This hopeful statement is characteristic of how many of McGregor’s fans see him and his chances. “I believe in my gut.” I’m not dismissing the value of intuition, even as it applies to boxing matches. I’ll suggest, though, that it probably applies more reasonably to a fight like Marvin Hagler vs. Thomas Hearns than to one between an elite, undefeated boxer with genius-level matchmaking skills and a debuting opponent.

Still, I have a feeling we’re going to see a lot of “my gut says he’ll win” bets, and those will continue to bring the odds down.

They’re Printing Free Money Out There

It doesn’t happen often, but there will occasionally be a fight whose winner will be obvious to anyone who knows boxing, but with odds that won’t reflect the ironclad certainty of the bet. Floyd Mayweather himself was involved in one of those fights when, as a betting lock, he took on Manny Pacquiao in 2015.

In a fight that Mayweather delayed and delayed until he was satisfied that the last vestige of doubt as to its outcome had been removed, the betting public still gave Manny Pacquiao a live underdog’s chance of winning, bringing him in at under 2-1.

Mayweather’s lead-pipe cinches over Pacquiao and now McGregor are only the most recent in a more than century-long procession of big fight flim-flams that have separated the credulous from their cash while allowing anyone with a smattering of clear-eyed analytical insight to pocket a bundle of money.

Insane misperceptions that impact the betting line almost always center on either the sentimentalization of an icon or an intense identification with a fighter based on nationalistic, cultural, or racial grounds. When both factors come into play simultaneously, fortunes are there to be had for the taking.

Here are some noteworthy fights where the odds were way out of proportion to what they should have been. Anyone with a rudimentary understanding of boxing would have known how to bet them.

Jack Johnson vs. James J. Jeffries

Odds: 2 ½-1 Jeffries

The Jack Johnson vs, James J. Jeffries fight (which took place in Reno, Nevada 107 years ago to the day that I write this) is probably the best point of departure (after the bare-knuckle era) for looking at free money betting opportunities.

At the time they fought, Johnson was in his prime—to that point in boxing history, the best heavyweight who’d ever lived—and Jeffries had been out of the ring for nearly six years, having ballooned up almost 80 pounds to nearly 300 during his recess.

Jeffries had been a formidable champion, a fighter of ungodly physical strength and an indefatigable constitution. Those days were gone for good. More significantly, Jeffries knew he couldn’t bring them back. He was also discomfited by the social pressure thrust on him by people like the writer Jack London. (“One thing now remains. Jim Jeffries must emerge from his alfalfa farm and remove the golden smile from Jack Johnson’s face. Jeffries, it’s up to you! Jeffries, it’s up to you! The White Man must be rescued!”)

Jeffries didn’t want to rescue The White Man. He really didn’t want to emerge from his alfalfa farm. He just wanted the $100,000 payday that would keep it operating. He broke down in his dressing room, knowing what he was about to endure.

Jeffries’s beating was probably even worse than he imagined it would be, made more intolerable by Johnson’s glee at being able to keep up a running conversation with him—and with former champion James J. Corbett at ringside—while beating the shit out of him for 15 rounds, stopping only when the old fighter’s corner stepped in to spare him the indignity of being counted out in a fight against a black man.

Afterwards, Jeffries said, “I could never have whipped Johnson at my best. I couldn’t have hit him. No, I couldn’t have reached him in a thousand years.”

Rocky Marciano vs. Joe Louis

Odds: even money

There’s no arguing that Rocky Marciano was and remains one of boxing’s most admired, respected and, in some ways, fetishized heavyweight champions. He is the only one of them who retired undefeated. He brought to the title a Spartan dedication to training that connected him not only to a generation of Italian workers who’d recently emigrated, but to blue collar fans of every ethnic background.

But Joe Louis was Joe Louis. Until the ascendance of Muhammad Ali, no boxer held anywhere near the sway over the American public that Louis did. And Louis was a far less polarizing figure than Ali. It’s not an understatement to say that people worshipped Joe Louis.

