For the first time in franchise history, the Milwaukee Brewers are World Series champions, defeating the Tampa Bay Rays in five games. With the offseason officially underway, the Boston Red Sox have a lot of work to do in a short time, facing an impending roster crunch and decisions on two key pitchers, all while trying to build a World Series contender. 

Among the league's first orders of business is the start of free agency. On Thursday, the Major League Baseball Players' Association announced that 144 players are officially free agents, including two 2026 Red Sox players, Patrick Sandoval and Isiah Kiner-Falefa. 

Here's what you need to know: 

After signing a two-year, $18.5-million deal with Boston ahead of the 2025 season, Sandoval spent much of his time in Boston rehabbing from the 2024 Tommy John surgery he underwent as a member of the Los Angeles Angels. The 29-year-old made his long-awaited Red Sox debut on July 9 against the Chicago White Sox. 

In 15 appearances (13 starts), serving primarily as Boston’s fifth starter, Sandoval posted a 1-7 record with a 5.12 ERA over 70.1 innings, striking out 9.3 batters per nine innings and walking 4.1 per nine. While his ERA doesn’t jump off the page, a fielding-independent pitching (FIP) of 3.77 suggests he was the victim of some bad luck.

Sandoval performed well as an innings-eating fifth starter. However, with a crowded back end of the Boston rotation, it’s hard to imagine the left-hander back in Boston in 2027.  

After spending the 2025 season with the Toronto Blue Jays, the 31-year-old utility man signed a one-year, $6-million deal to join the Red Sox in pursuit of a World Series title. 

Kiner-Falefa performed well in what could be his lone season in Boston, hitting .244/.322/.311/.633 in 66 games, providing plus defense across the infield. He was especially impactful after veteran shortstop Trevor Story landed on the injured list with a sports hernia, hitting .321/.391/.449/.840 in 26 games as Boston’s primary shortstop before he himself landed on the injured list with a forearm injury. When he returned on Sept. 1, Kiner-Falefa struggled at the plate, hitting .143/.265/.167/.432 in 19 games. 

Like Sandoval, Kiner-Falefa's return to Boston in 2027 is hard to imagine, as it looks like there will be tight competition among Andruw Monasterio, Nick Sogard, Romy Gonzalez, and Anthony Seigler for the bench utility role.

Kiner-Falefa and Sandoval will have five days to negotiate a potential return to the Red Sox. If the teams are unable to come to an agreement by Nov. 2, both players will be free to sign elsewhere when free agency officially begins.  

Sandoval and Kiner-Falefa may not be the last 2026 Red Sox players to hit free agency. The team has to decide on options for two key pitchers. Reliever Garrett Whitlock has a team option worth $8.25 million that the team will likely exercise. Starter Sonny Gray has a mutual option worth $30 million for 2027, with a $10 million buyout. Gray will likely decline his side of the option, collect his buyout, and hit the open market in search of a multi-year deal. Decisions on both options must be made by Nov. 2. 

The Red Sox kicked off the offseason with two roster moves. First, the team re-signed relief prospect Angel Bastardo to a minor-league deal with an invite to major-league spring training. The 24-year-old spent the 2026 season with the Triple-A Worcester Red Sox, posting a 4.64 ERA in 40 appearances over 54.1 innings pitched.

Boston also swung the first trade of the offseason, sending outfielder Nate Eaton to the Athletics in exchange for pitching prospect Jareth Rayo. In 24 regular-season games with Boston in 2026, the 29-year-old hit just .160/.300/.260/.560 with one home run and two doubles, driving in six runs.