Cubs, Jon Lester face uncertainty in terms of his vesting option for 2021

The Cubs and Jon Lester are waiting to see what his vesting option looks like.

Prior to COVID-19 leading to the suspension of the 2020 MLB season, generally Cubs fans knew this might be the last go-round for southpaw Jon Lester. This marks the final guaranteed year of the six-year, $155 million deal he inked prior to the 2015 campaign.

That’s not to say Chicago will cut ties with Lester. His deal carries a $25 million vesting option for 2021 – one that would become guaranteed had he surpassed 200 innings pitched this year in a typical 162 game season. Now that there will be just 60 games played, there’s a great deal of uncertainty for guys like Lester who could potentially be missing out on huge sums of money.

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If that option doesn’t vest, the Cubs have a $10 million buyout on Lester. In other words, an organization that is seemingly strapped for cash, particularly in the baseball operations realm, could get some much-needed financial relief.

According to Ken Rosenthal of The Athletic (subscription required), the league and the MLBPA are working toward a deal on vesting options and retention bonuses. Now, you might just say – look, if Lester needed 200 innings pitched in a normal calendar, then since we’re only playing 37 percent of that schedule, he should only need to hit 74 innings for it to vest.

But then – what is that option worth? It’s hard to envision owners being OK with the idea that they have to pay a player a full option value in 2021 when they didn’t hit the original parameters on the field in 2020. Undoubtedly, these options will look different than originally anticipated – but it’s worth wondering whether or not someone whose option is inherently tied to time on the field will be handled differently this year.

There are several other prominent players in similar situations, but let’s keep the focus on Lester. Assuming the Cubs stick with a traditional five-man starting rotation, each guy would make roughly a dozen starts – barring injury or illness. For someone like Lester, the latter is a very real threat in the wake of COVID-19 and its far-reaching effects on those who have compromised immune systems.

But assuming he’s healthy and makes his 12 starts – the lefty would need to average approximately 6 1/3 innings every time he takes the ball. Is that a feasible number for the 36-year-old hurler? Potentially – but it’s certainly no guarantee.

Last year, Lester averaged just under 5 2/3 innings per start. The year prior? Same story. In fact, the three-time World Series champion hasn’t averaged 6 1/3 innings per start since back in 2016, when he finished as the NL Cy Young runner-up after racking up 202 2/3 innings of work across 32 starts.

And if the Cubs were to decide to go with a six-man rotation? Forget it. It becomes a virtual certainty Lester’s option wouldn’t vest and the two sides could go their separate ways next offseason. This is all hypothetical, of course, until the league and player’s union agree to a framework on this matter – but it could have far-reaching implications for Lester and the team.