Lets say that Lewis chose to fight on to the bitter end ala Holyfield. Who would his future oponents have been and when would time have caught up with him? To retain the WBC title he would have to fight various mandatories for that belt starting with VK. Regardles of the outcome of this fight VK would be retired due to injuries taking him out of the field for a few years. There would also have been a period between VK retiring and his brother rebuilding his career after the Brewster loss where the available competition would have been extremely weak.
Truthfully Janitor, I think he would have had tremendous pressure placed on him to give VK a rematch, and not only do I think that it was something Lennox DIDN"T want, but also feel that it was a fight he very well could have lost. To his credit, Lewis was smart enough to know his limitations and hence that it was time to call it quits. I love Evander Holyfield, but admit that he hasn't a fraction of Lewis's brains. Now, I DO FEEL that had he stuck around and put off the VK rematch, he likely would have had some payday opportunities against Chris Byrd, Wladimir Klitschko, and Corrie Sanders. While all would have been dangerous propositions for an aging Lewis, I do think he could have won all of the above fights, if he made a concerted effort to show up in the best possible condition that he could at age 38.
Someone would have caught Lennox, and stopped him for the L.Like Afterforementioned, he hasd the brains to check out at the right time.
Vitali would have fought Lewis and beat him (instead of fighting Sanders). Vitali would then retire because of his injury.. Sanders-Wladimir-Byrd-Peter would all be winable fights for Lennox, Vitali is the only man I'd favour to beat him in the mid 00s era. However age was starting to catch up with Lewis when he retired after beating Vitali (obviously a deserved victory for Lennox, but he was in deep trouble). So Sanders could have caught with a big shot and stopped him early, Wladimir could have defeated him with his youth and presicion, Byrd could have given the slower Lewis a tough time, and Peter, yeah same as Sanders. Lewis really retired at the right time.
38 year old heavies coming off a tough physical bout don't show up with their A game in their next bout. They are flat. That said, I think a Tyson rematch could have been sold to the public again & LL could have used that as his final bout. That way it would have been a big $$$ bout and really cemented a career and likely gone out on a no controversy type big ko in his final bout.
I reckon he loses to vitali. Sparks wlad in a crossroads fight then gets a rematch with vitali that he loses again. So all in all his legacy improves because he holds stoppage victories over the two greats that follow him and retains his beating everyone he fought record.