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Come Fan with UsSaturday, June 20, 2026

Jon Lester down to Red Sox, Cubs as entire baseball world awaits decision

People in the industry believe that the lefty will receive a deal in the $155-160 million range.

SAN DIEGO -- The entire baseball world is awaiting Jon Lester's decision, and we know this much: the left-hander is deciding between the Chicago Cubs and the Boston Red Sox and is expected to make an official choice in the near future.

Rival agents and executives expressed belief throughout Tuesday that Lester would ultimately end up with the Cubs, and noted that his final deal is expected to fall in the $155-$160 million range. Though Lester has reportedly been pushing for seven years and teams appear willing to only offer six, some speculate that the sides could compromise with a six-year deal that includes either a team or vesting option for a seventh season.

As others have reported, the San Francisco Giants and Los Angeles Dodgers are out of the running for Lester, leaving two of the southpaw's old bosses, Theo Epstein and Ben Cherington, competing for the most talked-about free agent starter in recent history. As Giants' assistant general manager Bobby Evans noted earlier today, Lester's "heartstrings" are believed to play a major role in the decision, which could point to him giving the Sox a final chance to pitch themselves.

I spoke to Cubs’ manager Joe Maddon a short time ago, and he told me that there was “no word yet” on where Lester was going to end up, saying that he would know when he “saw the white smoke.” A couple of Cubs front office members echoed the same sentiments, despite a growing belief within the Manchester Grand Hyatt hotel that the Cubs were the favorite.

Lester's decision could carry over to tomorrow, handicapping a starting pitching market that is set to explode once the white smoke rises from the St. Jon's basilica. Available starters like James Shields, Brandon McCarthy, Ervin Santana and Justin Masterson are expected to gauge their markets based on where Lester ends up.

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