How Much do Players Worry about Legacies?

It crosses my mind every time I see Carlton Fisk throw a first pitch to Luis Tiant. It happened again as i wanted Jon Lester sit there in his Cubs uniform doing his best to prove that he didn't lie to the fans.

How much do players care about the legacies they leave in a town when their playing days are over?

I thought of it with Johnny Damon. Sure, he went to the highest bidder. I can't really fault him for that. But, he was really looking for his last contract. He ended up hanging on for a few more years after that, but it was basically his last chance to be a contributor. He could have stayed in Boston, as a curse-busting idiot. He would be adored. He would be a legend. For the rest of his life he could make personal appearances. He could be given ovations when he showed up at Celtics games. He would have a life of adoration. Instead, he chose to go to NY and be yet another Yankee who never quite "earned his pinstripes." He became a hired gun playing second (or third, or fourth) fiddle to Derek Jeter. Now, he may go back to the stadium for a round of applause. And, he;s been at Fenway once or twice since then. But, his legacy would be twice what it is now in Boston compared to what it is combined in all the other cities he's played in combined.

Did he think about that?

It looked like Lester did. After all, he mentioned the prospect of finally winning a Cubs championship. He knows that if he does that, he can have free drinks in Chicago for the rest of his life (provided, I suppose, he doesn't go all Curt Schilling on them). But, what if he doesn't win? He'd just be another guy that came to the Cubs and left without a ring. Does that get you called back to Wrigley? Does that get you a free beer? Probably not. A six or seven year stint on mediocrity does nothing.

So, he needs to leave the door open just a bit in Boston. Like Fisk somehow did, and Roger Clemens wished he did, and is trying to do. After all, if he plays his cards right, Boston could be a nice little fallback legacy for him. A place to go sit in the "Legends Box" and wave to the adoring crowd. He could do that forever as a two-time champion, who just happened to have played somewhere else as well. After all, I think Fred Lynn is in that box at least once a homestand.

I wonder how much Lester thinks of that whenever someone asks him about Boston. Does he think to himself, "I may still need these guys."? "I may want a chicken stand out on Yawkey Way some day, if I can't get one on Addison."

Does the fallback plan bring comfort?