Alexandra Kometovna

Manny Pacquaio. The Filipino boxing champ and aspiring chessmaster catches up with an old friend

Alexandra Kometovna
Manny Pacquaio. The Filipino boxing champ and aspiring chessmaster catches up with an old friend

written by GEOFFREY GRAY
illustration by ADAM ROGERS

The biggest problem with Manny Pacquiao, according to his longtime trainer Freddie Roach, at least, is that he doesn’t sing anymore. Years ago, before he rocketed up Forbes’s list of the world’s highest paid athletes and became a rumored candidate for the presidency of the Phillippines, Pacquiao was a crooner. He played guitar, belted out karoake numbers. Love songs, mostly.

“It was a great way for him to relax,” Roach says.

Now, though, Pacquiao can’t breathe. He’s hardly ever alone. It’s unfair to say he keeps an entourage—his followers are more like a flock, filling every room in his home, every couch, every dining room chair. While Pacquiao makes a guaranteed $20 million per fight, it’s unclear how much he banks. For each fight, he spends roughly $2 million on tickets for his friends and family, inviting around 2,000 people to watch. Any day now, he’s slated to announce a fight with Floyd Mayweather Jr., an event that not only stands to be the most lucrative boxing match in history, but a global clash of morals.

Mayweather is a prodigious sinner. He’s been in prison for spousal abuse, espouses wealth over virtue, trash talk over compliments. Pacquiao has his foibles, but he’s chosen a path of piety. A few years ago, Pacquiao became a devout evangelical. Now his entourage includes priests and dozens of other believers who demand his presence at bible-study classes once, twice, sometimes three times a week.

Roach is fed up. “Just let the guy fight,” he says.

Pacquiao is not a fighter anymore, though. After growing up a street urchin in Manila and punching his way out of poverty, Pacquiao might be the most transformative global figure in boxing since Muhammad Ali. His smile alone—humble, boyish—inspires audiences around the world. In the Philippines, his nickname is “Ninong,” which means “godfather”. When we first met last year, I asked Pacquiao about Roach’s complaint that he doesn’t sing anymore. He didn’t feel inspired, he said, nor did he have the time. “Too many things to do,” he told me.

He has two main forms of relaxation, from what I gathered. The first is chess. After a sparring session last year, Pacquiao invited me back to his Los Angeles mansion to play a game. He drove a late-model Mercedes with a bodyguard; I followed with his flock.

When we arrived at his mansion, no less than seventy people were milling about. At the center of the living room there was a white throne-looking chair, its back of tufted white leather rising towards the ceiling. Still in his gym clothes, Pacquiao took his seat. Across the room, a keyboardist and singer were singing bible hymns and verses. Someone passed Pacquiao a microphone.

“My brothers and sisters,” Pacquiao said, addressing the crowd like a preacher. He talked about how he sidestepped the vices in life—wom-anizing, gambling, and drinking—and about his dreams, as if they were omens, keys to predicting the future. When he was done with his sermon, he beckoned me to his chessboard.


Pacquiao is an informed player. One member of his entourage is a Filipino chess master who accompanies Pacquiao during training to help him master the proper openings, sequences, and endgame strategies. Before we played, Pacquiao wanted me to take on his master first. Dozens of onlookers crowded around the board to watch the game. We slapped at a clock, and Pacquiao pawed at his goatee and raised his eyebrows and then rolled his eyes at the moves I was making. He played the master next and fared much better, quick to exploit weak moves, though cautious not to expose himself, like a boxer covering up.

Finally, it came time for us to play. We set up the pieces, and then the lights went out. A pair of guys appeared behind him. Pacquiao’s time was up. He rose, bid us good night, and disappeared up the stairs. The keyboardist packed up his gear; the chessmaster rolled up his chess board. Tomorrow would bring another performance, another lesson.

Pacquiao has so many obligations—he accepted an offer last year to work as a player-coach for a Filipino basketball team—his actual downtime is sparse. When he has a few days off, he likes to “vacation” in Israel. He’s gone so many times he’s even started to learn Hebrew.

On a recent Friday night, I sent him a text message, wishing him well. I didn’t know where in the world he was, or how many people were around him. I doubted he would write back. But then he did.

“Shabbat shalom my brother,” he said.