Chicago Cubs: What does the future hold for Jon Lester?

If the Chicago Cubs are to compete in 2020, they’ll need veteran southpaw Jon Lester to return to form – at least to a degree.

It is no secret that left-hander Jon Lester struggled this year, especially at the end of the season when the team needed him most in a bloodbath of a Wild Card race. However, the Chicago Cubs signed Lester to a six-year, $155 million deal in 2014 with the intentions of bringing in one of baseball’s best starters to help the Cubs break a century long World Series drought – so, knowing that box is checked helps, to a degree.

At the time of the signing, Lester was 30 years old. He might not have been considered old at the time, but signing him for six years the Cubs front office knew he could possibly regress with age. Lester turns 36 in January. Yes, he’s come through many times over his several years with the team but the 2019 season has displayed his weaknesses and seeming regression.

More from Cubbies Crib

• Cubs starting pitching has been thriving on the North Side
• Make no mistake: the Cubs are very much about power hitters
• Cubs are giving pitcher Javier Assad a deserved shot
• Cubs: It’s time to start thinking about potential September call-ups
• Cubs: P.J. Higgins deserves to be in the lineup on a daily basis

Though he has been regressing, with age comes experience, and in Lester’s case: three World Series rings. The grizzled hurler has been in the bigs since 2006 and spent from 2006 to 2014 with the Red Sox.

Though he was diagnosed with a rare form of lymphoma, Lester went to the 2007 World Series with the Boston, pitching the final game of the series as the team reigned victorious. He also went to the World Series with the Red Sox again in 2013. In 2014 he had a brief stint with the Oakland Athletics, which ended terribly in the postseason.

Most notably, Lester won the 2016 World Series with the Cubs. He started the first game of the World Series against the Cleveland Indians, where he took a loss after allowing 3 runs across 5 ⅔ innings. In fact, Lester came in clutch in relief in the seventh and final game of the World Series, leading the Cubs to their first World Series title in 108 years.

Since then, though, it’s been a mixed bag, to say the least.

In the 2019 season, Lester pitched the fewest innings since coming to Chicago (171 ⅔), in which he allowed 205 hits and had a 1.497 WHIP. Following a devastating loss to the Oakland Athletics after the All-Star Break, Lester called himself the Cubs’ “weakest link.” In that game on August 6, Lester gave up a career-high 11 runs in the 11-4 loss.

The accomplished postseason standout’s contract runs through the 2020 campaign. His 2021 fate  will be determined via a $25 million team option with a $10 million buyout. If Lester hits the 200-inning mark next season, the option becomes guaranteed. If Lester turns in a repeat of his 2019 showing, that seems pretty unlikely.

Still, we’re all hoping that Lester can get back to his old ways and anchor the rotation – both for his own sake and the short-term future of the Cubs organization.