The players that were perceived to have been let go early in their career:
Lester
Betts
Ellsbury
Everyone else mentioned was let go when their career was on the downturn, even if some had productive seasons left. With Betts, you could see 10 more productive seasons. If Bogey leaves, you could see another 6-7 years. Raffy? Another 10 years if he leaves.
The worry is that there are legit concerns about Bogey and Raffy staying. Letting homegrown players like that walk is a bad look for a "big market" team. The sting is much less if it happens when they are 34.