Pedroia Sad About Lester, Is Boston Sad Too?

The Boston Red Sox lost the Jon Lester sweepstakes to have him sign with the club. Whether they are better off with or without him, let us leave for another time. One all-star player in particular was vocal about his thoughts and emotions regarding Lester’s move to the Chicago Cubs.

Dustin Pedroia, the starting second baseman and American League MVP in 2008, was very emotional about his good friend deciding not to come back to Boston. ESPNBoston’s Joe McDonald reported yesterday that “Pedroia and Lester spoke countless times during Lester’s free-agency period, with the second baseman putting on the full-court press to try to convince the lefty to return to Boston.” Pedroia’s efforts were not irrelevant to Lester, but they did not amount to changing his mind.

“I’m going to miss playing with him and going through the grind with him. When he called me and told me, the things he said were just proof of why he is the best,” said Pedroia (McDonald).

It is the business of sports that players come and go, according to multiple factors besides money. Finances tend to sway many players in a particular direction. Sometimes, it is about loyalty to their friends. Sometimes, it is about loyalty to their families. Lester’s new contract will pay himself and his family between $20 million and $27.5 million each year for the next six seasons, with another $25 million in an option deal in 2021. You cannot blame a man wanting to provide his close-knit family with a guaranteed investment in his services, even if friends are pleading for him to take less money somewhere else.

The question becomes: how much is enough? Many fans would argue that the millions he would have made in Boston would have been more than enough for his family and the family living next to him. Lester could collect on investments and interest, while playing for the team he says that he loved playing for. Will Chicago cheer for him like Red Sox Nation did when he came back from cancer?

There are also many fans and experts who believe that Lester would have had a much better chance of winning with Boston. Others believe he has a great shot pitching on a division champion with the Cubs. Regardless of the truth to any of those notions, his close friend could not convince him of resigning. If he really wanted to play with his friends and was torn about breaking hearts in Boston, we will never know. Even if he did only pick the money, as far as his family is concerned, can we blame him for that?