Again, it matters on the question. Let's just look at MLB Network for example.
If the question is: How do you best field a groundball and turn the double play? I want Harold Reynolds giving me the answer.
If the question is: Who is more valuable between X and Y player? I want Brian Kenny giving me the answer.
A baseball analyst to me, is going to be answering 10 times as many questions like the second one than the first one. That is why I would much rather have guys like Brian Kenny being analysts than guys like Harold Reynolds.