This seems unfair. One of the funny things fans say is "you can only evaluate a move after waiting to see if it works". But really, that is garbage. The only accurate evaluation of these moves is AT THE TIME YOU MAKE THEM, because all you have are percentages.
You look at the Pierzynski signing at the time Cherington made it, what was he looking at:
- A solid starter who was going to command a multiyear deal
- A couple of near big league ready guys who were not quite there, but both looked like better prospects than the solid starter
- Almost all free agent catching was some variation of meh
What are the choices? Sign a bridge guy or take your shot with the not quite ripe kiddos. I'd have gone with #2, but it was not at all obvious. Cherington's move was one of the two sensible things to do - and it did not work out. Nobody could have expected the AJ signing to be as actively negative as it was.