I don't think there's much evidence to support the idea that playing experience is a plus in a CBO.
If you run through the list of the most successful CBOs in history, I don't think you'll find very many former players.
I am suffering from confirmation bias these days, I will freely admit that.
When it comes to Breslow's hiring, the thing that stands out is that the Red Sox ended up with a much smaller field of candidates than they expected, which was concerning and frankly embarrassing in itself. Then they choose a guy who is a total unknown quantity as a CBO, just as the previous guy was. Then they tell us full throttle and follow it up with a stunningly inactive offseason. It's hard to get a sense they have any clue what they're doing any more.