Yeah the Tyson win over Lewis in 95 is probably the least likely of the outcomes I chose for all those hypo fights that should have happened. But I was partially basing it on the fact that if I assumed 2 fights took place between Lewis and Tyson between 95-97 (which I did), that Tyson would catch Lewis with a big shot in one of the two contests and put him out. But certainly could see Lewis winning that one in 95.
Overall, the 90s were a very good era, but I can't help but being grossly disappointed when I think about how much better it could have been.
Really it has to be the most frustrating era in the history of the division in terms of the
fights that didn't happen (Bowe/Lewis, Bowe/Tyson),
fights that happened too late (Lewis/Tyson), and fights that I appreciated getting, but still wished they were earlier (Holy/Tyson and Holy/Lewis).
I mean if you think about the 70s for a second -
nearly every fight that should have happened did. We got 3 Ali/Frazier fights, the first of which was an almost ideal prime (Frazier) v. near prime (Ali) clash.
We got 2 Foreman/Frazier fights and 1 Foreman/Ali fight. Foreman was prime and Frazier and Ali were past prime but still formidable. The key though is that there is no way those fights could have happened sooner to match up better with Ali/Frazier's prime. Foreman simply hadn't come on the scene big enough yet to even have a chance of getting in the ring with Ali or Frazier from 71 or before, so no hope for getting a more prime Ali or Frazier. Point being I guess is that we have nothing to complain about with Foreman against those 2 in terms of the timing of the fights.
We got 3 Ali/Norton fights, and just like Foreman, no way could you match Norton up with Ali any earlier than they did for that first fight. So again no complaints as to the timing. We also got Foreman and Norton as well.
The only fight we missed was Frazier and Norton. In 77 or 78 a Holmes/Foreman clash was the other big event that was missed. So 2 fights missed out of getting nearly every other fight you could want as a boxing fan. I mean we even got Ali/Shavers, Holmes/Shavers, Holmes/Norton. Not much to complain about.
So the 70s were almost perfect in terms of the fights we got between the top guys, and the timing of them. Quite frankly the only fight from 75 and earlier that I really would have wanted to see is Ali/Frazier in 68 - but of course that didn't happen due to Ali's suspension.
Then look at the 80s era HW fights. Not a great era. But still we got Holmes/Cooney and Holmes/Witherspoon. I know Holmes missed some guys like Michael Dokes, Greg Page, and Pinklon Thomas. But missing those fights is a far cry from not getting Bowe/Lewis or Bowe/Tyson. Huge difference.
And then for Tyson's reign - he fought nearly everyone. In fact, I would say the 1 fight I wish would have happened during Tyson's run was a fight against Tim Witherspoon. Don't know when it would have been practical (maybe 86 on his way to the title?), but a
Tyson/Witherspoon clash is the 1 fight to me that was missed in the 80s. And I still wouldn't put that fight anywhere near as important as a Bowe/Lewis or Bowe/Tyson clash.
Then you have the 90s -
Holyfield/Tyson happens 5-7 years too late. Holyfield was ready for Tyson after beating Dokes in March of 1989. He was the clear no. 1 contender after that fight. He even offered a winner take all prize money just cause he wanted Tyson so bad. Then they finally sign in 90, all Tyson has to do is beat Douglas. Ugh. Then in 91 the fight is signed - and no opponents are in the way to screw it up. And then Elijiah Tillery ruins boxing fans by injuring Tyson's ribs in a sparring session 3 weeks before the fight. And alas a potentially epic Holyfield/Tyson clash in 89-91 didn't materialize. Instead we got their fight in 96 between two past prime, but still formidable HWs. A good and memorable fight of course, but still one can't help but imagine how much better both would have been a few years earlier.
Obviously
Bowe/Lewis was supposed to happen. Should have happened in 93 but Bowe/Newman ducked Lewis and took the easy money and easy victories. And then in early 95 it could have happened again but Lewis lost to McCall, thus screwing boxing fans again. Amazing that these 2 never fought against each other in the pros. Easily the biggest missed HW fight maybe ever (outside of a Holmes/Foreman clash in 78 perhaps).
