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The year is 1950. Boxer Sugar Ray Robinson is 29 years old, in the midst of a 91-fight unbeaten streak, and reigns as world welterweight champion. Dressed impeccably, he leans casually against his pink Cadillac, which sits parked in front of two of his businesses, and reads a letter.
Though renowned for his boxing exploits, Robinson was also an entertainer as comfortable mingling with Hollywood stars as he was moving across the ring.
In the photograph below, we see the man widely considered to be the greatest boxer of all time in action (connecting with Jake LaMotta’s head at Madison Square Garden in February 1945, in the fourth of six fights in their epic rivalry). Muhammad Ali spoke reverently of him: “That man was beautiful. Timing, speed, reflexes, rhythms, body, everything was beautiful.”
More than any other fighter who came before or since, Robinson embodied the sport of boxing, and his career became the prototype of the modern athlete. He owned the rights to all of his fights, and he became a businessman and owner, among other things, of the dazzling Sugar Ray’s nightclub, which hosted the biggest stars in entertainment.
And Robinson’s life was deeply symbolic. According to journalist Herb Boyd, his vibrance and achievement mirrored the revitalization and eventual decline of Harlem, the historically Black neighborhood that he emerged out of: “When he was in his glory days, Harlem was revived. When he began to decline, his career went to shambles; so did Harlem.”

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Robinson was born Walker Smith, Jr. on May 3, 1921 in Ailey, Georgia to Walker Smith, Sr. and Leila Hurst. He was the youngest of three children. Poor farmers in Georgia, the Smith family joined the great exodus of African Americans out of the South and into Northern industrial cities. Smith, Sr. moved to Detroit, found work in construction, then called for his family to join him. When the marriage dissolved, his mother relocated to New York and Smith, Jr. grew up in Harlem.
It was as a member of the Harlem-based Salem Crescent Athletic Club that a 12-year-old Walker Smith, Jr., discovered his talent and love for boxing. It was also where he gained his professional name when, after begging his coach for the opportunity to compete against a rival club, he was randomly assigned an amateur boxing ID. Thus Smith, Jr. became “Ray Robinson.”
It was during his illustrious amateur career that Robinson gained the nickname “Sugar” for his skill and dynamism in the ring. Later fighters, including legends like Ray Leonard and Shane Mosely, would take on the moniker in testament to their skills and in homage to their forebearer.
During a short stint in the Army between 1943-44, he traveled alongside heavyweight champion Joe Louis and other professional fighters and performed in exhibition matches.

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However, unlike Louis, next to whom he stands in the photograph above, Robinson was much less committed to the military cause; after disappearing from the barracks for several days and missing a ship to Europe, Robinson woke up in a military hospital claiming to have no memory of how he got there.
Military authorities claimed he suffered a “mental deficiency,” and he was honorably discharged. Undeterred by accusations of desertion, his career continued apace. He won the welterweight title in 1946.
Robinson’s passion for boxing markedly declined after his 1947 bout with Jimmy Doyle, who died from severe head injuries the day after the fight. Walking into the fight with an almost debilitating sense of foreboding that tragedy would strike Doyle, Robinson initially wanted to cancel.
Convinced to go on, he was tested in the seventh round when Doyle staggered him twice and cut him over his left eye. Robinson gathered himself to meet this onslaught and, in the eighth round, landed a counter right that shattered Doyle.
The champion walked away with the 79th victory of his career; the challenger was carried from the ring with the aid of Robinson’s manager George Gainford (below center, wearing the white T-shirt with Sugar Ray on the back) and rushed to a nearby hospital, where he never regained consciousness. Here was the physical cost at the heart of prize fighting.

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Despite Doyle’s death, Robinson continued to box. In 1951 he fought middleweight champion Jake LaMotta for the sixth and final time. The bout, known as “The St. Valentine’s Day Massacre,” was a brutal affair. Robinson controlled the pace through the early rounds before LaMotta came alive in the 11th, catching Robinson along the ropes.
This marked the champion’s last stand. In the final two rounds Robinson savaged LaMotta, who offered little resistance. Here we can see Robinson in the final round of the fight pressing the attack against his devastated rival en route to winning the middleweight championship via stoppage.

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After this astounding victory, Robinson, along with his Cadillac and entourage, embarked on a European tour during which he met the president of France and made several title defenses.
In 1951, he stood proudly in the photograph below, having just been awarded the Benny Leonard Good Sportsmanship Trophy at the end of his glorious 1951 campaign during which he went 9-1-1, having defeated LaMotta to claim the middleweight crown and avenging his only loss in knockout fashion to reclaim his titles.
During the ceremony, he was lauded as a “champion among boxers and men.” That same year Ring Magazine named him “Fighter of the Year” for the second time. He was at the apex of his career.

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While Robinson had a dazzling smile and gregarious personality, the punishment he inflicted on his opponents in the ring was often felt by those closest to him outside of it.
His constant philandering, the abuse he inflicted on his romantic partners, particularly his second wife Edna Mae with whom he is pictured here along with his son Ray Robinson, Jr., and his lack of presence in his children’s lives created deep and lasting wounds.

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He fought long past his prime, in large part to pay off back taxes. By the time he retired at the age of 45 in 1965 his halcyon days were over half a decade past. Despite his vast career earnings, his lavish lifestyle, poor investments, and trouble with the IRS drained him. A second career as an entertainer never panned out.
By 1965 he was broke and spent the rest of his life struggling to stay afloat.
It was a long way down from his glory days, when, in 1950, he leaned so confidently against his pink Cadillac.

Learn More:
Remembering Sugar Ray: Edna Mae Robinson Recalls the Glittering Pain of Her Past
Harlem’s Sugar Ray Robinson’s Sweet Success
“A Brooding Genius” by Larry Schwartz
“Sugar Ray’s Harlem, Back in the Day” by Corey Kilgannon
Sweet Thunder: The Life and Times of Sugar Ray Robinson by Wil Haygood
Muhammad Ali On Sugar Ray Robinson
Harlem, NY- “Sugar Ray Robinson Way” Ceremonial Street Sign Unveiling
Rewind to 1951: The St. Valentine’s Day Massacre by Nick Parkinson
Jake LaMotta vs Sugar Ray Robinson 6 // “St. Valentine’s Day Massacre” (Highlights)


