When The Two Greatest Boxers Fought Each Other

In 2007, The Ring ranked Henry Armstrong as the second greatest fighter of the last eighty years, noted Boxing historian Bert Sugar would also rank Armstrong as the second best fighter of all time. Of course we all know who was ranked as the no.1 fighter of all time – Sugar Ray Robinson.
So on August 27th of 1943 when Henry Armstrong challenged the rising star Sugar Ray Robinson, unknown at the time 15,371 fans would witness an event we will likely never again see in Boxing, the future no.1 ranked fighter in Boxing history against the future no.2 ranked fighter in history.

There was one sticking point to the fight. Sugar Ray Robinson did not want the fight. No it wasn’t because he was worried he might lose to Armstrong, it was because he just couldn’t find it within himself to fight the man he grew up idolising as a child, Henry Armstrong was Sugar Ray Robinson’s boyhood idol. No amount of money would convince Sugar Ray otherwise and Sugar Ray Robinson was arguably the first real business man in Boxing, demanding his own purses and share of the revenue. Floyd Mayweather Jnr may have earned himself the nickname ‘Money’ but it was Robinson who was the first real ‘Money’ man in Boxing.

Henry Armstrong tried to bait Robinson into the fight, calling Sugar Ray and gently prodding at the young Boxer that they would be a good match and would draw a lot of money. Robinson still refused to budge. Armstrong was put up to this by Boxing promoter Mike Jacobs. When this didn’t work, Jacobs took it upon himself to try and convince Sugar Ray into fighting Armstrong. Jacobs again mentioned how much money the fight would make. Again Sugar Ray was not
interested, but then Jacobs took another turn with the money angle and the penny dropped for Robinson. Pulling on his heart strings Mike Jacobs told Sugar Ray that Armstrong needed the money and would make more money fighting him than anybody else.
That was the turning point for Robinson, for now he knew if he didn’t fight his boyhood idol, he was denying Armstrong the chance to make a lot of money, to have one last big pay day to help him in life. He had to fight Armstrong for his own good, to help him earn a lot of money.
Sugar Ray though, had resolved not to hurt his opponent, knowing Armstrong was well past his prime he couldn’t bring himself to finish off his foe inside the ring. When the fight started, Robinson tested Armstrong with a few left jabs, Armstrong’s head snapped back. Robinson tested Armstrong further, this time with some right hands to the body, Robinson felt Armstrong sagging and just couldn’t hurt ‘an old man’ as he described the ageing Armstrong. Sugar Ray would carry his opponent throughout the fight, hitting Armstrong just enough to trouble him and then whenever he felt Armstrong sagging, Robinson would go into a clinch and hold him up, not wanting the man he admired to be embarrassed by a knockdown.
Sugar Ray Robinson would win every round en-route to an easy points win. In the dressing room after, a sportswriter mentioned to Armstrong it was too bad that Henry couldn’t have been with Sugar Ray when he was in his prime.
‘No,’ said Armstrong, ‘I couldn’t have handled Robinson on the best night I ever had.’

Armstrong knew the end was near, but he continued to fight for another 18 months before eventually deciding to retire having lost on points to Chester Slider. His last fight was on Valentines Day 1945 as he finally resigned himself to leaving the love of his life and hanged up his gloves at the age of just 32.
It was Hurricane Henry’s whirlwind fighting style that led many to believe he burned out relatively quicker, his high octane, fan friendly up tempo style of swarming his opponent under a barrage of constant and non stop punching meant he burned brightly but quickly.

Sugar Ray Robinson, as we all know, would continue his career and cement himself as not only the greatest welterweight in history(and quite possibly the greatest ever middleweight), but the greatest boxer of all time too. In an uncanny twist of fate, the love one man had for Armstrong – the best fighter of his generation, gave rise to the greatest boxer in history in Sugar Ray Robinson, later the love one man had for Robinson would give rise the greatest heavyweight in history – Muhammad Ali.

This article was an excerpt from my book ‘Forgotten Legends of the Ring‘ Available for download on Amazon.