

Patrick Connor: Looking back at 'Sugar' Ray Leonard vs. 'Terrible' Terry Norris
Feb 10, 2026
6 min read
Ray Leonard was supposed to be different. Of course, he was still a unique figure and a great and incredible fighter.
But from the start he promised not to become a cautionary tale, not to follow in the footsteps of his heroes Muhammad Ali and Ray Robinson, both of whom ended up fighting on far too long.
Fourteen years after he won gold in the 1976 Olympics, Leonard announced he would be dropping back down to junior middleweight to take on the much younger “Terrible” Terry Norris at Madison Square Garden on February 9, 1991 — 35 years ago this week — and even the most optimistic reporters either couldn’t or wouldn’t avoid one of the sport’s most familiar tropes: The young feeding on the old.
Boxing’s ability to burn through fighters is legendary. In the 1910s, Chicago writer Ed W. Smith wrote of “the boxing gods” and their “mill,” which ground fighters out for the sport to consume. Nobody is immune to the gnashing teeth of the machine when the machine is boxing itself.
The reality is far more mundane: Fighters fight for money and pride. Leonard’s issue was he had plenty of both. His success in the Olympics turned him into a household name, and by the time the '80s rolled around Leonard was waiting with his Members Only jacket, a red Ferrari and matching leather boots. He wasn’t active in the ring and retired frequently because of his eye problems, but made enough comebacks to stay on the mind of most boxing fans.
To Leonard’s credit, he followed up his unexpected 1987 win over Marvelous Marvin Hagler with another surprise victory over Donny Lalonde before treading over old ground with Thomas Hearns and Roberto Duran. Few knew what to make of those fights, which saw Leonard struggle to get a draw with Hearns and sleepwalk to an easy win over a faded Duran. The only thing everyone knew was Leonard wasn’t getting any younger.
Even in his days as a fledgling pro, Leonard spoke of being hopelessly competitive at everything he did. He hated to lose and hated to look bad. And in his mind, making him look bad was exactly what these young guns were doing by encroaching on his success.
Terry Norris was just 23, and the only thing he lacked compared to Leonard at the same age was the Olympic gold. He was fast, powerful, athletic and good-looking. He trained just outside of San Diego and carried a 26-3 record.
One of Norris’ losses was a completely understandable knockout at the hands of Julian Jackson, one of the sport’s murderous punchers. Another was a loss in a welterweight tournament. The third loss was a more telling disqualification for hitting a downed opponent, which Norris just couldn’t seem to keep himself from doing throughout his career.
Norris put himself in a position to fight Leonard by scoring The Ring’s “KO of the Year” over John Mugabi in 1990. It was supposed to be a good fight. Mugabi was the Ugandan brawler who even forced Hagler back onto his heels, which virtually nobody did. So when Norris dispatched Mugabi in less than one round, it turned heads.
Leonard’s other options would have been to face WBA junior middleweight champion Jackson, a dangerous puncher who was struggling with his own eye issues, or the relatively unknown IBF champion Gianfranco Rosi. Norris’ availability, style and newfound popularity made him a clear choice.
The things Leonard said in interviews after the fight was announced lined up perfectly with dime-store psychoanalysis everyone always made about his career. Critics thought Leonard had a sterile and overly produced personality, that he was self-absorbed and obsessed with the past. He only seemed to confirm it when he said he saw himself in Norris. He knew Norris was younger, faster and hungrier, but he just wanted to see if he “belonged in boxing in the 90s.”
To Norris, Leonard represented more than just a direct path to money, fame and success in boxing. He was indeed similar to Leonard and he knew it. Worse, he found himself in the unenviable position of being brought in to execute an old hero.
“Ray’s my idol,” Norris told reporters. “He hasn’t stopped being my idol. I just have to cut it off for this fight.”
About five weeks before the fight, Leonard admitted to being knocked down in sparring for only the second time in his career. This time it was by a young 1-0 fighter named “Magic” Michael Ward, and a few days later he was badly hurt by welterweight Derwin Richards. Piling on was the issue of Leonard’s changing network allegiance.
Leonard’s star package included numerous appearances as a commentator for HBO Boxing since the late '70s, and many of his bigger fights appeared on the premium channel. This time Leonard had attorney and manager Mike Trainer handle the promotion, and the fight was to be televised on Showtime, HBO’s rival. This led to Leonard being ousted at HBO.
This all came about the same time that his divorce from wife Juanita was finalized, and yet somehow oddsmakers favored Leonard by about 2-to-1.
The opening round revealed plenty as Leonard fought tentatively and Norris chopped him up to the body. When Leonard settled in and threw hard to the body, Norris threw harder. When Leonard tried to flurry near the end of the round as he did against Hagler, Norris clipped him with a hard left-hook counter.
Norris fought carefully, but not scared. Leonard long ago solidified his reputation as a fighter who found ways to win and he openly tried to set traps, baiting Norris to step in so he could counter. Instead, in the closing moments of Round 2, Norris caught Leonard with another left hook as he leaned back, bracing himself with his gloves on the canvas. Without hesitation, Norris cleared several feet of canvas and punched Leonard as he was down, threatening to derail his own success once more.
Leonard didn’t even complain about the foul, and perennially inept referee Arthur Mercante Jr. issued a limp warning between rounds. It didn’t matter, because the message was both sent and received: Sugar Ray Leonard didn’t belong in a 1990s boxing ring.
Covering the bout for The Ring, Jeff Ryan wrote:
“Leonard lunged badly, firing amateurish haymakers he never threw even as an amateur. So desperate was he to find something that worked, he resorted to copying Vinny Pazienza by grabbing the top rope with his right hand and propelling himself forward to fire a left. But no matter what he did, Leonard couldn't cut off the ring on the shuffling Father Time, let alone the fleet-footed Terry Norris. The punches launched at Time couldn't graze the old man's beard. The ones aimed at Norris missed by a generation.”
Again in Round 7, Norris sent Leonard down by catching him in the middle of a combination. This time a right hand numbed his senses and Norris was thankfully stopped from going after Leonard again as he was down. Other times Leonard had risen from the canvas with a smile or a scowl. This time there was only a deep breath and a glance at his black shoes with white laces. But he did get up.
The former champ pulled himself together enough to perhaps win Round 8, though it was all relative. His best punches weren’t hurting Norris, who was avoiding most of them anyway. For whatever reason, the young gun didn’t press the issue and he settled for a wide unanimous decision as Leonard just slowly exhausted his own flame.
Not content to have the limelight stolen from him, Leonard once more announced his retirement to the crowd immediately after the fight. He later said, “It took this kind of fight to prove to me that it is no longer my time. I am not the fighter of the '90s.”
Fittingly, Leonard returned six years later at 40 only to be more violently sent into retirement.
At least Norris got in one last jab: “It turned out to be easier than I thought it would be.”
The boxing gods and their mill had the easiest victory of them all, however. Leonard became Ali and Robinson, and Norris soon followed.
Column

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