Last offseason, the Boston Red Sox lost a key member of their front office after the Washington Nationals signed Paul Toboni to be their President of Baseball Operations. Toboni was a rising star in the Red Sox front office and one of Craig Breslow's closest confidants. The Red Sox were able to move forward without him, but now it seems like the Red Sox are on the verge of losing another key piece at the top.
A recent report by ESPN's Jeff Passan indicated that one of Boston's Assistant General Managers, Taylor Smith, was a top candidate to be named the Athletics President of Baseball Operations. If that comes true, it would be the second AGM Boston has lost in two years, and another one of Breslow's closest staff members gone.
Smith joined the Red Sox from the Tampa Bay Rays in October of 2024. His role in Tampa was "Director, Predictive Modeling," a role he got in December of 2021. His role was defined as overseeing "the organization's player valuation models and provides mentorship and oversight to baseball research and development staff." He is obviously someone who stays more on the analytics side.
The A's could be looking at him specifically because he has worked in two organizations that excel in pitching development, something they have struggled with mightily. The Rays have long been known for being able to get the most out of pitchers, and the Red Sox under Breslow have done an amazing job in the pitching development department.
There are pros and cons to a potential departure of Taylor Smith
Boston assistant general manager Taylor Smith remains a top candidate to take over as head of baseball operations for the A’s, sources tell ESPN. Cardinals assistant GM Rob Cerfolio, another finalist, is expected to remain with St. Louis.
— Jeff Passan (@JeffPassan) October 10, 2026
While Smith has only been in the organization for two years, that would be a deep blow to Breslow's front office. Smith has been one of Breslow's few high-ranking hires in his tenure, with a lot of the other AGMs having been around for multiple regimes.
This would certainly force Breslow to make other hires if it happens, which is not necessarily a bad thing. His front office has been described as having a close circle of trust that didn't always include all of the high-ranking members. Smith certainly would have been in that circle as someone Breslow handpicked.
Red Sox front office staff being hired elsewhere isn't a bad sign either. Being an organization that can develop front office personnel is a good trait to have. That means the organization is succeeding, which it has for the last two years, and that the right people are being hired and promoted. Also, Breslow made a few trades with Toboni last season; it wouldn't be the worst thing to have another disciple in another organization.
Seeing Smith hired elsewhere would be bittersweet. While fans can always hope their top officials want to stay around to continue the success the organization is having, top talent needs to shine and get their opportunities.
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