Inside The Red Sox

Best And Worst-Case Scenarios For Red Sox's Alex Bregman Chase

The Boston Red Sox need to get into the action...
Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) at bat against the New York Yankees during the third inning at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images
Aug 22, 2025; Bronx, New York, USA; Boston Red Sox third baseman Alex Bregman (2) at bat against the New York Yankees during the third inning at Yankee Stadium. Mandatory Credit: Gregory Fisher-Imagn Images | Gregory Fisher-Imagn Images

The Boston Red Sox are a team that very much is under microscope right now.

While the club has done some good things in the starting rotation by acquiring Sonny Gray and Johan Oviedo, there is still work to be done. The club itself has openly spoken about a need to add at least one or two bats. Boston was heavily linked to Kyle Schwarber in a heap of rumors dating back to the beginning of the offseason but he opted to stay in Philadelphia. The Red Sox were one of the teams in on the Pete Alonso sweepstakes -- and even met with him -- but couldn't get a deal done. On the offensive side, there's been a lot of talk, but not a lot of follow-through.

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That was especially on display in the Alonso sweepstakes. Alonso got a five-year, $155 million deal from the Baltimore Orioles. Tim Healey of the Boston Globe reported that Boston's offer was for "fewer years and significantly less money."

The Red Sox need to get moving

Now, the attention has turned to the Alex Bregman sweepstakes and there's a lot of noise out there. On Tuesday, things heated up. USA Today's Bob Nightengale reported that the Arizona Diamondbacks have become a "surprise entrant" in the Bregman sweepstakes. On the bright side, Ken Rosenthal of The Athletic said the Diamondbacks "almost certainly" would need to trade Ketel Marte to be able to afford Bregman.

With things heating up around the league, what would be the best- and worst-case scenarios for Boston? Let's dive in.

Best-Case

This one is pretty obvious. Signing Bregman to a long-term deal would be the best-case scenario. On Tuesday, Ari Alexander of 7News Boston WHDH reported on the Bregman sweepstakes and noted that a similar three-year deal to the one Bregman got with Boston last offseason wouldn't get the deal over the finish line. If Boston wants Bregman, it is going to need to pay up. ESPN's Kiley McDaniel shared an updated contract projection for Bregman and predicted that his market is in the range of $170 million over five years. If that's close to accurate, there's no reason why Boston shouldn't get it done. Offer it now and see what happens. A five-year deal at the money should be perfectly affordable for Boston after trading Rafael Devers and landing two pitchers via the trade market.

Worst-Case

Boston keeps waiting for the perfect deal. If McDaniel's projected price is accurate, that is obviously a lot. The Red Sox signed Bregman last February to the short-term pact. At the time, it looked like a steal. Now, Bregman doesn't have the qualifying offer attached to him. Other teams -- including the Chicago Cubs and Detroit Tigers -- have been linked to Bregman. Now, the Diamondbacks are dipping their toes in the water.

The worst-case scenario is that the Red Sox wait so long that they miss on other top free agents (like Bo Bichette) or even trade chips (like Marte) and the time on the market allows Bregman the chance to find a better deal elsewhere. Imagine the outcry if the Red Sox were to lose Bregman and miss out on the other top free agents? Right now, that's the trend.

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Patrick McAvoy
PATRICK MCAVOY

Patrick McAvoy's experiences include local and national sports coverage at the New England Sports Network with a focus on baseball and basketball. Outside of journalism, Patrick received an MBA at Brandeis University. For all business/marketing inquiries regarding Boston Red Sox On SI, please reach out to Scott Neville: scottneville21@gmail.com

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