Winter Meetings: Schwarber's Future, Alonso's Free Agency, and the MLB Draft Lottery (2026)

The Opener: Schwarber, Alonso, Draft Lottery

Three storylines to watch as the Winter Meetings roll on in Orlando…

  1. The Schwarber Watch Goes On
    Most expect Kyle Schwarber to re-sign with the Phillies eventually, but the veteran slugger’s market remains robust, drawing interest from around the league. The Mets have joined the list of suitors, joining the Phillies and other clubs such as the Giants, Orioles, Red Sox, Pirates (who’ve extended a four-year offer), and the Reds (Schwarber’s hometown club). Prominent insiders like ESPN’s Buster Olney, MLB.com’s Mark Feinsand, and other pundits have floated the idea that Schwarber could be the first major-position player free agent to lock in his destination. If Schwarber makes a decision during the Winter Meetings, it could unlock a cascade of moves for other players elsewhere.

  2. A Heat Check in Orlando
    Pete Alonso plans to be there in person, traveling from the Tampa area to meet with potential teams face to face. While the Mets aren’t expected to reconfirm interest with their longtime slugger, the Orioles and Red Sox are anticipated to sit down with Alonso to discuss a possible contract. With the overlap among several suitors, Alonso could be a prime beneficiary if Schwarber signs early, since many teams seeking power hitting would naturally eye Alonso as a key source of thump in the lineup.

  3. The Draft Lottery Arrives
    The fourth MLB Draft Lottery is scheduled for today at 4:30 PM Central Time, with 15 non-playoff clubs in the running for a top-six choice in the 2026 draft. The Rockies (who just beat the odds with previous lottery wins) aren’t eligible this year due to two prior lottery wins, and the Nationals and Angels aren’t eligible because of revenue-sharing constraints tied to consecutive lottery eligibility.

With those rules in mind, the White Sox hold the best odds at 27.73% to claim the first overall pick. Yet history shows the top odds don’t always translate into the top pick; remember that the Pirates’ 2022 top-spot win led to Paul Skenes’ selection in 2023, and the Guardians’ surprise 2023 win came from a modest two-percent chance. Beyond the 1-1 pick, the lottery has sparked numerous top-six shakeups, leaving teams with winning records—the Astros, Mets, or Royals, among others—still flirting with an elevated first-round outcome.

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Winter Meetings: Schwarber's Future, Alonso's Free Agency, and the MLB Draft Lottery (2026)

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