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In the world of sports, few names are as synonymous with raw power and dominance as Mike Tyson.

But even the “Baddest Man on the Planet” has moments in his career that raise questions of “What if?” One such moment came during a particular stretch of his prime, when Tyson faced what could have been the greatest opportunity of his entire career—only to see it slip through his fingers.

The story centers around Tyson’s 1988 reign, when he was at his peak, reigning as the undisputed heavyweight champion. Tyson had annihilated opponents with seemingly effortless ferocity, securing a streak of knockout victories that made him virtually unbeatable in the ring. However, in a turn of events that has since become the subject of speculation, Tyson missed a crucial opportunity to solidify his legacy as perhaps the greatest heavyweight boxer of all time.

The Moment: The Lennox Lewis “What If?”
In 1988, Tyson was on top of the world, while Lennox Lewis, then an up-and-coming star, was beginning to make a name for himself. But while the two were on a collision course, Tyson’s management and personal issues interfered with the possibility of an early fight between them.

At the time, Tyson was considered the most feared fighter on the planet, and a showdown between the power-punching Tyson and the methodical, technically proficient Lewis could have been a defining moment in the sport’s history. Lewis, however, was not yet a household name in the same way Tyson was, and Tyson’s camp dismissed him as a threat, citing his age and inexperience.

In an alternate timeline where Tyson faced Lewis in the late 80s or early 90s, it’s conceivable that Tyson would have faced his most formidable opponent yet. Instead, Tyson lost his focus, went through personal turmoil, and ultimately lost the title in 1990 to Buster Douglas—an upset that shattered Tyson’s invincible aura. Lewis would go on to become one of the most decorated heavyweight champions of all time, but the window for a monumental fight against Tyson closed forever.

Tyson’s Words
In recent interviews, Tyson has expressed regret over missing that opportunity. “I didn’t know who Lennox was at the time, and I didn’t take him seriously,” Tyson admitted. “I was too caught up in my own world, and I missed a chance to face him when I was at my best.”

Had Tyson fought and defeated Lewis in the late 80s, his legacy might have been untouchable, solidifying his place as perhaps the greatest heavyweight ever. Instead, Tyson’s personal battles, a lost prime, and Lewis’ rise meant the greatest fight never happened.

The Lasting Impact
The “What If” of Tyson vs. Lewis in the late ’80s remains one of the most compelling questions in boxing. While Tyson’s reign may have ended earlier than expected, his influence on the sport remains immense. And while Lennox Lewis went on to cement his own legendary status, Tyson’s career continues to captivate fans with what could have been.

As we look back on Tyson’s career, it’s clear that his legacy was shaped by many factors—both in and out of the ring. But one thing is certain: in the realm of missed opportunities, the fight with Lennox Lewis stands as perhaps the greatest “what if” in boxing history