THe funny thing is, Lackey is remembered as a good signing by a lot of people despite his horrific first two seasons followed by a missed third season. He did bounce back, but it's not like his trade netted that much - Joe Kelly and what was left of Allen Craig. But his bounceback season netted a ring.
Consequently, JD Drew gave the Sox two good seasons on a five year deal, just like Lackey, but was never appreciated at all, despite playing for the same number of title teams. But Drew gt his ring in the first season and then nothing for the next 4.
I guess it's also in the timing.
Julio Lugo also won a ring here, but no one thinks he was a good signing...