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Reading: Could the 2025 MLB Winter Meetings Deadline Accelerate the Free Agency Frenzy?
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Sports Daily > Baseball > Could the 2025 MLB Winter Meetings Deadline Accelerate the Free Agency Frenzy?
2025 MLB Winter Meetings: Will the deadline help speed up free agency?
Baseball

Could the 2025 MLB Winter Meetings Deadline Accelerate the Free Agency Frenzy?

December 12, 2025 10 Min Read
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Orlando, Florida — The trade market is busy, but many of the top free agents this year have yet to receive offers or sign deals.

Major League Baseball’s annual Winter Meetings gather executives, agents, and managers, with plenty to observe. Here’s an update on what’s happening behind the scenes.

Market Movement is Slow

The Winter Meetings wrap up Wednesday in Orlando, but there hasn’t been significant activity since Kyle Schwarber re-signed with the Phillies, and Edwin Diaz agreed to a modest three-year contract with the . Industry insiders believe Schwarber’s five-year deal may reignite the market for position players, but changes will take time.

Yankees GM Brian Cashman voiced frustration Wednesday morning about the “glacial speed” of free agency and trades this offseason. As MLB’s longest-tenured baseball operations head since 1998, Cashman even suggested discussing postseason contract and trade deadlines to force decisions and improve the stagnant situation.

That said, many private talks remain ongoing without finalized deals. Mets Director of Baseball Operations David Stearns noted that the trade market is usually active across all positions. He feels teams may be more open to creative deal structures this offseason than in recent years.

The next collective bargaining agreement will likely introduce an offseason trade deadline, but patience is necessary for now. — Tozar

Schwarber’s Return Could Energize a Slow Market

While top players at key spots remain unsigned, many believe the Phillies signing Kyle Schwarber might kickstart more activity in free agency and trades.

Agent Scott Boras compared the free agent market to the weather: “One event can trigger four or five others.”

Boras hopes his clients’ teams won’t just settle for playoff contention but spend enough to compete with powerhouses like the , who strengthened their roster by adding Edwin Diaz. Although Boras doesn’t represent Schwarber, the 33-year-old designated hitter’s $150 million, five-year deal will benefit Boras’ clients in their early 30s.

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“Powerful premium talent is in high demand, and teams are willing to give longer contracts,” Boras said. Young players deserve the long-term deals now seen in the market.”

Boras represents Alex Bregman, Pete Alonso, and Cody Bellinger — all top position players still available along with Kyle Tucker and Bo Bichette. These players signed shorter, opt-out-heavy contracts in past offseasons, hoping current conditions lead to longer-term offers. Bellinger turns 30 this season; Alonso just turned 31; Bregman turns 32 in March.

Some expected more trade activity than free agent signings this week, but free agency has been slower than anticipated.

president of baseball operations Andrew Friedman acknowledged it’s tough to get momentum before more free agents sign. The market’s large supply may be slowing things down. — Kavner

Boras Brings Wit to Bellinger’s Market Prospects

MLB super agent Scott Boras entertained with puns at the Winter Meetings, joking about players like Zac Gallen, Ranger Suarez, Tatsuya Imai, and Alex Bregman.

For example:

  • “Galen is always in demand when it comes to pitching.”
  • “Add Suarez in the postseason, and you’ve got a ‘Ranger’ full of weapons.”
  • “At 27, Imai’s velocity makes him a dream player.”
  • “Bregman’s consistent postseason performances are like a trip to Wonderland.”

Boras also commented on Tigers pitcher Tarik Skubal, who might be traded: “Skubal is a SABR-resistant asset. Without him, the Tigers operate like a mystery machine.”

Within the humor, Boras shared insights on Cody Bellinger’s market: “Great players don’t shy away when pulled from the lineup. A versatile outfielder who can cover all parts of the field is rare. Expect teams flocking to sign him.”

