Every journey starts with “What if…?”

Let me take you back to July of 1993, when I stepped in a ring in Toluca, Mexico with Julio Cesar Chavez.

He was the junior welterweight champion of the world at the time with a record of 87 wins, 0 losses and 75 knockouts.

I got in the ring to write a story about the experience for GQ Magazine. Fortunately, I am still alive to tell it.

For those who haven’t heard that story, I recorded it yesterday, and I’m sending it out to my e-mail community. You can listen to it here.

And if you want to know what that crazy adventure has in common with this weekend’s fight between Floyd Mayweather Jr. and Conor McGregor, read on . . .

Many insiders believe that Conor McGregor is not going to be able to lay a glove on Floyd Mayweather when the two step inside a boxing ring this Saturday.

I believe he will.

In fact, I think that no matter what the outcome is, Conor has already won. Why? Because he uses questions to change his life. Or maybe, it’s that Conor continually turns the same evergreen question on himself.

It seems to me that Conor is constantly wondering: What is possible? And he’s always coming up with a more outrageous reply, which forces him to climb to more incredulous heights.

August 26th is about as crazy at it gets. McGregor will take part in what will probably be the richest boxing match of all time. He’ll be facing the greatest boxer of a generation. And he will do so without ever having had a single professional boxing match.

Yes, he’s a mixed martial arts champion. Yes, he knows how to fight. But he will not be able to kick or elbow or choke out Floyd. He will be competing by Floyd’s rules.

Nobody has ever played the rules of boxing better than Floyd. What I’m talking about goes far beyond the fact that Floyd has won all 49 of his fights over the last two decades. And it goes way beyond the fact that Floyd is a defensive genius who hardly ever gets hit. Floyd has figured out a way to promote his own fights so that he controls the fighters’ purses and the event. In and out of the ring, Floyd makes the rules. You may not like his Money persona, but there can be no denying that he and his management team have disrupted boxing as a business.

Mayweather’s mastery is such that large audiences around the world have paid him more than $100 million in a night just to see if somebody can get close enough to him to land meaningful punches.

The fact that McGregor has no history in a boxing ring is exactly what will make people pay a record gate on Saturday. Can Conor, coming from an angle that Floyd has never seen, find a way?

I see no downside for Conor. That’s why I think he’s already won.

He says the fight will quadruple his net worth. Even if he gets knocked cold, so what? We’ll all say: How could someone with absolutely no experience expect any other outcome against one of the greatest of all time? And if Floyd dances untouched for 12 rounds and wins an easy decision, then Conor may take less of a beating than he would’ve if he’d defended his UFC title for much less money.

The gloves that Conor’s opponents in the UFC would be wearing weigh only four ounces. That’s not too far off from getting hit with a bare fist. The gloves that Floyd and Conor are going to wear in Las Vegas on Saturday will weigh eight ounces. Conor will be getting hit with gloves that have twice the protective padding than the gloves that usually strike him.

On top of that, Floyd has brittle hands, and is not known for having much power at or above 147 pounds. On top of that, after Conor weighs in at 154 pounds and rehydrates, he may be somewhere between 10 and 20 pounds heavier than Floyd, who fights around 147, when the two step into the ring.

Conor could have continued to defend his title in the UFC. But that is an obligation. There is no What if? in that.

This spectacle has so much more upside for him. And as slim as his chances are of winning, he does have some advantages. He’s almost two inches taller than Mayweather. The reach of his arms is two inches longer than Mayweather’s. He’s in his prime at 29 years old. Mayweather is past his at age 40. And Conor will be firing his wrecking ball of a left hand at a man who’s been retired and hasn’t fought in almost two years.

We don’t know how much Floyd’s reflexes have slowed, or if he’ll be vulnerable to the punch that never touched him in the past.

We don’t know if Conor can get inside and clinch with Floyd, where he’ll be able to smother him like no other boxer has ever been able to do.

And if he is able to do so, we don’t know if he’ll be able to figure out a way to land effectively off of it.

These, to me, are the question marks in this fight.

So here’s what I’m predicting. That Conor puts on a much better performance than anyone anticipates early on. But that he is completely bewildered by Floyd’s speed and straight right hand. It will come at him again and again, stinging virtually the same spot on Conor’s face over and over. Conor’s face will begin to swell, and soon he will get cut over the left eye. The blood will flow into his eye and the fight will be stopped on him.

Everybody will be in a huff over the way it ended because Conor was performing gallantly. And guess what happens next? The rematch!

And an additional hundred-million-dollar payday!

All of this because Conor wondered: What if . . . ?

Trust me on one point. Conor will land a punch.

I get that feeling every time I look up from my desk and see a miraculous photo. A photo of me in boxing trunks hitting world champion Julio Cesar Chavez when he was 87–0 with 75 knockouts.

I had no business being in the ring with Julio. I am not a boxer. I am a writer, and now a speaker. It was absurd to find myself in a situation where I was even sparring with one of the greatest fighters to ever live. But it happened only because I asked myself a big “What if . . . ”

If Julio had wanted to, he could’ve doubled me over and knocked me through the ropes in seconds. He went along with my What if . . .? because it made for a good magazine story and he has a good heart.

It’s a long story. And it can be hard to explain when one of your young children looks at that photo and asks: “Did you win, dad?”

I could only try to explain the difference between someone who’s the best in the world at what he does and someone who had a dream and trained for it for several months. No, I tell my kids. I could never have beaten Julio Cesar Chavez.

But deep inside I know I did win. I know that because this photo is on the wall. I won simply because I asked myself: What if . . . ?

See you next week,

Cal

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