Cubs: 3 players whose futures with team are doomed after shortened season

Cubs will undoubtedly refuse to pick up Jon Lester’s 2021 option

When it’s all said and done, Jon Lester will go down as arguably the biggest free agent signing in Chicago Cubs history. After all, he came to town and, immediately, the team went from rebuilding to contender – en route to three NLCS, a World Series title and two division crowns.

Lester has won more than 18 games twice with Chicago, earned a pair of All-Star selections, finished runner-up in 2016 NL Cy Young voting and for the last half-decade been a constant in the rotation. But the guy he is today isn’t the one who formed part of the Cubs’ three-headed monster five years ago.

This year, the veteran lefty has battled through some very real struggles, even admitting that he’d lost confidence on the mound at one point. In typical ‘Big Jon’ fashion, he bounced back with a gem in his very next start, but you can no longer expect a quality outing every five days as you might’ve in the not-so-distant past.

With a $25 million vesting option for 2021, it’s a foregone conclusion the two are set to part ways barring a new deal. Given his age and declining stuff, the sad truth is this: it’s time for the Cubs and their beloved left-hander to go their separate ways.