The thing is, if he stands toe-to-toe with a prime Mike Tyson he's taking a risk but he's also going to be putting some serious hurting back on Tyson. It's not like he ran and held when they did eventually fight.
I just dont rate Tyson's ability to take a sustained series of punches, he couldn't fight going back, and Holyfield's punches weren't bee stings.
Ruddock landed harder accurate punches on Tyson and it did nothing. You seem to think the Tyson of 96 is the same as the Tyson of 88 or 90 again.. Holyfield didnt hurt Tyson that much in 96 until late in the fight when Tyson was pretty dam exhausted. He still couldnt get him off his feet when he was defenseless.
Your also putting too much emphasis on backing Tyson up. Noone backed Tyson up at his best. He backed up against Holyfield because he wasnt the same fighter. Douglas didnt back him up, he just beat him to the punch and kept him at distance with good footwork and jab. As much as Holyfield underestimated Cooper like you say, Tyson underestimated Douglas. You seem to give Holyfield a pass for his poor performances but Tysons were all keys to how one dimensional he was.
Holyfield had George Benton with him in the period we're discussing.
I think you're quick to notice Holyfield being "recakless" or "careless" at certain times against Foreman, for example, BUT he brawled a similar amount (to the Foreman fight) against Bowe in the rematch too (under Steward).
Not to mention the third Bowe fight where Holyfield was trading too much, and got himself stopped in 8 rounds (under Don Turner and Tommy Brooks).
He still fought a more controlled fight and just like in the Foreman fight, he was more effective when he boxed, but he still brawled in both, was hurt at one point against the slower Foreman, and barely won the rematch with Bowe because of it, It was his nature, and Im sure Steward would have liked Holy to box more but Tyson made everyone brawl, run, or hold and the Holyfield of 90 would have brawled or been prepared for the fight with Tyson like he was in 96 under Duva and Benton.
Tommy Brooks was an assitant to Turner, he didnt take full charge of Holyfield until the Tyson fight, where he brought in specific sparring partners and prepared Holyfield a specific way.