Last offseason, the Boston Red Sox front office took a major hit when Assistant General Manager Paul Toboni became President of Baseball Operations for the Washington Nationals. Along with losing Toboni, who played a major role in amateur scouting and minor league development, Boston also lost its head of amateur scouting, Devin Pearson, who left for an Assistant General Manager role in Washington, along with several other front-office pieces. 

After major success in player development and building one of the best farm systems in baseball over the last five years, brain drain is natural. Now, just one year after losing Toboni and Pearson, the Red Sox risk losing another major piece of the organization, as ESPN's Jeff Passan reports that Assistant General Manager Taylor Smith has emerged as the top candidate to take over baseball operations for the Athletics. 

Smith's emergence as the top target for the Athletics, who fired long-time general manager David Frost in August, comes after Philadelphia Phillies President of Business Operations Sam Fuld was offered the job and turned it down. 

A former member of the Tampa Bay Rays research and development team, Smith was poached by the Red Sox in October 2024, when Breslow named him assistant general manager. In two seasons with Boston, Smith headed Boston's analytics department, which, for better or worse, has become a major priority under Breslow. 

While nothing is finalized between the two sides, losing Smith, along with whoever he brings with him in elevated roles, would be a major blow to the Red Sox front office as they enter a crucial offseason. 

As reported by Gabrielle Starr of the Boston Herald, reliever Garrett Whitlock suffered a fractured tibia sometime in the final month of the season. Whitlock had been pitching through leg discomfort throughout September; however, he didn't discover the break until he underwent imaging at the end of the season. Despite pitching on a broken leg, Whitlock allowed no earned runs in eight September appearances. 

In the waning weeks of the regular season, Red Sox starter Sonny Gray had been open about possibly retiring after his 14th major league season. On Friday night, Gray put that talk to rest, announcing that he would be returning for a 15th season in 2027. Gray and the Red Sox must decide on the $30 million mutual option for the 2027 season. If either side declines, the 36-year-old will receive a $10 million buyout and hit the open market. Teams and players have until five days after the World Series ends to make their decisions on options.