When Louis’s money problems brought him back to boxing in 1950, he returned as a vastly diminished fighter. He was beaten decisively in attempting to regain the heavyweight title from Ezzard Charles, but spent the following year building an eight-fight win streak. At this stage his power had deserted him; only three of those wins were by knockout.

Photo credit: AP
Photo credit: AP

The wins managed to get him another title shot, this time against Marciano. But he was an old 37—slow of hand, foot, and reflexes, dispirited, and entirely physically burned out. Everyone in boxing knew he had no chance against Rocky.

The public couldn’t accept that Joe was through, and their betting money matched the smart money. Louis started the fight adequately, but he was progressively worn down by Marciano’s nonstop assault to the body. Round by round Louis’s hands came down, giving the tireless Rocky the openings he needed to finish things. In the 8th, Louis was dropped with a left hook to the head. He beat the count, but was in terrible distress. He attempted to tie up, and, when that failed, tried to just lay his weight on Marciano. Rocky having none of it, knocked Louis through the ropes with a hook to the head, followed by two thumping rights, all disquietingly hard punches.

The image of Joe Louis down and helplessly entangled in the ropes, half in and half out of the ring, broke hearts the world over. In his dressing room, despite his win, the champion could not stop crying.

Sonny Liston vs. Floyd Patterson

Odds: 7 ½-5 Liston

I’ve got a story that illustrates how hopeless Floyd Patterson’s chances were against Sonny Liston in their first fight, and just how risk-free betting on Liston was.

Patterson and I were business partners for quite a number of years in the 1990s, and spent many late nights at his home in New Paltz, New York, drinking pot after pot of coffee and talking. We had business to discuss that centered on the boxers I managed and he trained. But, as dark became dawn, the talk would drift. Floyd was the kind of guy given to reflection and reminiscence, and so was I to a degree. I could be reasonably sure that eventually Patterson would begin to talk about his time in the ring with Liston and Ali. Sometimes I’d steer the conversation in that direction.

“Who was the hardest puncher you ever faced, Floyd?”

“Ingemar Johansson. “

I knew that wasn’t true, but I also knew that Floyd was honest to a fault.

“Ingemar Johansson? How is that possible? You fought Sonny Liston.”

Patterson smiled his self-deprecating smile.

“Oh yes, but when I fought Ingemar, I thought I was going to win.”

You know a fighter’s chances of winning aren’t too good when even he is sure he’s going to lose.

Photo credit: AP
Photo credit: AP

The Liston vs. Patterson fights were racially charged, as were a number of the free money fights under review here, with Patterson a stand-in for the White Hope. Suckers bet with their hearts, blind to the situation on the ground. Boxing people knew better. It was crazy to bet against Sonny Liston unless someone on the inside clued you in when it was the right time to do so.

Larry Holmes vs. Muhammad Ali

Odds: 6-5 pick ‘em

By the time Muhammad Ali fought Larry Holmes at Caesar’s Palace in 1980, he no longer was a great fighter. The fact is that, at 38, he wasn’t a fighter at all. He was simply an unwell man standing on the edge of the cliff that, pushed this last time by a disgusted and reluctant Holmes, he would slowly roll down for the rest of his life.

For the event, Ali trotted out some lightweight trickery. He lost weight. He grew a mustache and dyed his hair black. Realizing that the mustache made him look older, he shaved it off. A performer of past miracles and an idol adored by the public in unheard-of ways, he promised the world that he would not disappoint; he was back, bigger and better than ever, ready to do the undoable one more time. The world believed him, and bets were made accordingly.

Holmes, distaste for the task evident in his pained and angry expression, went about the thankless job of knocking Muhammad Ali out without killing him. It wasn’t an easy thing to do. But Holmes was one of boxing’s greatest craftsmen and—to his eternal credit—he found a way to navigate the weird and treacherous dream-ring that night, somehow managing to get the job done in a way that was as humane as could be hoped for under the circumstances.

