Great question, I have always thought, and I'm a little biased I know, that Phil is grossly overrated as a coach. He certainly has the rings to back it up, but to me he is more a manager of personalities than an actual coach. Don't get me wrong, Phil has a niche and is very good at what he does, but at the end of the day the vaunted triangle offense was nothing more than get the ball to Michael or Kobe and get the hell out of the way. The triangle offense has no playbook, it is supposedly based on fluidity, motion and basketball IQ, what that really means is if you want the triangle and Phil Jackson to be successful, you need Michael Jordan, Scottie Pippen, Shaq and Kobe. The only transcendent superstar Pop has ever had, in their prime, has been Duncan. Imagine if Duncan had been able to pair with someone like Kobe or Lebron.
Hypothetically, if you gave Phil and Pop the exact same team to play against each other with, Pop wins those games more often then not in my opinion. I'll admit, I am know nowhere near enough to judge Red, which is why I left him out. However, in addition to Pop, I think Pat Riley is also better than Phil as well.