Jon Lester, with his old uniform number monogrammed on his shirt sleeves and metal deer as cuff links, became the first free agent to sign with a team because of its history as a lovable loser. If the Chicago Cubs had won a World Series in the past couple of years or even in our lifetime, Lester likely would not have been signing his six-year, $155 million deal as the richest player in franchise history.

More…