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Chicago Cubs: To sell or not to sell

By David Hill

NEW YORK, NY - AUGUST 29: Jon Lester #34 of the Chicago Cubs in action against the New York Mets during the first inning of a game at Citi Field on August 29, 2019 in New York City. (Photo by Rich Schultz/Getty Images)
NEW YORK, NY - AUGUST 29: Jon Lester #34 of the Chicago Cubs in action against the New York Mets during the first inning of a game at Citi Field on August 29, 2019 in New York City. (Photo by Rich Schultz/Getty Images) /
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The Chicago Cubs have two key pitchers approaching free agency. With a shortened season where anything can happen, this may be the time to sell.

Once the 2020 season ends, the Chicago Cubs are going to have some questions they will need to answer. Jose Quintana is due to be a free agent, and the Cubs hold a $25 million option on Jon Lester with a $10 million buyout. As great as Lester has been, there is virtually no chance that they pick up that option.

The Cubs were also virtually silent this offseason, with their biggest signing being Steven Souza. With Quintana and Lester likely to be free agents after this season, and the majority of the core of their roster slated for free agency after 2021, the Cubs are at a crossroads.

They are also navigating in a difficult situation. With a shortened season that could have as few as 50 games, virtually every team has a chance at the postseason. All they have to do is be hot at the right time. This includes the Cubs, whose talent is undeniable.

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At the same time, it is undeniable that they will not be able to keep everyone together. Lester showed signs of slippage last year, which is to be expected for a 35 year old pitcher. His 4.46 ERA was his worst mark since 2012, and his 1.497 WHiP was his worst since his 15 game stint as a rookie in 2006.

Quintana, likewise, had a down year. The usually dependable starter posted a career worst 4.68 ERA and a 1.386 WHiP, a down season in a year where virtually the entire pitching staff seemed to struggle. But at 31 years old this season, there is reason to hope that he can return to form.

It is certainly possible that both pitchers can find lightning in a bottle over the short season, propelling the Cubs to a playoff push. But with the uncertain future, and plenty of free agents after the next season, it may be time to start the rebuild. That will start with Lester and Quintana, two players that the Cubs should sell to teams looked to make that unexpected push to the postseason.

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The Chicago Cubs will need to decide whether or not it is time to sell. This should not be that difficult of a question as they look forward.

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