Top 3 MLB Free Agency Predictions As Winter Meetings Continue

Where will the carousel land by Wednesday?

Sep 14, 2025; Cumberland, Georgia, USA; Houston Astros starting pitcher Framber Valdez (59) pitches against the Atlanta Braves during the first inning at Truist Park. Mandatory Credit: Dale Zanine-Imagn Images | Dale Zanine-Imagn Images

The Major League Baseball Winter Meetings are well underway, and in the first 24 hours or so, we haven't seen much action. It's time to will that action into exsistence.

Based on rumors, active goings-on, and educated hunches, we'll proceed from here to predict three major signings that will take place before the proceedings in Orlando conclude on Wednesday evening.

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Kyle Schwarber returns to Phillies

Oct 8, 2025; Los Angeles, California, USA; Philadelphia Phillies designated hitter Kyle Schwarber (12) leaves the field after the game against the Los Angeles Dodgers during game three of the NLDS round for the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images | Kiyoshi Mio-Imagn Images

The Pittsburgh Pirates reportedly made a four-year offer to Schwarber sometime in recent days, and when free agents are actively talking about dollars and cents, that's often a sign that the sweepstakes are somewhat close to ending. But with all due respect to the Pirates, that report did nothing to move our projection models.

It's always made the most sense that Schwarber would return to Philadelphia. He was already making $20 million per year there, so bringing him back is easier to envision than adding him to another big-market roster like the New York Mets or Boston Red Sox.

And while everyone loves a coming-home moment, the Cincinnati Reds just don't seem to ever get in the mix for true superstars in free agency, as their biggest free-agent deals in franchise history were $64 million apiece for Mike Moustakas and Nick Castellanos.

Orioles make huge splash with Framber Valdez

A previous predictions article on this site had Valdez headed to the Mets, who he reportedly met with last month at the GM meetings, alongside the Baltimore Orioles and San Francisco Giants. But given Tuesday's word from Will Sammon of The Athletic that New York is once again hesitant to do a long-term deal for a starting pitcher this winter, we're going to pivot.

This offseason is Baltimore's chance to make a splash under owner David Rubenstein, whose goodwill from the fan base will quickly evaporate if the payroll doesn't jump up. And the Orioles' need for quality innings is so dire that Valdez truly looks like the perfect fit, even if he might start to show signs of aging in the next few seasons or so.

Cubs seal deal with Zac Gallen

Sep 26, 2025; San Diego, California, USA; Arizona Diamondbacks starting pitcher Zac Gallen (23) throws a pitch during the first inning against the San Diego Padres at Petco Park. Mandatory Credit: David Frerker-Imagn Images | David Frerker-Imagn Images

It's always good fodder for MLB social media when an insider goofs and reports something prematurely, and that's what happened on Saturday, when Bob Nightengale of USA Today reported that a deal was imminent between Zac Gallen and the Chicago Cubs, only to immediately backtrack and write that the Cubs were "hopeful" of signing the 2023 All-Star.

If Gallen goes elsewhere and balls out, the Cubs will have to endure jokes about the time they had him signed for five minutes for the rest of eternity. But Chicago has also shown the clearest interest in the 30-year-old, and their rotation is way too left-handed at the moment. Why shouldn't the longtime Arizona Diamondbacks star end up in Wrigleyville?

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