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Come Fan with UsWednesday, June 24, 2026

Say hey, baseball: Jon Lester runs the winter meetings

Monday morning’s baseball includes Jon Lester holding up the pitching market, Chase Headley’s negotiations, and the beginning of the winter meetings.

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.

★★★

It was a quiet weekend for baseball, as the whole game tends to shut down in anticipation of the winter meetings. Things are about to ramp right back up, though, as those meetings begin Monday, which is presumably the day you are reading this on. Almost everything you care about at the meetings begins with Jon Lester, even if your team is not involved in the negotiations for the free agent market’s top left-hander at all. Buster Olney reported the pitching market is waiting for Lester to sign, and the moment he does, things are going to move fast. Offers for James Shields should start to come through from the teams who didn’t get Lester, Max Scherzer will know what price he’s trying to top, and all of those No. 2-caliber starters sitting on the trade market will start to be moved.

Just who is going to get Lester remains up in the air. As we discussed in this space last week, the unveiling of the Dodgers as the mystery team delayed Lester’s decision, which was supposed to come before the meetings: that insinuates they’re a serious competitor for his services. Red Sox owner John Henry flew down to Lester’s Atlanta home to meet with him in person this weekend before the meetings. The Giants met with Lester’s agents Sunday night to try to get ahead of the game -- this says Monday, not Sunday, but as it’s Monday morning when this is being written, that’s obviously not possible. Also Bob corrected his mistake in the next tweet.

The Yankees aren’t officially involved in the bidding for either of Lester or Scherzer just yet, but it’s worth wondering if they should be, and, if so, which of the two makes more sense in pinstripes.

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