Evander Holyfield

With his outsized personality and ferocious punches, Mike Tyson cast a commanding shadow over boxing in the 1980s and ’90s. Meanwhile, Evander Holyfield endured years of delay for the opportunity to take down Tyson. The prevailing view of the mild-mannered Holyfield was that he was a journeyman – the heavyweight champion, but never a truly great one. Though Holyfield dramatically lost and recaptured the heavyweight crown, and then lost it again, even he understood that his career would ultimately be defined by how he stood up to Tyson – if he ever got his chance. By the time of their much-hyped and oft-delayed heavyweight title bout in November of 1996, Holyfield was 34 and considered past his prime. Four years younger, Tyson was heavily favored to be standing over another meek and easily vanquished opponent at the end. Instead, we got two of the sport’s most memorable fights – but for very different reasons.