The Jon Lester megadeal remains a dividing line in franchise history, separating the Lovable Losers of before — Billy Goat, Black Cat, “Oh no!” and “We stinks” — from the $3 billion machine the Cubs would become after his decision to sign with a last-place team.
When Lester put on a No. 34 jersey at Spiaggia for his welcome-to-Chicago news conference, the Cubs had won just one playoff round since the 1908 World Series, and that only set up the heartbreak in 2003. After coming up with the Red Sox, Lester wanted to be in a city with a rich sports history that could approximate the atmosphere at Fenway Park. Lester values his comfort zone, and he found that with the Cubs executives he already knew from their time together in Boston.
Now in the final days of that contract, Lester can’t believe how six years went by so fast. As a cancer survivor and a borderline Hall of Famer, Lester could have elected to sit out this…