Larry Holmes vs. Gerry Cooney

Odds: 6-5 Cooney

I like to fantasize that in his two biggest fights Larry Holmes was somehow able to get bets down on himself large enough to pick up whatever he didn’t already own of Easton, Penn. Disrespected when he fought Muhammad Ali, Holmes had to endure a series of indignities nearly two years later when he was again not seen as a favorite in a fight where he should have been 3 or 4-1. He had to accept purse parity (albeit by far his best payday) against Gerry Cooney, an untried opponent whose career had been steered masterfully by two moneyed boxing outsiders, who combined risk avoidance, white pride, Irish pride, Long Island pride, and any pride other than black pride with an endless promulgation of the power of their charge’s left hook to build a media sensation.

Mike Jones, one of the moneyed guys, didn’t have much of a head for the business. The other, Dennis Rappaport, did. I know Rappaport, and there was a time when he and I talked on the phone very often, and in person occasionally.

Rappaport had a reputation for being difficult and eccentric. He was neither. Nor was he in any way racist. When I met Dennis, he was managing Melvin Foster. He had briefly managed Mitch Green before I did, and still had a cordial relationship with him. Neither Foster nor Green would have held any interest for a racist manager. Without having cultural empathy for them, it would be impossible to form a relationship, business or otherwise. But, like anyone who works outside the insular boxing establishment, Rappaport was regarded with mistrust, dislike, and envy by those within it.

Rappaport wasn’t a boxing guy, but he was smart enough to ask millions of questions to the people he knew were. He listened, he learned, he thought out loud when he talked to you, he spent his own money when he had to, and he promoted the shit out of his fighters. Gerry Cooney was one of the best-managed fighters in boxing history. He earned $18 million—enormous money at the time—for the three fights he lost.

Photo credit: AP
Photo credit: AP

25-0 when he went up against Holmes, Gentleman Gerry had waded first through beginners, then journeymen deemed safe, and culminated his trip to the top with three consecutive early kayo wins against former headliners (Jimmy Young, Ken Norton, and Ron Lyle were quality opponents who’d done well against Muhammad Ali) who were long in the tooth. These eye-popping knockouts looked a lot better than they actually were, but they got the job done. Cooney came into his title shot as the most talked-about challenger in recent years.

Naturally insecure, unsettled by fear, Cooney fought way beyond himself the night he met Holmes. He did things that those who promoted, managed, and trained him didn’t think he was capable of. He fought a desperate, dirty, ugly fight dominated on his part by mostly uncalled low blows. Against any other heavyweight in the division, it would have been enough to get the win. Against Larry Holmes, at his focused, calculated, and quietly seething best, it was not nearly enough. Holmes, concerned that he wouldn’t get a fair shake from the judges (he was right, as it turned out), knew not to leave things in their hands.

If Cooney was at his career best, Holmes was at least close to his. He had an answer for everything thrown at him, and over 13 draining rounds, he clinically beat Cooney up, bringing him further and further from land, reminding him constantly that he would eventually drown in a horrible way.

Cooney’s trainer Victor Valle, a wonderful and gentle man from rural Puerto Rico (he grew up near where I own a farm), could no longer stomach the beating his charge was taking, and stepped into the ring as the 13th round was coming to an end. He threw his arms protectively around Cooney, whom he regarded as a son, and the fight was stopped. Valle was criticized for his move, but it was the right thing to do. I hate to think of what Holmes would have done to Cooney in the final two rounds to ensure that the fight didn’t go to the judges’ scorecard.

Floyd Mayweather vs. Manny Pacquiao

Odds: 2-1 Mayweather

Once some dust settles on recent boxing history, Manny Pacquiao will be viewed as having been a better fighter than Floyd Mayweather, Jr.. A lot of elements factor into the assessing of boxing greatness, and who could beat (or, in this case, did beat) whom is just one of them. Longevity, level of opposition, and the willingness to take risk are also primary components. Pacquiao, who began his boxing career as an undernourished boy in his native Philippines, never ducked a challenge as he moved up in weight, tearing through what at each stage appeared to be a bridge too far. Until he hit his personal ceiling, an obstacle determined mostly by age and lack of size, he was a dynamo, an exhilarating thrashing machine that rendered opponents—even name opponents—suddenly inert and obsolete. Watching the prime Pacquiao in the midst of his joyous annihilations, one thought of dinosaurs being picked off by smaller, faster, smarter, and more mobile predators.

