The revelation that the Chicago Cubs offered Alex Bregman a lucrative four-year, $130 million contract last offseason—the highest value ever presented by the franchise—only for him to accept a shorter, three-year, $120 million deal with the Boston Red Sox, highlights Bregman’s calculated gamble to maximize his long-term value.
Now that Bregman has officially opted out of his Red Sox contract after just one season (a near certainty, according to sources), the Cubs are once again at the center of the “Bregman Sweepstakes.”
Why Bregman Rejected the Cubs’ Offer
The reason Bregman turned down the Cubs’ four-year deal in favor of a shorter commitment with a similar guarantee was primarily due to the Annual Average Value (AAV) and contract flexibility.
- Higher AAV: The Red Sox deal provided an AAV of $40 million per season ($120M / 3 years), which was significantly higher than the Cubs’ offer of $32.5 million per season ($130M / 4 years). Bregman took the higher short-term salary.
- Opt-Out Flexibility: Crucially, the Red Sox deal included an opt-out clause after the first year (2025), giving him immediate flexibility. The Cubs’ reported offer was for four years, but sources indicate the first opt-out was after the 2026 season, locking him in for two years.
- Betting on Himself: By taking the short deal with the immediate opt-out, Bregman bet on having a strong 2025 season to re-enter free agency without a qualifying offer attached, securing the long-term, high-value contract he originally desired. His 2025 performance (.273 AVG, .822 OPS, 18 HR in 114 games, 3.5 WAR) was strong enough despite a quad injury and a rough finish to prove his market value.
Cubs’ Strategy: Pivot from Tucker to Bregman
The Cubs’ initial pursuit of Bregman and their renewed interest confirm President Jed Hoyer’s strategy to bolster the offense, especially with Kyle Tucker expected to command a historic contract of around 11 years, $418 million.
- Tucker’s Price: Tucker’s projected price tag (the fifth-largest predicted contract ever for an outfielder) puts him well beyond the comfort zone of the Cubs’ previous large free-agent commitments (Jason Heyward’s $184M deal). The Cubs are now widely expected to lose Tucker.
- Bregman’s Fit: Bregman, a versatile All-Star third baseman, offers consistent offense, a winning pedigree, and defense at a fraction of Tucker’s projected cost.
What Bregman is Seeking Now
Bregman is testing the market for a second time to secure the long-term deal that eluded him last winter.
| Contract Prediction | Years | Total Value | AAV | Source |
| Prediction 1 | 5 years | $160 million | $32 million | NBC Sports |
| Prediction 2 | 6 years | $180 million | $30 million | Baseball America / SI |
The Cubs, who are prioritizing pitching but still need offense, now have a clear price range. A deal in the 5-6 year, $160M-$180M range would be a massive offensive addition for Chicago without crippling their budget and sacrificing their ability to fill other needs.
The question for the Cubs is whether they will increase their original four-year, $130 million offer to meet this new projected range and convince Bregman that Chicago is the right long-term destination.
