Apr 29, 2021; Arlington, Texas, USA; A view of the Boston Red Sox logo and a field bag during batting practice before the game between the Texas Rangers and the Boston Red Sox at Globe Life Field. Mandatory Credit: Jerome Miron-Imagn Images Jerome Miron-Imagn Images

4 Red Sox Enter Free Agency After Boston's Best Season Since 2021

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Nov 3, 2025 9:00 AM ET

The World Series and 2025 Major League Baseball season is now fully behind us, meaning that it's time to think ahead to 2026.

The Boston Red Sox had a successful season in 2025. They didn't hoist the World Series trophy, but they took significant steps towards that idea. Boston won 81 games in 2024 and that number jumped all the way up to 89 in 2025 after adding guys like Garrett Crochet, Alex Bregman, Aroldis Chapman, and the promotions of Roman Anthony and Marcelo Mayer during the season. Also, Kristian Campbell was a key piece at the beginning of the season.

The Red Sox had their best overall season in 2025 since 2021. That year, the Red Sox won 92 games and made to the American League Championship Series. The Red Sox didn't make it that far this year, but the team proved it has the right core in place for 2026 and beyond.

All in all, the Red Sox are in a better position right now than they were a year ago. But, that doesn't mean it is time to get complacent. There are decisions to be made. Boston already has four guys heading to free agency with more to come. With the World Series now over, pending free agents officially were scheduled to enter the market on Sunday, per MLB.com's Todd Zolecki.

"Officially, players become free agents the day after the end of the World Series," Zolecki said. "It could be Saturday, if the Blue Jays win Game 6 on Friday night. Or it will be Sunday, if the Dodgers force a Game 7. Free agents cannot sign with a new team until 5 p.m. ET on the fifth day after the conclusion of the World Series. Teams can re-sign their own players at any point during that five-day period, although it rarely happens."

Who will be back for Boston?

For Boston, this is in reference to Dustin May, Steven Matz, Justin Wilson, and Rob Refsnyder. May came over from the Dodgers in a trade deadline swap and it would be somewhat surprising to see him back. Refsndyer, on the other hand, seems like the most likely of the group to return. Alex Speier of the Boston Globe reported that Refsnyder isn't retiring and has had "informal" talks about a return.

Matz and Wilson both had success out of the Boston bullpen in 2025. Matz came over in a deadline swap and Wilson was with the team all season.

Wilson had a 3.31 ERA in 61 appearances. Matz had a 3.05 ERA in 53 total appearances. He was at his best in Boston with a 2.08 ERA in 21 outings. Bringing back both arguably would be a good move to maintain the bullpen's continuity into 2026 after it was a weapon in 2025.

There's more to come with option decisions due within five days of the World Series, but these are the Red Sox's free agents, for now.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

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