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Come Fan with UsThursday, June 25, 2026

Say hey, baseball: Jon Lester’s decision has been delayed

Your Friday morning look at the game includes the Dodgers changing Lester’s schedule, Chase Headley’s mystery offer, and what are the Braves even doing?

Listen, we know it’s tough to catch up on everything happening in the baseball world each morning. There are all kinds of stories, rumors, game coverage, and Vines of dudes getting hit in the beans every day, and trying to find all of it while on your way to work or sitting at your desk isn’t easy. It’s okay, though, we’re going to do the heavy lifting for you each morning, and find the things you need to see from within the SB Nation baseball network as well as from elsewhere. Please hold your applause until the end.

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This week has just been full of Jon Lester reveals. First, we got word of the offers that Lester had been receiving: The Cubs led the way at $138 million, with the Red Sox willing to go to at least $130 million. No one knows the Giants’ offer yet, but the most recent discussions said they were “all in” on Lester, so from the sounds of it they’re willing to shell out the same kind of offers we’re all under the impression the Sox and Cubs will. The expectation was that Lester would make a decision among these three teams by the end of this week, before the winter meetings begin, and that familiarity and a level of comfort was going to play into the decision.

Then word of a mystery team arrived, and that team turned out to be the Dodgers. The Dodgers have more money than all three of these teams, and they have plenty of former Red Sox officials working for them, ones Lester is familiar with. He has old teammates in Los Angeles as well, and they’re built to win: suddenly the whole picture has been muddied. Ken Rosenthal reported on Thursday night that Lester’s decision is no longer expected before the meetings, which just makes it sound as if the Dodgers are as legitimate a threat as everyone believed they could be.

If you needed further confirmation that the Dodgers are serious in their pursuit of Lester, the fact they’re discussing sending Matt Kemp to the Padres might just be it. Kemp is still owed $107 million over the next five years, the Dodgers have an outfield logjam, and Lester is going to cost even more than that per year.

If the Dodgers do sign Lester, what are the Red Sox to do then? There are a number of plans to follow-up on, none of them as perfect as just handing Lester large checks for six years, but a few of them should do just fine with the offense Boston has put together.

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