Fitz would frustrate him early but I think Tyson eventually catches him with a combo and puts him to sleep. Similar to the Mathis Jr fight.
Mike Tyson from 1988 KOs (or TKOs) ANY fighter in history except the 60s Ali. That's right... he KOs Foreman, Frazier, Louis, Holmes, Marciano, Lewis, Johnson, Dempsey, Bowe, Holyfield, Liston, Patterson, Jeffries, Greb, Charles, Moore, Tunney etc. And I'm not even a huge fan of Tyson. It's just when you see in his prime, when he could slip and counter almost anything his opponents threw, and his counter-punches could knock you out cold. He was unbelievable. All the hype was NOT false (well, not entirely). I think we can all agree Dempsey, Louis, Frazier, Patterson, Johnson and Lewis aren't going the distance. The rest I mentioned are a harder job for Tyson but I think the '86-'88 version can do it.
Mike Tyson via unadulterated and utter destruction. Bob Fitzsimmons may have been excellent at knocking out your local bully and street tough, but a young Tyson was in another world compared to those men. See Tyson vs M. Frazier for more details: This content is protected Quite frankly, I think even a 15-17 year old Mike Tyson would have destroyed, annihilated and decimated many of those guys back then. Especially with those tiny, horse haired gloves.
And even from Louis time, I'd say that only Joe Louis himself and at his peak performance would have a chance at taming a prime Tyson and even then, he may have to escape a few close calls to do it.
BOILERMAKER you give a sober analyses & despite the Old School nickname attempt to be fair The large majority you argue is correct_still your conclusion is way off I believe eras are not as similar as you think_but more equal than some assume Still that is a small difference Also boxing may well be the rare sport where at least from a certain time on like the last ninety years roughly the average quality may not have changed much pound for pound Modern era advantages may be balanced fully by more fights against all comers & some now more obscure skills even body punching But first Fitz was not such a combination puncher like many later & Tyson Still you may think he has a chance with his trap setting>>> But man you can look at him or his stats: he was at most a SMW! He was not shorter than Tyson but prime Tyson outweighed him by a full fifty pounds Lean meaning almost all muscle The best he could do is tough it out & MAYBE a Hail Mary could drop Tyson surprised by his power & lax on defense But it is hard to see Ruby Red as he was as better than a fifty to one shot> At best A hundred to one is more realistic