But, unlike Mayweather, Pacquiao was never perfect. There were always holes in his game, ready to be exploited by the few fighters savvy enough to spot and act on them. If anything, this element of recklessness and vulnerability made Pacquiao, if not a better fighter, a more beloved one. He would put whatever he had on the line for fight fans.

All this means that, even at his very best, Manny Pacquiao could never have beaten Mayweather. The boxing axiom “styles make fights” is almost invariably true, and Mayweather’s style was particularly poorly suited to Pacquiao.

The highest-grossing fight in history didn’t even wind up qualifying as an acceptable sparring session. Mayweather hit Pacquiao enough to keep him from getting fresh, taking round after boring round for a unanimous decision.

Floyd Mayweather, Jr. vs. Conor McGregor

Odds: started at 225-1, currently 4-1 Mayweather

Mayweather’s masterpiece. TBE. The Best Ever, hands down. Forget Tex Rickard and Don King as promoters, Doc Kearns or Ray Arcel as managers, Bruce Trampler or Harry Markson as matchmakers, or Abe Attell or Frankie Carbo as fight-fixing gamblers; as great as they all were and are, Mayweather’s August 26th score eclipses anything anyone has done in boxing outside of the ring. If he doesn’t make another hundred million betting on the fight (one way or another), he will still walk away with more than $60 million for facing the single most ill-equipped, unprepared opponent a championship-caliber fighter has ever found in the opposite corner. Every wiseguy who has ever engineered a Help Yourself money grab is shaking his head in stunned admiration. Floyd Mayweather, Jr. is the Sugar Ray Robinson of promoters, managers, and matchmakers.

White Males On Parade (If Not In The Octagon) 

In the United States, MMA is a young white man’s sport. It doesn’t too much matter where its practitioners are from; the zeitgeist remains white, male, and aggressive. A lot of the money is going to be spent wagering on Conor McGregor to beat Floyd Mayweather, Jr., and it will be inspired by white longing. While identification is often a main ingredient in impossible-odds betting, adding the MMA component brings in an increased element of transference, a sense of “That’s me in the ring with him.” The fighter doesn’t only represent the spectator; he is the spectator. “I’m the same size as Conor McGregor. I’ve studied martial arts, I can strike, I know some Brazilian jiu-jitsu, I do cardio. Mayweather’s an old man, and I’m 23. I kicked Jeffy Gilford’s ass in middle school, and he was a little, mouthy black dude.”

The size thing matters. In racially-charged hysteria bets like the ones that allowed James J. Jeffries and Gerry Cooney (and even, oddly enough, Floyd Patterson) to be favored over their obviously superior opponents, the bettors weren’t picturing themselves up in the ring. They knew that, if they tried, Jack Johnson or Larry Holmes or Sonny Liston would beat them up and laugh at them while they did it. There’s an element of heroic deputization in getting a big white guy to do your dirty work.

Contempt And Legacy

In one profound way (if the term “profound” can be applied to anything about this operation) Floyd Mayweather, Jr.’s legacy, such as it is, can only take a massive hit from the fight; Conor McGregor’s, short of fainting just before the opening bell or being knocked cold by the first punch he’s hit with, can only be enhanced.

This fight is a Hall of Fame MLB pitcher doing a public relations stunt by throwing to a star Little Leaguer. If he drills the kid, he looks like a monster; if he tosses him a soft underhand pitch, he looks like a condescending dick playing with a child.

In this sense, Mayweather, with all of his options once the bell rings, is actually stuck in a box of his own making, since most of those options require him to let McGregor look better than he actually is. Even torturing Conor in a cat-and-mouse game is going to bring up questions as to why Floyd couldn’t get the fraud out of there sooner.

If you’ve worked creatively over 20 years to successfully convince people that you’re the greatest fighter who ever lived, you really have to look like the greatest fighter who ever lived if you’re against a beginner. How do you do that? What does it look like?

