For the first 45 or so fights of what is now officially a hall-of-fame career, Manny Pacquiao relied almost exclusively on his speed and physicality and a crude-but-devastatingly effective southpaw left hand. That combination enabled him to overwhelm Lehlo Ledwaba, shock Marco Antonio Barrera, and drop Juan Manuel Marquez three times in the first round of their first encounter. It just wasn’t enough to stop a more cultured Marquez from fighting his way back into the contest over the subsequent 11 rounds, or to prevent Erik Morales from easing to victory in their first meeting.

Since hooking up with Pacquiao prior to the star-making bout with in June 2001, however, his trainer Freddie Roach had been attempting to add more tools to his fighter’s toolbox – an effort he intensified after that first Morales loss. A few rounds into his rematch with Morales, at the Thomas & Mack Center in Las Vegas in January 2006, it all clicked into place – after an even opening few frames, Pacquiao started working off his right jab and showing improved footwork and movement that enabled him to stop the Mexican icon in the 10th of a scheduled 12. Two fights later, he wiped out Morales inside three. 

The Filipino spent the rest of his career facing and defeating the very best in the business. Floyd Mayweather was the only one of his opponents to avoid defeat over the next decade. But he was at his devastating best over the four years that followed the Morales rematch, as he moved up in weight and blasted one opponent after another into concussive defeat. His one-punch obliteration of Ricky Hatton and his ferocious turning back of Miguel Cotto were perhaps the apotheosis of that run, but immediately before those two he turned in a spectacular performance against a fighter who, a decade earlier, had himself been the one marching through weight divisions and turning back quality opposition.

The notion of Pacquiao, whose only appearance above 130lbs had come in his battering of lightweight titlist David Diaz in June 2008, taking on Oscar De La Hoya, who had recently battled Floyd Mayweather to a split decision at 154lbs, was the brainchild of HBO analyst Larry Merchant. Following the loss to Mayweather, De La Hoya’s career ledger stood at 38-5, and the Golden Boy, pushing 35 years old, planned to bow out after a closing trilogy of fights in 2008. The first of those bouts involved him dropping back to 150lbs to take on former 130lbs titlist Steve Forbes, but although he won a clear decision, he was badly marked up in the process and clearly struggled to make the weight. That should have been a flashing red light, but when a rematch with Mayweather fell through when the latter announced his (temporary) retirement, and bouts with Hatton and Cotto failed to materialize, he zeroed in on the contest with Pacquiao, which was set for December 6, 2008.

For most of us ringside that night, it was a mismatch of the highest order. Sitting in the lobby bar at the MGM Grand two nights before, I told a fellow writer, who was canvassing opinions for a final pre-fight column, that I saw no way the smaller man could prevail. Unless, I added almost off-handedly, it transpired that De La Hoya was suddenly shot.

That was exactly what Roach expected, asserting that De La Hoya, whom he had previously briefly trained, could no longer pull the trigger. He accepted the match-up, even though Pacquiao had only once weighed in within 12lbs of the contracted 147lbs weight limit, for that very reason – confident that it would send Pacquiao’s already-burgeoning profile into the stratosphere.

The first concrete sign that Roach was on to something came at the weigh-in. Pacquiao, unsurprisingly, tipped the scales comfortably inside the limit at 142lbs. De La Hoya, more surprisingly, was only three pounds heavier, at 145. The expectation was that, come fight night, the Golden Boy would be a middleweight; instead, he put on a grand total of just two pounds – or perhaps less, given that he weighed in on Friday in his underwear and stepped on the unofficial HBO fight-night scale in a sweatsuit and shoes.

Pacquiao would be the shorter man on fight night, but he would be the heavier one, and when the fighters stood center ring for referee Tony Weeks’ final instructions, Roach noticed what appeared to be IV injection marks on the Golden Boy’s arm, a tell-tale sign that he had been struggling to rehydrate. He smiled to himself, more confident than ever that victory was theirs if Pacquiao followed the game plan.

That game plan became evident early on. From the opening bell, the Filipino showed speed and energy, darting in and out, flashing a jab and landing the first meaningful punch of the fight after 60 seconds had elapsed, in the form of a straight left that landed flush on De La Hoya’s face. Twenty-five seconds later, Pacquiao landed another, and meanwhile De La Hoya stood and watched, seemingly confused by what was in front of him. Outside of a left hook to the body and some tentative jabs, De La Hoya’s only offense in the opening frame was a pair of half-hearted flurries that largely missed their target. Somehow, the judge Stanley Christodolou scored the round for De La Hoya; it would be the only round that he or either of the two other ringside officials would put in the Golden Boy’s column.

A straight left from Pacquiao landed behind a jab in round two, and a lead left followed. A couple of hooks from De La Hoya to the body were slow, sweeping and wide. Already, De La Hoya’s face was carrying a couple of red marks. Now Pacquiao turned to his body, before switching to a right uppercut. Another lead left landed as the constantly circling and moving Pacquiao left the Golden Boy looking mesmerized. “Pacquiao has neutralized De La Hoya’s left hand, which was one of the best weapons in boxing for more than a decade,” noted Merchant on the HBO pay-per-view telecast.

De la Hoya’s strengths had always been his stiff jab and his left hook; through the opening pair of stanzas, however, he had landed just six of 56 attempted jabs and his hook was nowhere to be seen. In contrast to the constant motion of Pacquiao, De La Hoya was showing no upper-body movement, standing straight up and following his foe as he turned and twisted over the canvas. He did attempt a wide left hook to the body, but Pacquiao bounced away and into center ring and landed another lead left on Oscar’s nose. 

