You don't let established winning talent walk for draft picks. That's like selling your house for lottery tickets. Also, by letting established talent walk has had the effect of depleting the organization's prospects, because they were forced to trade prospects that are not ML ready for established players. It just makes no sense the way this FO has approached things. They've let established talent leave, traded top prospects to get lesser replacements, and in return they got extra draft picks. Yuk!! It seems like they screwed themselves. If the FO is so good at picking talented prospects they shouldn't need so many extra picks. There aren't that many Hall of Famers and All Stars in each draft If your scouts and FO are not good enough to pick off these rare players with it's own picks, what makes you think they'll do better with a few extra picks.
I have disagreed with the moves that this FO has made since they won the championship. This year the chickens have come home to roost. This team was awful. In many ways it was one of the worst Red Sox teams in decades. I believe the FO has received the cold slap of reality that their approach was doomed to failure. They went into this season in a position where the team could be competitive if every one stayed healthy and everyone had good years. In a situation like that, it only takes a few key injuries or players having off-seasons for things to spiral downward very quickly. If the FO was not embarrassed by a team that was out of it by the second week of August for $120 million, well... they should have been embarrassed.