To me it doesn't matter if its Boston, NY or Tampa. Going to Boston gives him a pretty legit shot at something he DOES NOT have. That is a ring. Apparently flying under the radar in SD on a losing club and being close to family outweighs the chance to get a ring.
. . . and implicit in this formulation is the idea that there is something morally wrong with him for choosing to stay in SD ("flying under the radar" implies cowardice; "on a losing club" implies that he doesn't want to WIN!!!111!1).
This is ridiculous. Let me show you how easy it is to flip this on its head.
Carl Crawford signed a long-term deal a couple of years ago. Had he not, '08 would have been his first year eligible for free agency, if I'm counting correctly.
The Rays are contenders this year. Let's say they make the playoffs. As the champagne sprays around the locker room, and Crawford gets pulled in front of the camera cryiing, I GUARANTEE (GUARANTEE!!!!!) you that the announcer will intone solemnly about how "Carl Crawford could have left this losing franchise as a free agent. . . . but Carl wanted to stay here. . . he liked the town, liked the club. . . felt like they were putting something important together. . . could have played out his six years and gone to New York or Boston for the big bucks. . . but wanted to be a key guy here. . . wanted to be a cornerstone that they could build around. . . nice to see a guy who cares about loyalty in this mercenary age. . . "
I'll bet $500 to your $5 that this happens, and it will be the easiest $5 I ever made.
But now Giles is somehow deficient in character because he wants to stay in SD.
Players have their reasons. They are legitimate. We are unlikely to know them.
Any formulation along the lines of: "our team is so fantastic that the player ought to be honored to come here, and that he is obviously a moral weakling if he doesn't have the good sense to humble himself and appreciate that" is utter crap.