Oakley was overrated and underrated at the same time. Overrated because he was a rebounder, banger, enforcer during the last era, when scoring was down and games were slower and more physical, so his skills were valuable. It’s a more wide-open game now. If he played today, teams would just go small and force him to guard a perimeter player; he wouldn’t be able to do it, and he wouldn’t be able to make the smaller guy pay on the other end. And he couldn’t shoot threes and stretch defenses like a Charlie Villanueva does, so he’d be essentially useless. We know this because there are no successful power forwards with Oakley’s game right now. They’ve all been drummed out of the league. He’d be a role player at best.
On the other hand, he never got enough credit for basically being the real-life Shaft — the coolest guy in the league, as well as the toughest — which is a point I argue vehemently in my book, and threw in a firsthand story as evidence. You couldn’t have played Rileyball in New York without Oakley. He had to be there as the bouncer in the bar, so to speak. Oakley was so cool that MJ adopted him as his real-life enforcer. What does that tell you? - Bill Simmon