Bregman’s $120M Red Sox Contract Stretches Through 2046

17 Feb at 7:14 pm

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Bregman’s $120M Red Sox Contract Stretches Through 2046 \ Newslooks \ Washington DC \ Mary Sidiqi \ Evening Edition \ Alex Bregman’s new three-year, $120 million contract with the Boston Red Sox includes $60 million in deferred payments, meaning he could receive his final paycheck in 2046. His $5 million signing bonus is set for 2028, and his annual salaries of $35 million (2024) and $40 million (2025-26) are partially deferred to lower Boston’s luxury tax hit. The two-time All-Star and Gold Glove winner can opt out after 2025 or 2026, potentially re-entering free agency.

Quick Looks

Bregman Signs $120M Contract With Red Sox: The three-year deal includes $60 million in deferred payments, extending through 2046.
Deferred Payments Reduce Payroll Impact: Boston will pay $20 million per year in deferrals between 2035 and 2046, lowering the contract’s luxury tax hit.
Opt-Outs After 2025 and 2026: Bregman can re-enter free agency if he chooses to leave after either of the next two seasons.
$5M Signing Bonus Delayed Until 2028: Unlike most deals, his signing bonus won’t be paid until 2028, adding to the long-term payment plan.
Red Sox Unclear on Bregman’s Position: With Rafael Devers at third base, Bregman may need to shift to second base or another role.
Bregman Leaves Astros After Nine Seasons: The two-time All-Star and World Series champion hit .260 with 26 home runs and 75 RBIs in 2023.
Deferred Contracts Becoming More Common in MLB: Similar long-term payment structures have been used for Mookie Betts, Bryce Harper, and Max Scherzer.
Bregman Will Be Paid for 20+ Years: The deal ensures he will continue earning from Boston well into retirement, making it one of MLB’s longest payout contracts.

Deep Look

Alex Bregman’s new three-year, $120 million contract with the Boston Red Sox is structured in a way that will keep him earning money from the team for more than two decades, with $60 million of his total salary deferred until 2046. The deal, which was announced Saturday, is designed to lower Boston’s competitive balance tax (luxury tax) impact while providing Bregman with long-term financial security well beyond his playing years.

Under the agreement, Bregman will earn $35 million in 2024 and $40 million in both 2025 and 2026, but $20 million from each of those seasons will be deferred. The payments will be distributed between 2035 and 2046, with a structured payout that increases in value over time before tapering off. Additionally, his $5 million signing bonus won’t be paid until January 15, 2028, further delaying some of his earnings.

By deferring a significant portion of his salary, the Red Sox reduce the contract’s average annual value (AAV) for luxury tax calculations, allowing them to maintain greater payroll flexibility. This financial strategy has become increasingly common in Major League Baseball, as teams look for ways to retain star players while managing their salary cap obligations.

Opt-Out Clauses Provide Bregman Flexibility

Bregman’s contract includes opt-out clauses after both the 2025 and 2026 seasons, meaning he can choose to become a free agent again before the deal expires. If he performs at an elite level over the next two seasons, he could leverage the market for an even more lucrative long-term contract, rather than waiting for the deferred payments to kick in.

Given that MLB salaries continue to rise, Bregman’s opt-outs could be strategically beneficial. If other infielders sign record-breaking deals in the next two years, he may decide to test the market once again in hopes of securing a longer, higher-value contract elsewhere.

Bregman’s Role With Red Sox Still Unclear

Now 30 years old, Bregman leaves the Houston Astros after spending nine seasons with the team. A two-time All-Star, two-time World Series champion, and a Gold Glove winner in 2023, he remains one of the game’s most reliable infielders. Last season, he hit .260 with 26 home runs and 75 RBIs, providing a steady offensive presence while continuing to shine defensively.

However, his position in Boston remains uncertain. Traditionally a third baseman, Bregman joins a team where Rafael Devers has held that role since 2017. This raises questions about whether he will shift to second base, rotate positions, or potentially serve in a designated hitter role. While the Red Sox have not made an official statement about where Bregman will play, his versatility in the infield may allow him to adapt to a new role if needed.

Deferred Contracts Becoming More Common in MLB

The structure of Bregman’s contract follows a growing trend in Major League Baseball, where teams defer large portions of player salaries to ease luxury tax burdens and maintain payroll flexibility. This approach has been seen in several high-profile contracts, including those of Mookie Betts, Max Scherzer, Bryce Harper, and Manny Machado, all of whom have deferred earnings well beyond the expiration of their playing careers.

By spreading out payments over an extended period, teams can allocate resources more effectively, while players benefit from continued income long after retirement. In Bregman’s case, his final paycheck from the Red Sox will come in 2046, meaning he will still be collecting payments well into his 50s.

What’s Next for Bregman and the Red Sox?

With Bregman now under contract, the Red Sox must determine how to integrate him into their lineup. His ability to play both third base and second base gives the team some positional flexibility, but it remains to be seen how manager Alex Cora will adjust his infield configuration.

At the same time, Bregman’s presence adds veteran leadership to a Red Sox team looking to return to playoff contention. Boston’s long-term financial strategy with this deal also suggests that they are focused on maintaining financial flexibility while securing top talent.

Whether Bregman ultimately plays out the full contract or exercises his opt-out clauses, his deal represents a significant investment in both his future and Boston’s payroll management strategy. As MLB contracts continue to evolve, Bregman’s heavily deferred deal may serve as a blueprint for future negotiations, balancing immediate competitive goals with long-term financial planning.