Chicago Cubs: Breaking down a starting rotation full of Cy Young contenders

Fulfilling his promise, Lester leads Cubs to a title

When the Cubs made their free agent pitch to Jon Lester, they put together a presentation centered around him being the guy to break the curse.

Little did they know, two years later, that situation played out perfectly. Lester stepped up, winning 19 games over the course of the regular season, taking the ball time and time again on baseball’s biggest stage in October.

And, after a second-place Cy Young finish, the southpaw is ready to do it all again in 2017.

"“The championships and the World Series — that’s stuff you can’t predict,” he told CSN Chicago. “It’s stuff you strive to do every single year. So that’s all we’re going to focus on again. Our team goal again is to win a World Series.”"

$155 million is a lot of money – no matter how you slice it. But since he joined the Cubs, Lester has been a true ace. In two years, he’s won 30 games, pitching to a 2.84 earned run average and 1.070 WHIP.

Both seasons, he broke the 200-inning benchmark. Last year, he earned the fourth All-Star selection of his big league career. Along with teammate David Ross, he led a Cubs team to heights we’d only imagined prior to last season.

Now, Ross is retired – taking up residence on Dancing with the Stars. Lester is paired with backstop Willson Contreras, marking the first time he’s pitched without Ross regularly since he joined the Cubs.

Some things have changed, there’s no doubt. But don’t expect anything but the best from Lester: it’s all he knows.