I think Bill Simmons is entertaining, but I'm not sure that he's great to pair with a real statistician. He makes a million assertions a minute. I guess Simmons has done a decent job of interviewing statistical experts at the MIT Sloan Sports Analytics Conference, but I think he's better by himself or with a group of guys that don't need verification to let his assertions stand in the conversation.
I do think that the Henry Abbott + John Hollinger[1] dynamic was good since Abbott is more of a curious amateur type and willing to withhold judgement until the facts come in. But if Silver is a baseball guy (some of the stuff that Silver's done on basketball isn't very good, I don't think he's really immersed in the sport), then I wouldn't necessarily expect the paths of those two guys to cross much.
[1] Though I have reservations about some of Hollinger's work, especially PER, which is just a linear weights metric with weights apparently chosen to coincide with conventional wisdom on the value of players. There are superior player evaluation metrics, but PER is very marketable to normal fans. Hollinger does seem to know his stuff though, and he's done a great job in Memphis thus far. It's just unfortunate that he got famous for a ho-hum metric.