The Boston Red Sox were viewed as the favorite to keep Alex Bregman all throughout free agency right up until he signed with the Chicago Cubs. A new claim suggests the Red Sox overestimated their position, and it cost them dearly.
Former MLB catcher AJ Pierzynski claimed on the “Foul Territory” podcast that the Red Sox made Bregman an initial offer and refused to increase it, even when Bregman’s camp suggested that his market value was higher than what was being offered. When Bregman received his 5-year, $175 million offer from the Cubs, the Red Sox essentially thought he was bluffing.
“They made an offer to Alex Bregman early in the offseason, and his camp kept going back and saying, ‘That’s not our market. Our market’s higher than that,’” Pierzynski said. “It made Alex a little bit mad, and they would not move. The Red Sox were like, ‘Take it or leave it.’ They would not budge.
“Bregman’s camp goes back to them and says, ‘Hey, we have a higher offer and we’re going to probably take it.’ The Red Sox were like, ‘We don’t believe you. If you can do it, do it.’ (Bregman) said, ‘Okay, we’re going to sign. We’re not telling you the number. We’re going to sign with a different team.'”
At that point, the Red Sox took the threat seriously enough to increase their offer to 5 years and $165 million. That still did not match the Cubs’ offer.
Alex Bregman became frustrated with the Red Sox because they were unwilling to meet his market after their initial offer, says @AJPierzynski12.
— Foul Territory (@FoulTerritoryTV) January 12, 2026
The Red Sox then refused to believe Bregman's camp when they told them they had a better offer on the table. pic.twitter.com/cm8SlliYd1
Essentially, the Red Sox stubbornly misread the market and did not seriously think Bregman would leave. That approach alienated him, and when he got a higher offer, he jumped at it.
As high as a $35 million annual salary is, it is not that absurd for a player who has consistently been one of baseball’s best. He hit .273 with 18 home runs and 62 RBIs over 114 games last season and strongly endeared himself to Red Sox fans. There is a reason that Boston was widely expected to be aggressive and re-sign him, but the organization apparently took that for granted and paid for it.
