'Sugar' Ray Robinson's toughest opponent was Gene Fullmer whom he also lost more than twice
http://www.boxing.com/brawls_and_bruises...
Jake LaMatta and Carmon Basilio tie for a close 2nd
Great question and 2 ways to answer this as well.
Robinson's toughest opponent? Several guys gave him all kinds of trouble in the ring. The first was Jake LaMotta who gave Robinson his first career defeat. Then Robinson went on an incredible win streak before being upset by Randolph Turpin. Then he had a series of fights with Carmen Basillio who beat Robinson for his title and regained it from Basillio in another extremely tough fight. Gene Fullmer who was a brutally strong man beat Robinson, was knocked out by Robinson with a perfect punch in the rematch, then the last fight was declared a draw. So out of those fighters I would say Carmen Basillio was his toughest opponent.
Toughest fighter that Robinson ever fought? One of the toughest fighters of all time was undoubtedbly Henry Armstrong who was a perpetual punching machine with great stamina and rock solid chin and is highly regarded as one of the top 5 greatest fighters in boxing history. When Robison beat Homicide Hank, Armstrong was past his prime and not as great of a fighter as he had been.
Jake Lamotta because he was a bad style match up. Lamotta was the only man to beat prime Robinson.
With that said; the best opponent that he lost to that was in his prime was Kid Gavilan [who is 1 of the best welterweights ever]. Gavilan style wasn't a nightmare for Robinson like Lamotta, but Gavilan was better than Lamotta at the time [kind of how Corrales was better than Castillo but Castillo gave Mayweather problems, unlike Corrales].
The highest ranked fighter Robinson fought was Henry Armstrong who was past his prime.
Robinson lost to Fullmer more than twice but Robinson was way past it by this time.
Jake LaMotta.
I gotta give Henry Armstrong that honor, with no disrespect to Jake LaMotta or Carmine Basilio (two of the toughest to ever lace up the gloves) Armstrong was tougher.
Jake Lamotta was his biggest rival and probably amongst the toughest of fights he had.
Jake Lamotta is the most noteable
All in union say, JAKE LaMOTTA. they were meant to fight each other.
I'd say it's Carmen Basilio.
Jake Lamotta, Randolph Turpin , Paul Pender who he lost to twice.
