In an interview with RetroBoxingLive, Steward didn't hesitate when asked about the outcome. He said, "Muhammad Ali and Mike Tyson? Ali, Ali, Ali."
Steward, who trained boxing greats like Thomas Hearns, Lennox Lewis, and Wladimir Klitschko, explained his reasoning:
"Mike is one of the most amazing men and why I have so much respect for Mike Tyson is a small guy, I mean Mike is maybe about an inch, inch and a half taller than I am but I'm only 5'9, and the fact that he accomplished what he did was amazing and sometimes he lost when he fought big guys who were talented guys, who wasn't imtimidated by him, he always had a problem because he really was nothing but much more than a cruiserweight fighting these super-heavyweight's and so I think Ali would have won the fight because I thought he had too much boxing skills and physical size and just all around generalship and usually as the fight went on often times Mike as he tired physically and mentally he had problems in later rounds with those big guys and Ali actually fought better in the later rounds."
Steward acknowledged Tyson's incredible achievements despite his relatively small stature for a heavyweight. Tyson became the youngest world heavyweight champion in 1986 when he defeated Trevor Berbick. By 21, he was the undisputed champion, adding wins over WBA champion James Smith and IBF champion Tony Tucker to his record.
However, Steward pointed out that Tyson often struggled against bigger, talented opponents who weren't intimidated by him. He also noted that Tyson tended to tire both physically and mentally in later rounds.
On the other hand, Ali, standing as one of the greatest fighters of all time, changed the landscape of boxing multiple times during his career. A three-time world heavyweight champion, Ali defeated notable opponents like George Foreman, Ken Norton, and Joe Frazier.
Steward believed Ali's superior boxing skills, physical size advantage, overall generalship, and improved performance in later rounds would give him the edge over Tyson.
While this fantasy matchup will never happen in reality, it continues to spark debate among boxing fans. Both Ali and Tyson left indelible marks on the sport, inspiring generations of fighters and fans alike.