The Fight to Organize the 'Fight of the Century'

Saturday's face-off between Floyd Mayweather, Jr. and Manny Pacquiao is five years in the making, and the infighting behind the scenes highlights many of the issues facing modern boxing.

On Saturday night Manny Pacquiao and Floyd Mayweather Jr. will finally get into the ring together. They’re the two greatest welterweights of their generation, but it's nevertheless taken five years of negotiations to bring about what's being billed as the "fight of the century." At least for a weekend, the event has brought renewed interest to boxing: More than 2,000 people have applied for credentials, ticket prices are in the tens of thousands per seat, and the Las Vegas Convention and Visitors Authority estimates that between 94 and 98 percent of the city's 150,000 hotel rooms will be occupied this weekend as fans head to town to soak up the atmosphere.

The fight is a landmark event, and the two boxers will enjoy an outlandish payday for a night’s work, with Mayweather making an estimated $180 million and Pacquiao around $100 million. But the showdown also highlights many of the problems that have become engrained in the fabric of the sport: money-making taking precedence over exciting match-ups, combative divisions between promoters and networks, and the sometimes off-putting, carnivalesque nature of the sport's culture.

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The story of Saturday’s megafight begins with Manny Pacquiao. He grew up dirt-poor in the Philippines, dropped out of school in sixth grade, and sold cigarettes and donuts on the street. As he learned the boxing trade, his hand speed quickly earned him early success, though he had little technique. He eventually stowed away on a boat to Manila, where he worked construction jobs and started boxing professionally. He became a sensation on a Filipino boxing show called “Blow-by-Blow,” and his television-friendly style played well because he was preternaturally quick, took risks, and frequently knocked out his opponents.

In 2001, Pacquiao visited the United States and traveled on a Greyhound bus to the Wild Card Boxing Club in Hollywood, where he hooked up with the legendary trainer and ex-boxer Freddie Roach. Under Roach's tutelage, Pacquiao became a world champion in eight different weight divisions. In the Philippines, he’s a hero: a sitting Congressman who's known to inspire millions as he fights for—and gives money to—the poor. Pacquiao has fought the best boxers of his time, but there's a significant gap in his resume: He's never fought Mayweather.

Floyd Mayweather Jr. grew up in Grand Rapids, Michigan, surrounded by boxing: His father and uncle were exceptional fighters. Mayweather showed early prowess at the sport and would eventually go on to win an Olympic bronze medal. (His loss, in which the judges handed the victory to his outmatched opponent, is considered a travesty.) Then Mayweather turned pro and fought for the legendary promoter Bob Arum, who now works with Pacquiao. But Mayweather, who was then called “Pretty Boy,” felt hemmed in by Arum. He wanted to run his own show and create his own brand. So with the help of the Harvard-educated concert promoter Al Haymon, Mayweather bought himself out of his promotional contract and created the persona of “Money Mayweather," a big-talking, big-spending heel. The boxer, who hasn't lost in 19 years, is an exceptionally intelligent ring tactician who seems to out-think and out-box every opponent. His gamble to promote and brand himself has made him the highest-paid athlete in the world, according to Forbes.

Mayweather and Pacquiao started negotiating five years ago, and the dream matchup seemed close to fruition. But in 2009, Mayweather asked for random drug testing, which isn't normally the protocol in boxing. Pacquiao balked, claiming he was insulted, which prompted questions and a response from Mayweather: "It leaves me with great doubt as to the level of fairness I would be facing in the ring that night." The men went on to other battles: Pacquiao has fought nine times since the failed negotiations; Mayweather seven.

Champion fighters have long faced like-weighted challengers, partly out of pride. Boxers enjoy testing themselves, and by taking on the most worthy opponent and winning, an athlete can truly lay claim to the title of world champion, or even to the mythical title of all-time great. Professional boxers are called prize fighters for a reason: When two great fighters face each other there's a lot of money at stake, and Mayweather openly professes that he only fights for the money. But in the last decade there's been a frustrating shift in the upper echelons of the sport as individual business interests have gotten in the way of organizing the most compelling fights. The fight game isn’t centrally controlled, so boxers are essentially freelancers who look to their promoters to create fights and define their futures.

