Why Alex Bregman Should Top $151 Million With Red Sox Opt-Out

If the Boston Red Sox want to continue their partnership with Alex Bregman, they are certainly going to have to pay up.

With reports surfacing hinting at an upcoming — and not shocking — opt-out by Bregman from Boston, the next question that naturally has popped up is how much could he potentially get on the open market?

Competition should be stiff for his services. The Red Sox obviously should be in the mix to bring Bregman back and a handful of other teams have already been speculated about, including the Detroit Tigers and Chicago Cubs, mainly. Both pursued him last year, but the Red Sox ended up winning the sweepstakes. There will be others as well after Bregman put together an All-Star campaign and helped to lead Boston back to the playoffs.

But, what could a deal look like? Let's take a look at Matt Chapman's six-year, $151 million deal with the San Francisco Giants as a starting point. Chapman -- also represented by Scott Boras -- joined the Giants on a deal with a far lower annual value ($18 million in comparison to $40 million for Bregman) with player options for the 2025 and 2026 seasons. Before he could opt out, though, the two sides agreed to a six-year, $151 million deal that began in 2025.

The Red Sox should call Alex Bregman quickly

Sep 30, 2025; Bronx, New York, USA; Boston Red Sox third base Alex Bregman (2) hits an RBI double during the ninth inning against the New York Yankees during game one of the Wildcard round for the 2025 MLB playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | Brad Penner-Imagn Images

Chapman is roughly one year older than Bregman. He's 32 years old and was born in April whereas Bregman is 31 years old and was born in March. Bregman will turn 32 years old around the time the 2026 season begins. Chapman turned 32 years old shortly after the 2025 season began, the first year of his big extension.

Chapman is a five-time Gold Glove Award winner, two-time Platinum Glove Award winner, and a one-time All-Star. He's a career .240 hitter with 203 homers as well. Bregman is a three-time All-Star, two-time World Series champion, one-time Gold Glove Award winner, and a one-time Silver Slugger Award winner. He's a career .272 hitter with 209 homers.

For Bregman, he signed a three-year, $120 million deal with Boston -- although some of that cash was deferred. If we simply look at the annual value, that's $80 million left over two years. Chapman got a six-year deal at pretty much the same age with Boras as a client. Bregman arguably is a better overall player with championship pedigree. It's hard to see him not getting a six-year deal as well.

Chapman's annual value is just north of $25 million. For Bregman, he should get higher. If you were to take that $80 million left on his deal and tack on four extra years and $100 million, that seems like a fair value in comparison. Bregman would get his six-year deal and a higher annual value than Chapman. If you erase those two years and just call it a six-year, $180 million deal worth $30 million per year with higher payouts towards the beginning of the contract, that should be fair for both sides.

There will be competition for him. Maybe someone does get close to $200 million to really try to get a deal done. But, with Chapman's deal as an example from Boras, this seems like fair and is something the Red Sox should make a call about as soon as possible.

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