CHICAGO, IL — The veil of secrecy has been abruptly lifted from the Winter Meetings: multiple insiders are confirming that a private meeting between the Chicago Cubs and three-time All-Star third baseman Alex Bregman took place early Monday morning at the Cubs’ training complex.
The meeting, which an anonymous source described as attended by “so many executives at once,” immediately raised suspicions that the Cubs are preparing to “surprise the market” with a shocking short-term but ambitious deal for the free agent.
The Dynamics of the “Short-Term” Shock
Bregman, who opted out of the final two years ($80 million total) of his three-year deal with the Red Sox after the 2025 season, is generally projected to seek a five-to-six-year contract in the $160 million to $180 million range. Th1e Cubs’ rumored “short-term” approach, however, has two highly compelling strategic advantages:
1. Maximizing AAV and Opt-Outs (The Player’s Advantage)
A short-term deal (perhaps 3 or 4 years) would allow Bregman to secure an extremely high Average Annual Value (AAV)—potentially over $40 million—while also including an opt-out after the first or second season.
- Financial Flexibility: This structure gives the Cubs the power of Bregman’s bat and glove for their current contention window without locking them into his age 36+ seasons.
- The Next Big Deal: For Bregman (who is 31 and battled a quad injury in 2025), a short, massive-AAV deal is a chance to prove his health and then hit the market again in his mid-30s, potentially chasing a final, lucrative contract if he maintains his elite performance.
2. Filling the Kyle Tucker Void (The Cubs’ Urgency)
The secret meeting’s urgency is directly tied to the Cubs losing Kyle Tucker, their top offseason target. Bregman, a Gold Glove defender with an .821 OPS in 2025, represents a proven, high-impact bat that stabilizes a critical position.2
| Player | 2025 Games | AVG | HR | RBI | OPS | Value to Cubs |
| Alex Bregman (Target) | 114 | .273 | 18 | 62 | .821 | Elite Defense, Proven Power |
| Cubs Team 3B (Internal) | 162 | .249 | Varies | Varies | ~.750 | Major offensive instability |
By pursuing Bregman aggressively and potentially surprising the market with an unprecedented short-term AAV, the Cubs are signaling a ruthless commitment to contention and a rejection of a slow, multi-year rebuild. The question now is not if the Cubs want him, but if their ambitious short-term proposal is enough to lure him away from long-term suitors like the Red Sox and Tigers.
