Theo Epstein will have his hands full going into presumably his last season with the Chicago Cubs. He will finally be facing many key decisions to shake up the core he created over the last nine years. One of these tough choices being whether to retain Jon Lester or let the former ace choose between retirement or seeking employment elsewhere in free agency.

The left-hander is heading into his age-37 season, and just completed the final year of a 6-year, $155 million deal; in which he produced a 77-44 record, 3.64 ERA, and a World Series ring. He was the first major signing of the current Cubs era and is by many accounts the most successful signing in franchise history. Despite the overwhelming success of his tenure, his fate now lies in the hands of the Cubs front office. If it was up to Lester himself he would be back in the rotation next year, but it remains to be seen if he will get his wishes.

The Fit

The Cubs pitching staff will be short on arms again in 2021:

This season, the Cubs relied on the unexpected success of Alex Mills and the spot starts from Adbert Alzolay to get through the regular season. Oft-frustrating members of the rotation, Tyler Chatwood, and Jose Quintana spent more than half of the season on the IL and now head into free agency. It is highly unlikely either will be seen wearing a Cubs uniform again. Only Kyle Hendricks, Yu Darvish, and Mills are returning under contract as part of a depleted rotation.

Lester provides the franchise the opportunity to roll out a 5th starter with obvious familiarity and success. Allowing him one more year on the bump gives the organization more time to get comfortable with the development of Alzolay and highly toughed prospect Brailyn Marquez before slotting them into the rotation full time. Lester would also provide a solid option out of the bullpen later in the season if need be. Going into a potential playoff series with a guy who is number 8 all-time in postseason innings is never a bad situation.

Financial Situation:

The Cubs can pay Lester $25 million to be on the roster or send him to free agency with a $10 million buyout, they will almost certainly go with the latter. However, this does not guarantee that Lester will not be in a Cubs uniform again. Given the assured financial security, it is not crazy to assume Theo and Lester work something out to retain him on a 1-year free-agent deal. Top available hurlers like Trevor Bauer and Marcus Stroman will certainly require much larger contracts outside of the value the Cubs will be willing to spend in free agency. By offering a few million for his services, the Cubs would fill a need with an in-house option and Lester would still command a total payday well over league average.

Last Go-Around:

Performance and financial-based arguments aside, if a re-signing happens this may ultimately be why: The Chicago Cubs organization is at a turning point. Players who once looked to have jerseys hanging from the flagpoles at Wrigley will be suiting up for other teams. Theo Epstein will also likely be holding post elsewhere in the MLB after next season. Epstein drafted Lester and later convinced him to come to Chicago, in turn jumpstarting the end of the Cubs rebuild. Going from last place to starting a run consisting of three straight NLCS appearances and a World Series victory. Without Lester, it is hard to imagine what the turnaround of Cubs baseball may have looked like.

Free Agency Reunion Seems Likely

There is no question that Jon Lester has lost a step since his first years on the North Side. However, he still shows up in big-game situations and his statistical decline has not been drastic. His hard work and fun attitude have embodied everything the Cubs window of championship competition has stood for. It seems only right to reward him a proper send off to end his illustrious career. After all, a shortened season with no fans in the stands is no way to say goodbye to one of the most important players to ever don Cubs’ pinstripes. Given his relationship with Theo Epstein and longtime catcher turned Manager, David Ross, it only makes sense to expect Lester back in some form for a final time in 2021.