Cubs’ Inexplicable Failure to Engage Jon Lester Leaves Sour Taste

Most Important Free Agent in Club History Deserved Better

Less than $5 million. That’s all the Cubs would have needed to pay to keep the best free agent signing in team history. A man who, for some inexplicable reason given the current state of affairs, made it publicly known he wanted to end his exemplary career on the north side of Chicago. A man whose signing was symbolic of a cultural overhaul within the organization and was, in (very) large part, responsible for the Cubs’ first World Series title in 108 years.

He reportedly approached the team earlier in the winter with an offer lower than the $5 million guarantee he eventually got from the Nationals. Even for a team reeling from the lack of fans and a crippling debt load, that’s like thawing out a small ice cube for liquidity.

Yes, I understand this is a business at the end of the day and that such decisions shouldn’t be made based on emotions or sentimentality. But every now and then, you make exceptions for the sake of loyalty or public perception, a concept that seems foreign to the team’s current ownership. If Lester’s return didn’t call for one of those exceptions, I don’t know what does.



Remember that coveted “free agent destination” label the Cubs have worn proudly since 2015? That’s now gone in the blink of an eye. Why would any star in their right mind want to play for this organization right now, knowing they’d be treated with all the warmth of a TD Ameritrade transaction?

If it’s not a matter of loyalty to players, or lack thereof, it means ownership simply doesn’t care about its fans. That might not be the best way to do business moving forward. David Kaplan of NBC Sports Chicago tweeted that the Ricketts family is $1 billion in debt due to neighborhood acquisitions and construction/renovation projects.

While the Cubs need fans to alleviate that debt, it feels more and more like the green in the wallets of Cubs faithful is more of a target than the Cubbie blue of their hearts. To that end, here are some numbers every Cubs fan should know:

The fact of the matter is that every team in the league suffered losses in 2020 and, in all likelihood, they will do so once again in 2021. Even so, no other large-market organization has mandated payroll cuts like what we’re seeing the Cubs make.

Willson Contreras, a top-5 catcher who’s still in his 20’s and just agreed to a $6.65 million salary to avoid arbitration, could be out the door as a valuable trade piece. Kris Bryant makes almost three times that and has been the subject of seemingly-endless trade rumors for years, so the writing is on the wall for his exit as well. If you think the team is done cutting payroll after trading away Yu Darvish for peanuts and letting Kyle Schwarber walk, buckle up because they’re just getting started.

Whether or not you choose to view all of these decisions as part of baseball’s cold-blooded business, it still doesn’t forgive the way the Cubs treated Lester. He should have been given the chance to retire a Cub, or at least gotten more than a half-hearted effort to retain his services once his deal with the Nats was all but done. Lester was a huge part of what made the Cubs respectable, yet the team would like you to think they literally couldn’t afford to repay the favor six years later.

Not even $5 million. That’s it. If you’re that strapped for cash, maybe it really is time to sell the team.

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