The greatest fighter who ever lived isn’t a real person if that designation is bestowed during a boxing era where conditions don’t allow for a viable chance to prove it. If your weight-lifting set only has 300 pounds to put on the bar, the bar can’t hold enough weight for you to be the world’s strongest man. You can say you are, and, because you haven’t failed, your claim can’t be quantitatively refuted, but you better power those 300 pounds over your head as if they were feathers if you don’t want everyone watching to start laughing.

I Finally Bite The Bullet And Watch Conor McGregor

I take my colleagues who make cases for Conor McGregor’s legitimacy seriously, but still can’t come up with anything that McGregor can do that would give him a remote chance of being in this fight. He’s not even a serious Golden Gloves-level fighter. Paying him $20 million or more to box is no different from paying a pro wrestler to box. It’s no different from paying Bobby Fischer to box. Yet smart, informed combat sports people aren’t entirely laughing this debacle off.

Here’s what I see.

Sparring: McGregor walks directly into punches. He keeps his hands too low, and is forced to constantly make adjustments to block and throw punches. These adjustments are done too slowly, with no sense of anticipation as to either where the incoming punch will land or where his own punch should go. In coming forward, he often presents himself as a square target, and he doesn’t move his head. He loops slow punches from the outside, leaving himself entirely vulnerable to counter shots. His footwork is poor, alternating between a too wide stance that simultaneously makes him unable to punch and susceptible to being knocked off balance, and an overcompensating tendency to place his feet nearly together, a mistake that will produce the same sorry results as the overly wide stance. By pro boxing standards, he has no power at all. When moving around the ring, he often crosses one foot in front of the other, a recipe for being embarrassed by any boxer better than a novice pro with a losing record.

Grade: F

Boxing training: I’ve watched some of McGregor’s bag and drill work, and find it difficult to know whether he’s serious about some of what he does. There’s a highly performative element to much of what I saw. That’s not necessarily a bad thing; it clearly establishes McGregor’s general fitness, athleticism, and natural coordination. The question is whether the aspects of his training that are most impressive—yoga-like stretching and acts of balance, deft pivots, strenuous calisthenics—can be usefully applied when he’s in a boxing ring. He hits the bags and jumps rope about the same as everyone else who is serious about those things. His mitt work is pretty bad.

Grade: Incomplete

Out of the gym, on the mic, etc.: Here’s where Conor McGregor earns his share of the purse. Although Floyd Mayweather, Jr. is a veteran self-promoter whose work behind a microphone must, by virtue of what it’s earned him, be considered successful, he is not a gifted talker. He comes across as either querulous and petty or solicitous. He is a man without charm, a smaller-than-life figure. He was catapulted into superstardom on the backs of two opponents—Ricky Hatton and Oscar De La Hoya—who were the A sides of the promotions at the time they lost to Floyd. The minor accomplishment of beating them (Pacquiao, to compare, effortlessly annihilated both) served as the catalyst for Mayweather’s TBE mantra.

Conor McGregor, his costly custom (but too small) suits and designer eyewear serving to call attention to his gargoyle head with its jutting chin and outlandish red beard, draws the eye in a public venue in a way that Mayweather does not. He is at once both compactly efficient and ridiculously oafish—someone who boxing people would tell you was born to be knocked out were he to make the mistake of genuinely seeing himself as a prizefighter. He is graceful in a way, but also—again, by boxing standards—parceled out in his movements. They are too precise, too fussy, and too brittle when not engaged in fight-related activities. Even if his body is capable of doing things that great boxers’ bodies might not be able to, it doesn’t move with the ease that theirs do.

McGregor can talk. He falls short of being loquacious, but he has the prized Dublin gift of gab. On the mic, he has energy, humor, and a pugnaciousness that people will either be drawn to or put off by, responses that are equally bankable. Although much of what he says stays close to predetermined Poor Boy Makes Good narrative (“Like many folks in Ireland, my family didn’t have much. My parents struggled to pay the mortgage. They’ll be struggling no more.”), he listens closely to questions posed by interviewers and he can improvise. When asked by Conan O’Brian what he thought of José Aldo backing out of their fight by claiming a rib injury, McGregor deadpanned, “Really I cannot hold any grudge towards him, because I would not want to face me either.” He paused, then added, “He has been medically cleared to fight. Doctors have looked at him, examined him. He went and saw a gynecologist.”

