Red Sox begin offseason with Nate Eaton trade as Gray, Whitlock decisions await

The 2026 Major League Baseball season officially ended Wednesday night, with the Milwaukee Brewers capturing their first World Series championship in franchise history after defeating the Tampa Bay Rays in five games. 

It was a World Series matchup between two small-market clubs that don’t have the financial resources to compete with big spenders like the Dodgers, Yankees, Mets, Cubs, and Red Sox in free agency. 

The Brewers, led by Jacob Misiorowski, the favorite to win the National League Cy Young Award, World Series MVP William Contreras, Jackson Chourio, Cooper Pratt, and others built a championship-caliber roster through shrewd trades, strong drafting and international signings, rather than opening their checkbook in free agency. In fact the Brewers signed just one Major League free agent last offseason in Gary Sanchez. 

Milwaukee sent a resounding message to baseball’s financial heavyweights by sweeping the Dodgers in four games in the National League Championship Series, ending Los Angeles’ pursuit of a third consecutive World Series title. 

Tampa Bay reached the World Series with a similar approach in their roster construction. Both organizations demonstrated that teams can be successful with smaller payrolls while competing with the powerhouses around the game. 

With the Fall Classic officially in the books, Major League Baseball has entered the offseason. Teams now have a five-day exclusive negotiating window with their pending free agents before those players can begin negotiating with other clubs.

It figures to be an interesting few weeks around baseball, particularly with a potential lockout looming when the current collective bargaining agreement expires on Dec. 1.

The Brewers have barely had time to wipe the champagne from their eyes following their first World Series championship, and Craig Breslow has already made his first trade of the offseason.

The Red Sox are sending outfielder Nate Eaton to the Athletics in exchange for 18-year-old pitching prospect Jareth Rayo, according to multiple reports.

The deal marks the first trade between Breslow and new Athletics president of baseball operations Taylor Smith, who recently departed Boston's front office to take over baseball operations for the franchise preparing to relocate to Las Vegas.

For the Red Sox, the move clears a spot on the 40-man roster ahead of an offseason in which the organization faces several decisions regarding players on the roster bubble.

Eaton, who turns 30 in December, appeared in 65 games for Boston over the past two seasons, batting .244 with two home runs, 10 RBI, 11 stolen bases and a .560 OPS.

He provided defensive versatility, appearing at all three outfield positions and third base during his time with the Red Sox.

Eaton also earned a spot on Boston's postseason roster for both Wild Card Series losses to the Yankees. This October, he went 3-for-7 with two doubles.

He spent the majority of the 2026 season at Triple-A Worcester, where he hit .253 with nine home runs, 16 doubles, 44 RBI and a .748 OPS.

However, Eaton was out of minor league options, meaning Boston could no longer send him to Worcester without first exposing him to waivers.

Had the Red Sox attempted to outright him off the 40-man roster, there was a reasonable chance another organization would have claimed him, given his defensive versatility and above-average speed.

Rather than risk losing Eaton for nothing, Breslow was able to acquire a young pitching prospect while creating additional roster flexibility.

In return, Boston receives Rayo, a 6-foot-3, 195-pound right-hander who signed with the Athletics out of Nicaragua during the previous international signing period.

Rayo, who turns 19 on Nov. 16, spent the 2026 season in the Dominican Summer League, posting a 5.50 ERA over 36 innings.

While Rayo remains several years away from the major league level, the trade gives Boston another young arm to develop within its minor league system. He's nothing more than a lottery ticket for Boston. 

With several 40-man roster decisions still looming and the possibility of a lockout just weeks away, it likely won't be the last move Boston makes before baseball's offseason activity potentially comes to a halt.

Free Agents

With the World Series officially in the books, Major League Baseball's offseason is underway, and 144 players elected free agency Thursday, including two members of the Red Sox.

Infielder Isiah Kiner-Falefa and left-hander Patrick Sandoval are officially on the open market, and neither appears particularly likely to return to Boston in 2027.

Patrick Sandoval

The Red Sox signed Sandoval to a two-year contract two offseasons ago, knowing he would miss significant time recovering from Tommy John surgery.

The left-hander didn't make his Boston debut until earlier this season, eventually settling into a role at the back of the rotation.

Sandoval showed some encouraging signs early, posting a 3.30 ERA through his first six outings. However, his performance declined as the season progressed, and he finished with a 6.47 ERA across his final stretch of starts.

While Sandoval provided innings as a No. 5 starter, Boston has several pitchers competing for rotation spots heading into next season.

Garrett Crochet, Brayan Bello, Tanner Houck, Payton Tolle, Jake Bennett and Johan Oviedo are all expected to factor into the rotation picture, leaving little room for Sandoval. Given the organization's pitching depth and Sandoval's struggles during the second half, his time in Boston appears to have come to an end.