We got Lewis/Tyson in 2002.
2002 - ridiculous. Great

we got to see a
badly faded/shot 234 pound Tyson fight a Lewis probably at the tail end of his prime - great for Lewis - bad for boxing. If we get this fight in 96, like we should have - things would be much clearer as to the historical standing of these two. A prime Lewis v. a past prime but still formidable Tyson - would have been interesting in 96. Anyway, one thing I can say about Lewis/Tyson is that it is IMPOSSIBLE to match up a prime Tyson against a prime Lewis since Tyson's prime ended with Spinks in 88, and Lewis wasn't prime till Morrison in 95. But still a 96 clash I would have taken.
Holyfield/Lewis we got in 99, 2 of them. Holyfield was past prime but still formidable, Lewis was prime. Lewis, as we know dominated Holyfield in the first fight with his jab and was robbed of the decision. The 2nd fight was damn close though, I have scored it for both men, though the last time I watched it, I watched several rounds multiple times, and I ended up thinking that Holyfield JUST edged out Lewis for the decision. But anyway, this fight certainly could and should have happened somewhere between 93-96. I think Holyfield would have won a UD over Lewis anytime before 96 (he would have a much better workrate than his 99', 36/37 yr old self, and would be the effective aggressor enough to get the decision over Lewis). Anyway, the 2 fights we did get were nice to have, but still should have happened earlier.
Lastly is
Bowe/Tyson. Much like Frazier/Norton, these 2 were reputed friends. Still they should have fought. I know Tyson was in prison. But they could have fought in late 95. Amazing that we never got to see this fight as I think it would have been a HW version of Hagler/Hearns.
Notice a theme running throughout though -
Tyson being in prison for 3 years really prevented the HW division from being as great as it could have been. With Tyson in jail, not many in the mainstream press thought the Bowe's and Holyfield's of the world were that great. And then Foreman beating Moorer in 94 really added to the PR perception at the time that the HW division wasn't that strong. A bogus perception I believe.
So you see if Tyson had not gone to prison - he legimitizes the whole division, especially if a Holyfield or Bowe beats him, they get instant credibility.
Actually though,
if just the Holy/Tyson clash goes off in 91, things would have been much better. Let's say Holyfield wins by late round TKO in a great fight (think 96 fight but less clinches, a better Tyson, and overall more action packed fight). Now let's say Tyson still goes to jail. Well the torch has been passed even with Tyson in prison. Now Holyfield is undisputed champ - he has beaten Tyson. Thus when Bowe beats Holy in 92 - Bowe looks even better, and the when Holyfield returns the favor in 93, and so on and so forth.
So you see how JUST the Holy/Tyson fight in 91 could have really improved the PR of the heavies in the 90s. And more importantly we as boxing fans would have gotten a prime (Holy) v. near prime (Tyson) clash that would have answered nearly every question out there about who was better. The 96 fight leaves too many excuses out there (legitimate or not) - Tyson was in prison for 3 years, Tyson was 8 years removed from best fight (Spinks), Tyson didn't take Holyfield seriously - thought he was shot, etc. A 91 clash removes almost all excuses no matter who wins. Tyson would be in top shape for a 91 Holyfield because Holyfield was the undefeated champion and Tyson knew from the 84 Olympics that Holy was tough.
But yeah let's just say the following 4 fights happen (since they were most likely to happen).
Holyfield/Tyson 1991
Bowe/Lewis in 1993
Bowe/Lewis rematch in 1995
Lewis/Tyson in 1996
Those above fights absolutely could and should have happened. Just imagine if they did, plus the fights we did get - 3 Bowe/Holyfield clashes.
If those fights had happened, the 90s would have been right there with the 70s. We as boxing fans would have gotten some potentially classic fights, and a lot more questions would have been answered about these 4 guys.
Thanks for the responses; good discussion.