From an impromptu interview when someone on the street thrust a mic in his face: “I’m the boxing guy. Watch me take over boxin’. Trust me on that. No one in this boxing game knows what’s comin’. Trust me on that. When I step into that ring, I’m gonna show the whole goddamn world. Trust me on that. Look me in the eyes! Twenty-eight years of age. Confident as a motherfucker … I’m gonna stop Floyd … the whole world is gonna eat their words.”

He’s got certain rhythms down pat. The “Trust me on that” riff is exquisitely timed, a preacher bringing the flock into his confidence. A con man is a confidence man. Back me, trust me; I won’t let you down.

Grade: A

The Shoe On The Other Foot, Or, A Lesson In Dumb Chauvinism

What happens when a great fighter moves out of his métier to try another great fighter? He gets beat up and embarrassed fast. While doing that, he drags all of his defenders down with him.

Count me as one of those defenders. Not knowing about MMA, I confidently picked James Toney to knock out Randy Couture with the first punch he landed. I was entirely sure that punch would land within 10 or 20 seconds.

James Toney had, at the time of that fight, been a professional boxer for 22 years, during which time he won world titles from middleweight to heavyweight, beat most of upper tier opponents in his weight divisions, ducked no one, attempted to bait anyone near the top of the pyramid to get into the ring with him, and never once came near getting knocked out. Toney is an all-time great—one of the half-dozen best boxers of his era. He’s a better fighter than Floyd Mayweather.

So I was one of the many boxing people who was turned into a yokel, staring slack-jawed at the TV screen as Couture, who looked middle-aged and moved with all of the urgency of an armchair athlete reaching for his TV’s remote control while taking Toney down, rained harmless punches on his head, all thrown as distractions to set up his submission move—an arm triangle—which he effortlessly applied, and caused Toney to tap out barely three minutes into the match, a suddenly beached whale whose long-established persona of menace had been instantly erased.

Apples and oranges; I had to admit that to myself. My ironclad belief that a boxer would knock out an MMA fighter in the time it took him to cross the ring was finished. I had to acknowledge that boxing and MMA were specialized sports, and anyone crossing over, not spending many years in training exclusively for the technical adjustments, and stuck confining themselves to the strictures of new rules, was going to get their head handed to them.

Trump, Trump, Trump And The Culture Of The Impossible

A sentence that Donovan Craig sent me when assessing Conor McGregor’s chances in the fight keeps coming back to me.

“Mayweather vs. McGregor is the boxing equivalent of the Trump presidency, a once seeming absurdity that was somehow talked into existence.”

Photo via @DonaldTrumpJr
Photo via @DonaldTrumpJr

Talking nonsense into existence is one thing. It might not be easy, but it’s far from impossible to do. But Donald Trump won, as Donovan mentions. Trump is at every level an inept clown—much less well-equipped to be a president than Conor McGregor is to be a successful boxer—and yet a credulous nation longed him into being. Maybe his opponent got jobbed out of the decision, but she’s not the one sitting in the White House.

I was as confident that Hillary Clinton would destroy Donald Trump as I am that Floyd Mayweather will destroy Conor McGregor.

And Finally, A Word To The Nevada State Athletic Commission

This is none of my concern, and how the idiots on the Commission board enrich themselves and bring revenue to the state is their business, but these dumb motherfuckers should never again have a voice in who is or isn’t allowed to box in Nevada. If Charles Manson applies for a license to fight Anthony Joshua at the MGM Grand in Vegas, they better not have the audacity to withhold it from him.

Charles Farrell has spent most of his professional life moving between music and boxing (with a few detours along the way). He has managed five world champion boxers and has 30 CDs listed under his name. His essay “Why I Fixed Fights” is included in the boxing anthology The Bittersweet Science: Fifteen Writers in the Gym, in the Corner, and at Ringside, edited by Carlo Rotella and Michael Ezra, and published by the University of Chicago Press. He is featured in the 2016 film Dirty Games, directed by Benjamin Best.