Wlad vs Tim Witherspoon.....

Both were legit top10 contenders by ring rankings. Whether you think they're crap or not is something else. Ibragimov was undefeated with wins over Briggs, Holyfield, Whitaker and Ahunanya. Not exactly great fighters, but they were all landslide decisions with barely dropping a round... and many people, classic posters here included, gave Holyfield a good chance.

Thompson was also undefeated, throws over 50 punches a round and has good wins over Guinn, Krasiniqi and T. Ibragimov.

How you can call them tomato cans is beyond me.

 

There is no logical reason for team Tyson to have avoided Spoon. Spoon was talented but not that much more talented then guys Tyson did fight and beat in the 80s.

 

Witherspoon did nothing during Tyson's reign to make him deserving of a title shot.

 

That too

Witherspoon did nothing to put himself in a position to even be avoided by Tyson. Tyson beat guys as talented or more talented then him in the 80s.

 

After Tyson beat Trevor Berbick for the WBC belt, he was slated to fight the winner of Witherspoon-Bonecrusher Smith for the WBA belt. Witherspoon missed out on his chance at Tyson by getting KO'd by Bonecrusher in round 1. After that Witherspoon was pretty inactive due to his problems with Don King. By the time Witherspoon got on track again, Tyson went to prison. You could make a case for a post prison Tyson avoiding Witherspoon, but not prime Tyson.
As for the question, I feel Klitchko with Manny Steward could work behind his jab and be vary wary of Tim's overhand right and win by a decision or late round TKO.

 

Bump

 

He survived Frank Bruno's hammers for a late round KO win. Tim's in the McCall-Mercer chin group. Tim has a chance, yes.