He knows just about everybody, he has agent sources for sure, a lot of them particularly at CAA, a couple GMs (Morey notably), people in the league office, etc. etc.Is Simmons even that tied into the league anymore? It feels like his contacts and pals are now more in his line of work - content creation - than playing, coaching or front office roles. That likely means he still has better color than us ham and eggers however maybe he isn't as connected as he was a few years ago.
If anything I'd say he's more connected now than he was at ESPN because he's got a lot more money and he's expanded his brand. He's hinted at stuff often that was accurate, and his "guesses" are often things he knows but isn't "reporting" like Ishbia, he was one of the first I saw on that, even had the price weeks before any actual reporting came out.