The other day I was wondering about this. Would someone from "the old days" be an issue at all, since back then you could be so much more physical and get away with it?
I'll just never get why people think that a great player will make a great coach. Most great player relied on their rare combination of size and athleticism, not necessarily their brains. I would look for players that succeeded despite limited athleticism/size - Buck Williams, John Stockton.
There are smaller men who have great low post skills. Penny Hardaway used to kill in the post. Everyone says Kobe's one of the best. What about Mark Aguirre?
I think Olajuwan would be the best choice. He had the skills and he is interested in teaching big man skills. He has worked with Okafor, Howard, Yao Ming and Kobe and LeBron.
Oden did turn out pretty well offensively, but didn't he have a lot of offensive skills when we drafted him?
Sabas was a unique player - a 7' plus guy who could pass like a point guard and shoot 3's. Unlikely Leonard is in that class. But getting Laimbeer from the Wolves would sure be some poetic justice, even though I can't stand the dude.
I will be interested to see how Leonard's passing skills develop. In dead ball situations I routinely see him whip behind the back bounce passes right to the ref or a teammate. Very accurate. I wonder if he could learn to do that at game speed and if he has the vision and IQ to use it. I too would rather see a teacher come in rather than a talented NBA player. Having said that Olajuwan has had some success teaching players. Now way Leonard ever gets that quick, but maybe Olajuwan could help him use the athetic ability he has.