"I like to think I would be, just for the fact that I guard the post, I guard the ball," Green told NBA.com's Steve Aschburner when asked whether he would be as great a defender 25 years ago as he is today. "I like to think I’d have found a way. But having said that, I’m not sure I would have been able to guard Shaquille O’Neal. I’m not sure I would have been able to guard Hakeem Olajuwon. I’m not crazy enough to begin to say, 'Yeah, I could have stopped Shaq.' But if I couldn’t, I guess I fit into a category with a bunch of other people."
Two of the greatest big men of all time, O'Neal and Olajuwon were absolutely dominant during their time. O'Neal might be the most physically imposing player the NBA has ever seen, and Olajuwon's post moves were transcendent for his time.
Draymond would have a significant size mismatch against O'Neal, as Shaq checked in at 7-foot-1 and 325 pounds. Green is listed at 6-foot-6, 230 pounds this season.
Olajuwon was another 7-footer who had elite athleticism, although he weighed in at just 255 pounds. Draymond likely has picked up some tips from Hakeem on the defensive end, as Olajuwon is a two-time DPOY and led the NBA in blocks three times.
Green certainly believes he could defend whoever lines up across from him, and his resume backs that up. But Green also has respect for the legends that came before him, and Shaq and Hakeem are two of the most difficult centers to defend in league history.
Until we have time travel, however, we won't ever be able to see an actual matchup between Green and the two big men in their respective primes.