De La Hoya opened the fourth with a right hand that Pacquiao slipped, after which the Filipino turned De La Hoya around and launched a flurry. Pacquiao was now starting to open up more, stabbing a right to the body and then a left to the side of De La Hoya’s jaw. Another quick three-punch combination was followed by a brief pause and then a left hand. 

The pre-fight narrative had been ripped to shreds and an entirely new one was emerging.

“Oscar has another eight rounds left to prove whether he is still a prizefighter,” offered Merchant. In round four, Pacquiao landed 32 of 47 power punches; De La Hoya just 8 of 20.

“He can’t handle your speed, son,” Roach told Pacquiao in the corner after the fourth.

Truth be told, De La Hoya couldn’t handle anything Pacquiao had to offer. A left hand followed by a straight right presented De La Hoya with a new challenge and one that he failed as the Filipino’s punches rattled off his head. One, two, three right jabs landed, then another couple as Pacquiao turned De La Hoya again. Slowly but surely Pacquiao was turning up the heat, unleashing more combinations and stepping into them with greater authority, physically moving De La Hoya with each combination. De La Hoya did at least throw 65 power punches in the fifth, prompting Nacho Beristain to declare enthusiastically, “Mucho mejor”, as his charge returned to the stool. But in reality, it wasn’t even a false dawn. The worst was yet to come.

For the first five rounds, De La Hoya had been attempting to march Pacquiao down and back him to the ropes, but beginning with the sixth, he started to retreat. Perhaps, mused Merchant, De La Hoya was switching up strategies to try and catch Pacquiao coming in. But as much as anything, he simply appeared lost and on the road to being beaten, as his left eye started to swell and darken ominously.

De La Hoya landed a straight right to kick off the seventh, but Pacquiao slid out of the way before he could wind up to throw another. De La Hoya now was in full retreat, not out of strategy but out of helplessness; Pacquiao backed him in to a corner, swarmed him, moved out again, saw that De La Hoya had nothing to offer in return, and moved back in to unload again. 

“Manny Pacquiao is annihilating Oscar De La Hoya,” said HBO commentator Jim Lampley. “And De La Hoya has zero answers for the Pacquiao assault.” Pacquiao was unloading now, but not recklessly, pausing after each combination to examine its impacts on his opponent, judge whether there would be any incoming return fire, and resuming his assault when it became clear there wouldn’t. Lefts and rights were landing flush, and De La Hoya was powerless to do anything about any of them. His left eye was blackened and swollen almost shut.

“An embarrassing seventh round comes to a close,” said Lampley, before clarifying. “Embarrassing for De La hoya. Exciting for Pacquiao.” All three judges saw the shellacking as a 10-8 round.

“If you don’t throw punches,” Beristain warned between rounds, “we’re going to stop the fight”.

As he came out for the next round, Pacquiao appeared almost embarrassed by the one-sided beating, and the eighth saw him seemingly take his foot off the gas just a little before a multitude of blows at round’s end rattled De La Hoya. The Golden Boy was looking lost and it was just a question of whether Pacquiao wanted to apply the coup de grace.

In the event, he didn’t need to. 

“It could be that the curtain is drawing on the long and glorious run of the Golden Boy here tonight,” opined Lampley, and after both the ringside physician and Weeks advised De La Hoya that if he continued to absorb punches they would have to stop the fight, Beristain made the decision for everyone and pulled his man from the contest. 

De La Hoya immediately stood up, walked toward Pacquiao and embraced him.

“You’re still my idol,” said an emotional Pacquiao.

“No, you’re my idol,” replied De La Hoya.

“We knew we had him after the first round,” Roach said afterwards. “He had no legs, he was hesitant, and he was shot.”

“Freddie, you’re right,” De La Hoya told Roach. “I just don’t have it anymore.”

Some years later, after multiple issues with alcohol and drug use, the Golden Boy would confess that he already knew he was a beaten man well before he stepped into the ring. His camp for the Pacquiao fight, he admitted, was the first time he showed up to training drunk.

Four months later, De La Hoya announced his retirement with a career record of 39-6 (30 KOs). He was inducted into the International Boxing Hall of Fame in his first year of eligibility, in 2014.

Pacquiao marched on, knocking out Hatton and Cotto before entering into a slow, and decidedly relative, decline, going almost nine years without a stoppage win and seeing victories over the likes of Antonio Margarito, Shane Mosley, Tim Bradley, and Chris Algieri interspersed with losses to Mayweather, Bradley, Marquez (at the fourth time of asking, by spectacular knockout), and even Jeff Horn before, at the age of 42, himself taking a career-ending beating from Yordenis Ugas.

Pacquiao retired after the Ugas bout with a record of 62-8-2 (39 KOs) and world titles in multiple weight divisions; and, despite repeated rumors to the contrary, he has resisted the urge to return in a sanctioned fight. And now he too is officially what he was clearly destined to be on that night 16 years ago: a hall of famer.

Kieran Mulvaney has written, broadcast and podcasted about boxing for HBO, Showtime, ESPN and Reuters, among other outlets. He also writes regularly for National Geographic, has written several books on the Arctic and Antarctic, and is at his happiest hanging out with wild polar bears. His website is www.kieranmulvaney.com.