Right in the thick of the Jail Blazers' era... he did a draft diary when we drafted Outlaw, making the joke about how we drafted Outlaw. Here, I went to the subject archive and found it.
From the 2003 draft diary:
6:25 -- Bilas just said, "The Sports Guy's running diary is very long." On the bright side, here come the Blazers! And there's a high schooler named "Outlaw" still on the board! And he has some baggage! This is too easy.
6:31 -- Yep, the Blazers take Outlaw. Unbelievably believable. That pick was so predictable that Tolbert had a joke ready for it. By the way, I wish I could buy stock in things like "Qyntel Woods and Zac Randolph will corrupt Outlaw before training camp ends."
I bolded the part that pissed me off. As far as I know, Outlaw was never in trouble when he was a kid. And as far as I know, Simmons literally made that up just to include it, knowing no one would call him on it because nobody cared about Portland or the High Schooler they had just drafted.
So, yeah, it's six years later and that still pisses me off.
Simmons is fun to read. I read every mailbag, chat, article, about half of his podcasts... but he's not a scout. He never played the game. He's wrong about half the time. When you realize that most of ESPN is now entertainment/comedy/general observations and not the expert opinions we all crave, you'll realize that Simmons is actually the best at it.
That said, I don't really care what he says. About anything.