My greatest what if is what if Roberto Clemente hadn't died in a plane crash. He still had 4-5 good years left. He was the best player in baseball in 1971. He struggled with injuries in 1972. A healthy year in 1973 and the Pirates easily with the division and have a strong chance at another World Championship and future runs at least in 1974-1975.
I feel he is one of the most underrated players ever. Give him ~5 more years of counting stats, more gold gloves and rings and maybe he gets the respect today that he had at the time, as the best player in baseball in the late 60s-early 70s and his place as one of the greatest all around players ever.
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