Alex Bregman has proven to be as good a fit both on and off the field as the Boston Red Sox could’ve expected when they gave him a three-year deal ahead of the 2025 season. The only unfortunate reality to come with the Bregman experience is that it could be short-lived, as that three-year deal comes with an opt-out that he will almost certainly exercise at the end of this season, allowing him to test free agency again. The Red Sox want to ensure that he’ll remain in Beantown long-term, but it’ll cost them, based on what Jon Heyman of the New York Post ($) has reported.

“It’s rare a star of Bregman’s stature signs within months of unfettered (no qualifying offer attached) free agency. But there’s some chance, as both sides wouldn’t mind getting something done. The belief here is that with Bregman’s great start a deal would likely have to be around $184M (what he offered to sign with the Tigers), or perhaps even $200M,” Heyman wrote.

Bregman is open to remaining in Boston, but not at a discount. Chances are, if the Red Sox are open to acquiescing to Bregman’s steep demands, other players will have to depart by the time the 2026 campaign begins. These four players feel like safe bets in that regard.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.

4) Jarren Duran, outfielder

The Red Sox have more outfielders than spots right now, and that’s led to Jarren Duran’s name appearing in trade rumors. The Red Sox don’t have to trade him, but doing so would not only free them from their outfield logjam, but it’d allow them to fill other needs and save some money.

Duran isn’t expensive right now, but he has a club option worth $8 million in 2026 and then two arbitration years. He’s only going to get more expensive, and his price will obviously reach an all-time high following the 2028 campaign when he hits free agency.

The Red Sox have a good enough outfield to justify trading him, and dealing him would allow them to address another need or two with a cheaper option to fit Bregman in. Red Sox fans won’t like it, but it makes sense.

3) Aroldis Chapman, reliever

Nobody on this Red Sox roster has exceeded expectations more than Aroldis Chapman, who has a 1.18 ERA in 41 appearances and has converted all but one of his 18 save attempts. He’s hitting triple digits with his fastball consistently and has been as dominant as any reliever in the game. He’ll stick around for the remainder of the season with the Red Sox clearly making a postseason push, but beyond that, his future is very up in the air.

Chapman signed a one-year deal with Boston and is 37 years old. His performance this season has warranted a lucrative contract that will almost certainly be for multiple years. This bullpen might struggle without Chapman, but is it worth overpaying a reliever who will be 38 years old next season, especially after committing all that money to Bregman? Chances are, the Red Sox will go the cheaper route in the bullpen.

2) Walker Buehler, starting pitcher

Most of Boston’s offseason moves have aged tremendously, but the Walker Buehler signing has not. Buehler inked a one-year, $21.05 million deal with Boston, which has a $25 million mutual option for 2026. There was reason to believe that if he carried his postseason momentum into the 2025 campaign, the Red Sox would be willing to pick up their end of the mutual option. His struggles this year make it almost certain that the team will look to let him walk in free agency.

Buehler has a 6.12 ERA in 16 starts and 78 innings of work, and the advanced metrics don’t suggest he’s gotten all that unlucky. The Red Sox can get better and cheaper production by rejecting the mutual option and letting Buehler walk.

1) Lucas Giolito, starting pitcher

Red Sox fans didn’t expect much from Lucas Giolito after he missed all of last season due to injury and struggled to start 2025, but his recent production has been instrumental to the team’s turnaround. He has a 3.36 ERA in 13 starts overall, and has a 0.70 ERA in his last six appearances. He’s been awesome, and that’s made the option in his contract for next season very interesting.

Right now, Giolito has a $14 million club option for 2026, but that number rises to $19 million and becomes a mutual option if he can throw at least 140 innings this season. Right now, Giolito is at 72.1 innings with the entire second half in front of him. 140 innings is certainly possible.

Given how he’s pitched, it’ll be tough for the Red Sox to reject any option they have to keep Giolito in town, but a lucrative Bregman contract certainly makes it tougher for the team to commit to Giolito as well. It’ll be interesting to see just how much the Red Sox are willing to spend.