan Fischler - Washed up hockey player

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