The initial failure to arrange the fight troubled fans, who wanted their own version of Ali-Frazier or Hagler-Hearns, two classic matchups that defined an era for the sport. At the time, Mayweather and Pacquiao were in their prime. But because premium boxers generally fight twice a year, and their events are held on pay-per-view television, there’s less of an incentive to take significant risks. Unlike most sports, in which a loss here or there is tolerated, losing a single fight can sink a fighter financially. In the intervening years after initial negotiations ended, Mayweather continued to win, and his record is now 47-0. Pacquiao won, too, but then lost a controversial split decision in one match and three years ago was knocked out cold by Juan Manuel Marquez.

But as Mayweather and Pacquiao’s pay-per-view numbers became less impressive, there emerged a stronger financial incentive to make the fight happen, even though it was becoming slightly less compelling as both men aged. Mayweather is 38; Pacquiao 36. As a boxer loses his reflexes, the consequences can be dire. (According to Compubox, the men have both started throwing fewer punches per round.) So when the fighters ran into each other at a Miami Heat game in January, they re-started the negotiating process.

The business of boxing is brutal, and there's tremendous infighting as the men behind the boxers strive for market supremacy. Top Rank, the company run by Pacquiao's promoter Arum, is considered the premier promotional outfit, and has a strong relationship with HBO, which broadcasts Pacquiao’s fights. In the other corner, Mayweather’s own company, Mayweather Promotions, has been trying to compete against Top Rank and has aligned itself with Showtime. Given the rival factions in the sport, the different parties often simply don’t want to do business with each other. The roadblocks in getting the Mayweather vs. Pacquiao fight organized, and the problems associated with the promotion of it, have only exacerbated the tension.

From the outset, Mayweather exercised his leverage: He's getting more of the financial split, and his team has been leading the often rocky promotion. For example, tickets went on sale only nine days before the fight. (Many went to the Mayweather team and are being re-sold in secondary markets for upwards of $10,000 per seat.) Arum lambasted the ticket situation and has been publicly feuding with MGM, specifically Richard Sturm, its president of entertainment and sports. Earlier this week, instead of Pacquiao doing a “grand arrival”—a branding event in which fighters are mobbed as they enter the hosting hotel’s lobby—Arum had Pacquiao skip the event to hold a “fan fest” at the Mandalay Bay, in a move meant as a slight to Sturm.

Instead of uniting boxing, the run up to Mayweather vs. Pacquiao has seemed to divide the sport even more. At the Wednesday press conference, Arum went out of his way to praise HBO and Mandalay Bay executives as Sturm and the Showtime executive Stephen Espinoza sat a few feet away. The boxing insiders in the room giggled at Arum’s various verbal digs, and even Mayweather seemed amused as Arum went on and on about HBO’s excellent programming. Leonard Ellerbe, the CEO of Mayweather Promotions, replied, “Bob, Showtime has the biggest star in sports and the best fighter in the world [Floyd Mayweather].” Espinoza defended Sturm, saying he'd “remained a gentlemen in the most trying of circumstances,” and tried to move the press conference back to the fighters.

Many members of the mainstream media, who'd never covered a major fight, looked baffled at what was happening on the stage.

Welcome to boxing.

For devout followers, the dysfunctional aspects actually make the sport entertaining, because it's an uncensored carnival quite unlike most modern corporatized leagues. But its lack of discipline also hurts its marketability to the general public.

So against all odds, the fight will be staged on Saturday. Mayweather vs. Pacquiao has become the Super Bowl of boxing, a defining moment for the sport that will cement the legacies of two all-time greats. If it’s a good fight, it could begin to smooth away the conflicts behind the scenes, or at least prove that the different factions in the sport can come together occasionally to create truly historic moments. For the duration of the match, at least, the fighting behind the scenes will be forgotten, and the stage will be handed to the athletes as the brilliant boxer from Grand Rapids takes on the beloved fighter with the quick hands from the Philippines.