Some of these guys were just not as good as they (and others) thought/think they were. So often more a case of "overestimating" themselves or being "overestimated" THAN an underestimation of the other guy.
There was talk Don Curry had on the table a multi million dollar offer for a showdown with Marvin Hagler. Instead he took a fight with Lloyd Honeyghan and what was supposed to be a routine fight turned into a brutal beating.
That is incorrect about Tyson. He did schedule the fight with Holyfield but pulled out due to a training injury. Holyfield fought Cooper instead.
Bobby Czyz and Alex Ramos . Both had big pay days waiting for them with Marvin Hagler (In hind site, it was a blessing they lost early, Hagler would've destroyed them.) Davey Moore also was being groomed for a title shot against Hagler, a old guy with the last name of Duran had something to do with closing that door.
Your username disappeared and everything. I made an entire thread https://www.boxingforum24.com/threads/anyone-know-what-happened-to-unforgiven.632827/
That doesn't change the fact that he blew a big money fight with Holyfield, by losing to Douglas. He was under no pressure to take the Douglas fight!
That was in 1991 and is correct. However, Tyson-Holyfield was first scheduled for June 1990. June 16th, I think. But the Douglas loss scuttled that one. As far as Tyson being under no pressure to take the Douglas fight, he'd already cancelled a late 1989 bout with Razor Ruddock. I think he'd cancelled or postponed others in 88 & 89 in the aftermath of kayoing Spinks. So I'd imagine there was at least a little of "Mike, you can't keep pulling out of fights" from Don King.
Yeah, it was set up for after Douglas, but ultimately the court case is what prevented the fight. Stewart, two Ruddock fights, and a match match with Holyfield would've paid a whole lot, so the loss to Douglas in itself didn't prevent Tyson from getting huge purses.