The 2026 offseason saw two of baseball’s biggest free agents, Pete Alonso and Alex Bregman, sign major contracts that surprised many within MLB circles. Alonso agreed to a five-year, $155 million contract with the Baltimore Orioles, while Bregman committed to the Chicago Cubs on a five-year, $175 million deal. These signings reshaped expectations for the league’s top talents and shifted team dynamics heading into the new season.
Agent Scott Boras, representing both players and numerous other stars, provided an in-depth look at the negotiation process in a recent appearance on The Show. His insights revealed the personal and strategic reasons behind these landmark agreements.
Agent Scott Boras Details Family and Team Dynamics Influencing Contracts
Scott Boras explained that Bregman’s contract negotiations were heavily influenced by his role as a husband and father of two young children. Boras noted that the Cubs carefully considered these factors, making sure the contract addressed not only financial terms but also personal provisions valuable to Bregman and his family.
“When negotiating in good faith, we obviously laid out to all teams what Alex Bregman’s needs were. Primarily, as a father and a husband, there’s no question, he has two young children. The idea of this is you lay it out, and you lay out the importance of it. Everybody had notice of it, and Alex and (Alex Bregman’s wife) Reagan felt, after review of all this, that the Cubs certainly listened to them, and included in their contract provisions that allowed them the most favorable treatment for their situation,” Boras said (57:41).
Boras also highlighted the strategic calculations behind Alonso’s move to Baltimore. He spoke about the potential Alonso and Orioles outfielder Gunnar Henderson have to form a dynamic duo similar to other powerful MLB pairings. The Orioles’ commitment to Alonso signified their desire to build a formidable offensive core.
“When you have a talent like Pete, the one thing I felt was that the combination of him and Juan Soto, and I told (Mets owner) Steve Cohen this, knowing Juan and Pete, our algorithmic computations were that these two were going to be magical. And it turned out that way. I think a number of teams took notice of that. You got (Aaron) Judge and (Cody) Bellinger, you got (Shohei) Ohtani and (Mookie) Betts, you got this combination where a group of players were phenomenal. The one thing that became clear was that Baltimore felt with Gunnar Henderson and Pete Alonso, they were that combination. That’s why Mike Elias really made Pete a priority,” he added (59:20).
How Alex Bregman’s Leadership Boosts Cubs’ Long-Term Vision
Beyond the figures involved in these contracts, intangible qualities have played a vital role, especially for the Cubs with Bregman. Chicago sportscaster Matt Spiegel of 670 The Score emphasized the importance of Bregman’s clubhouse presence, comparing it favorably to veteran Justin Turner, who was retained largely for his leadership.
“They kept Justin Turner on the roster all year because he brought that (clubhouse presence), and they admitted that it was important,” Spiegel said (20:37).
Spiegel argued that Bregman could provide an even stronger fit in the clubhouse combined with his on-field production, similar to how Kyle Schwarber earned legendary status with the Cubs.
“This (Bregman) is a better fit than Justin Turner. This is why Schwarber is a legend, because Schwarber has all of that and produces. If Bregman has all of that and produces, that’s when the value really jumps up,” he added.
During his 2025 season with the Boston Red Sox, Bregman batted .273 with 18 home runs and 62 RBIs, earning All-Star honors while helping Boston reach the postseason, setting expectations high for his tenure in Chicago.
Comparisons of Strategic Player Pairings in MLB
In his commentary, Boras referenced key player duos around the league, noting the splash made by pairs like Mets’ Juan Soto and Pete Alonso, as well as Judge and Bellinger in New York and Shohei Ohtani paired with Mookie Betts in Los Angeles. These tandems have shifted power balances and influenced teams’ approaches to roster building.
With Baltimore’s Alonso and Gunnar Henderson seen as an emerging powerful combination, Orioles General Manager Mike Elias placed significant importance on securing Alonso, anticipating this pairing to elevate the team’s competitive standing.
The Broader Impact of These High-Profile Signings on MLB
The signings of Pete Alonso and Alex Bregman mark a turning point in MLB’s free agency landscape, showcasing how personal considerations, team strategy, and statistical analysis converge to shape player destinations. Alonso’s agreement with the Orioles surprised many teams that expected him to remain with the Mets or move to a more established franchise, while Bregman’s deal reflects the Cubs’ commitment to recreating a competitive atmosphere through talent and leadership.
With the 2026 season approaching, fans and analysts alike will be watching closely to see how these players influence their new teams, both on and off the field. Their performances—and the chemistry they develop with teammates—could set new standards for what is expected in high-value MLB contracts.
