Now Larry Holmes was his most accomplished opponent but, wasn't what he used to be. Mitch Green wasn't afraid of him. But I would have to go out on a limb and say Tony Tucker. Not one of Tyson's more exciting fights at the time but he won the IBF heavyweight title from him over 12. Same with his previous opponent James Smith who was WBA champion. If If I can remember correctly I think Tucker won the early rounds.
Bonecrusher was trash aside from a big punch. Tucker's as good a choice as any. At the time Spinks was thought to be his biggest challenge, but we all saw how that went. So yeah, I agree with Tucker.
Bruno didn't go distance with Iron Mike though. He made it to a 5th rd stoppage after rocking Mike. Saw the fight twice actually. Tillis got knocked down but went the distance off his skills. Tillis was underated I think he fought like 3 future heavyweight champs. I agree with Green but I think Tucker was superior to him. Actually Tucker stopped Buster Douglas.
Holmes was out of the ring for years and completely out of shape when he fought Tyson. To this day, I can't believe anyone mentions it as a measure of anything. That fight was a joke. Quick Tillis still thinks he beat Tyson's ass, which is pretty cool.
It really depends on your criteria; If your asking who's Tyson's toughest opponent based on accomplishments or whats on paper versus who actually gave a valuable effort to beat a prime Tyson. As it relates to his "best" opponent on paper; I'd have to say Micheal Spinks. At the time Spinks was undefeated and he'd had two impressive, but controversial wins over Larry Holmes. Spinks, (the Lucain Bute before Lucain Bute) opted out of HBO unification tournament to fight a faded Gerry Cooney and I think the majority of fans gave him more of a chance at Tyson than some of the other opponents Mike faced in his prime. However, as we all would later find out, Spinks didn't put up much of an effort. As it relates to the actual fight; I'd have to agree with you and choose Tony Tucker or even a James Tillis that took a younger Iron Mike the distance, but that was before he became champion. So, my vote goes with Tucker; he managed to take Iron Mike the distance, he had his moments, and more importantly he was one of the first Tyson opponents to show some resistance.
On resume it must be Holmes and Spinks. But in practice my vote goes to Tony Tucker (IBF champion) and Tyrel Biggs (gold Olympic champion). - Two fighters who were undefeated and established when meeting Tyson. - Two fighters who had similar tactics/styles as Buster Douglas, but were far better fighters than Buster Douglas (Tucker TKO-ed Douglas 3 months before). And two fighters who were defeated by Tyson with ease! (don't tell me that Tyson struggled with Tucker just because he couldn't knock him out. It was a scorecard sweep. Besides Tucker went the distance with Lennox Lewis 6 years later in a WBC championship fight). People always ask what would've happened if a prime/trained Tyson would've showed up in Tokio against Buster Douglas. The answer lies in these two fights: - A trained Tyson would've won on scorecard sweep (ala Tucker) - A Tyson with a grudge would've knocked him out (ala Biggs). That's why I don't say Douglas exposed Tyson in Tokio; Tyson beat himself that night before entering that ring.
Pinklon had a great jab. Bruno and Ruddock were tough as well. But I agree with you guys Taking Tyson the distance was an accomplishment.