If guessing his destination, teams like the Yankees, Reds, Mets, , Phillies, Giants, Blue Jays, or Angels could be contenders. — Kavner

Padres Favor Mason Miller as Reliever

The Padres plan to keep star reliever Mason Miller in the bullpen rather than move him to the starting rotation, along with relievers Adrian Morejon and David Morgan.

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Manager Craig Stammen cautioned that changing a player’s role is risky for health and performance. With Robert Suarez possibly leaving in free agency, Miller would become the primary closer. The Padres led MLB in bullpen ERA and WHIP last year, with Miller posting the highest strikeout rate among qualified relievers.

“It’s best to use them strategically in the bullpen,” said Stammen. — Kavner

Pete Alonso’s Winter Meetings Plans

Free agent first baseman Pete Alonso is driving from Tampa to Orlando to meet teams in person this week. Mets exec David Stearns confirmed Alonso knows the Mets well, but he will explore other opportunities while staying in touch with New York.

Re-signing Alonso remains a priority for the Mets, but the team appears more measured than before. Last year Alonso expressed some disconnect with the Mets over his role. Stearns respects Alonso’s right to explore the market.

Alonso wants a long-term deal beyond four years. Meeting teams face-to-face gives them a chance to better understand his character and drive, which may improve his market compared to last year when he clung to a qualifying offer. — Tozar

Brian Cashman on Yankees’ Plans

Cashman hinted the Yankees don’t have extensive roster needs this offseason, focusing mainly on re-signing free agent outfielder Cody Bellinger, though the team is aware of its lineup’s left-handed imbalance.

Bellinger’s strong performance against left-handed pitching and his reverse splits are appealing. The Yankees also need to bolster their bullpen.

Cashman dismissed claims the Yankees must keep payroll under $300 million despite owner Steinbrenner’s hopes for cuts. To improve, they may lean more on trades than free agency. — Tozar

Trade Discussions Gain Momentum

Unlike last year’s blockbuster signing of Juan Soto, this year has seen no major early moves. Teams are turning to trades to find impactful players since many top talents avoided the deadline.

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Notable recent trades include Sonny Gray to the Red Sox and deals involving Marcus Semien, Brandon Nimmo, Taylor Ward, and Grayson Rodriguez. Upcoming names to watch are Nationals’ Mackenzie Gore and CJ Abrams, Diamondbacks’ Ketel Marte, and Marlins’ Sandy Alcantara and Edward Cabrera.

A key question is whether the Tigers will trade Tarik Skubal in his final contractual year. The decision likely hinges on developments before the deadline and any attractive offers. — Kavner

Top-Free Agent Market Quiet

Only three major free agent deals were completed by Monday: Dylan Cease to Blue Jays, Devin Williams to Mets, and Josh Naylor back to Mariners. Most top free agents remain unsigned.

Kyle Schwarber’s multi-year offer from the Phillies outmatches interest from the Pirates and Reds. Given his impact at the plate and leadership, Philadelphia remains the favorite suitor. His signing might energize the stalled market.

As Schwarber enters his age-33 season fresh off a career year, a DH role would enhance many lineups, potentially boosting free agency activity. — Kavner

Team Standings Before the Winter Meetings

Top All-Stars like Kyle Tucker, Alex Bregman, Kyle Schwarber, Bo Bichette, Pete Alonso, and Cody Bellinger are making decisions. As offseason rosters evolve, here’s where all 30 teams stand currently. — Kavner

10 Biggest Stories from the Winter Meetings

Labor tensions, the ’ quest for a three-peat, and the next influx of Japanese stars are among the major topics shaping the MLB offseason and likely trade/free agency dynamics. Here are the 10 biggest stories from the conference. — Tozar/Kavner


Fan Take: This latest Winter Meetings buzz highlights the delicate balance of patience and urgency in baseball’s offseason. Fans should watch closely, as key signings like Schwarber’s and moves in the trade market could reshape team dynamics and playoff hopes across the league.

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