One of the things I took note of in the 30 for 30 was the sort of outsider, poverty mentality that has fueled Cal his whole career. What I mean by that is that there is a sense that he's not part of the tribe, that at any point he may be excluded from the tribe, and that you should take what the tribe has to offer you today before it discovers you're not part of it and kicks you out. This, in some cases is good because you don't lose sight of what you need to survive long-term, but it also could lead to some shortsighted decision-making.
Before I watched the documentary, I had a couple different theories about why he pushed out the door so fast. One was that he needed to be seen as a players' coach so it was really marketing so that he could continue to recruit at a high level. The other theory I had was that he was really only chasing stars so by pushing them out the door he had more slots to bring in other potential stars. I now lean toward the more kind theory that says he believes this is what is best for the kids. But that doesn't mean that he always knows best, nor does any coach.
So when Roy Williams time and again convinces a kid to stick around for an extra year, it's clear that's in Roy's best interest. When Cal convinces a kid like Daniel Orton to leave to take late 1st round money, he believes it's in the kid's best interest, but it's possible that's not true. It's possible that his particular worldview is great for some kids and damaging for others. Daniel Orton might've developed far enough in his sophomore season that not only would he have been chosen higher, but he also would've been better prepared to contribute right away and would've scored more than 143 points total in his NBA career and wouldn't be playing in Lebanon now.
I guess what I'm saying is that I don't think it's as zero-sum as many people do. There are a wide range of outcomes in any decision and while there's no question that in most cases Cal is doing what's best for the player, it's also possible that in some cases his worldview influences him to push something that's both worse for the player and UK. I'm glad that he's done that because if he kept 1-2 more players a year, it would be terrifying to go up against you, but that's just not how he sees the world.