The Winter Meetings are officially underway, and for the New York Yankees, the stakes couldn’t be higher. Insiders report that General Manager Brian Cashman is actively engaged in negotiations across multiple positions, aware that the next 96 hours could define the Yankees’ 2026 season.
The current focus is split between three primary needs: a premier power bat, an elite late-inning reliever, and rotation depth following early-season injury concerns for key starters.
🔥 Top Free Agent Targets: The Power Trio
The Yankees are reportedly in the thick of discussions for three high-profile free agents, all of whom are represented by Scott Boras (known to finalize deals at the Winter Meetings).
| Position | Player | Rumored Contract / Role | Urgency |
| Outfield | Cody Bellinger | Reunion is likely. Projected 6 years, $\sim$150-200M. Offers a much-needed left-handed bat and Gold Glove defense across four positions. | Extremely High. He is viewed as the top priority to replace his own production and balance the too left-handed lineup. |
| First Base | Pete Alonso | Projected 3-5 years, $\sim\$30M$ AAV. The top 1B on the market. Prying him from the Mets would be a massive coup and provide a powerful right-handed bat to protect Aaron Judge. | High. Provides a definitive answer at 1B amidst concerns over Ben Rice’s readiness. |
| Bullpen | Edwin Diaz | Projected 3-5 years, $\sim\$25M$ AAV. Targets him as the elite late-inning relief replacement after Devin Williams signed with the Mets. | High. Essential to maintain the Yankees’ tradition of a dominant bullpen. |
🔄 Trade Talks: Prospects on the Block
With the Yankees’ outfield currently crowded and their pitching depth strained by injuries to Gerrit Cole and Carlos Rodón, trade speculation is focusing on moving high-value prospects for immediate needs.
- The Prime Trade Chip: Spencer Jones (No. 4 Prospect) is widely named as the most likely centerpiece in a blockbuster deal. Coming off a 35-homer minor league season, his high prospect value could net the Yankees a frontline starter or an established veteran.
- Targeted Assets:
- Starting Pitching: The Yankees need a reliable arm to cover for early-season absences. Trade targets include MacKenzie Gore (Nationals) or potentially Freddy Peralta (Brewers), with the latter only possible if Milwaukee “cracks the door open” on trade discussions.
- Bullpen Depth: Relievers like Pete Fairbanks (Rays) are on the radar to fill middle-inning roles, a need that may be addressed by trading mid-tier pitching prospects like Carlos Lagrange.
🧐 The Biggest Risk: The Outfield Bottleneck
The decision to retain Trent Grisham after he accepted the Qualifying Offer ($\sim\$22M$) creates an immediate logjam, especially if the Yankees re-sign Cody Bellinger.
| Player | Position | Handedness | Problem |
| Aaron Judge | RF | R | Untouchable |
| Trent Grisham | CF | L | Just accepted QO |
| Jasson Dominguez | OF | S (low OPS vs. RHP) | Value is low after a disappointing 2025 |
| Spencer Jones | OF | L | Prospect trade chip |
| Cody Bellinger | OF/1B | L | Top FA target |
The Yankees are currently too left-handed, which increases the pressure to trade one of the young left-handed outfielders (Jones or Dominguez) for a power bat who hits right-handed, or a frontline starter.
