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    Brady Farkas
    Dec 16, 2025, 14:42
    Updated at: Dec 16, 2025, 14:48

    Does the trade for Jake Bennett mean something more is coming?

    On Monday night, the Boston Red Sox swung a surprising trade, sending No. 7-ranked prospect Luis Perales to the Washington Nationals for No. 11-ranked prospect Jake Bennett. Bennett is a left-handed pitcher who has spent much of his minor league career as a starter.

    On the surface, it's just an interesting trade: Prospect-for-prospect and two pitchers with a lot of potential who both have Tommy John surgeries in their recent histories.

    But underneath the surface, could there be something deeper?

    The Paul Toboni connection

    I want to give credit to Tyler Milliken of the Section 10 podcast, who reminds us that former Red Sox front office member Paul Toboni is the new general manager of the Nationals.

    Almost nobody is better versed in Red Sox prospects than he is, so the fact that he wanted Perales is noteworthy. Was there a disconnect between him and Craig Breslow in terms of how they valued Perales? Has that difference manifested itself in other players too? If so, is Breslow right in his evaluations or wrong? Those are questions that we'll want answers to, but likely won't get for several years.

    What this deal could mean

    Maybe there's no difference in evaluations, maybe it's just as simple as where these franchises are. The Red Sox are in a competitive window and as such, maybe they wanted the 25-year-old Bennett, who is ready to contribute this season. The Nationals are not expected to compete, so maybe they wanted the 22-year-old who is a few years away.

    Maybe it's that simple.

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    Or perhaps it means.....

    My head is spinning with this theory, but hear me out:

    If you look at the Red Sox' 40-man roster, it's littered with left-handed pitchers: Bennett, Patrick Sandoval, Garrett Crochet, Payton Tolle, Connelly Early and Kyle Harrison. Do the Red Sox really need that many or are they gearing up to move some of them in other deals and want Bennett there to backfill?

    For instance, we know the Arizona Diamondbacks want major league-ready pitching in a deal for Ketel Marte. Is there a chance that they like Bennett? Is there a chance they want Tolle, Early or Harrison and this is Breslow restocking the left-handed cupboard in advance of sending at least one of them out?

    The Sox have been linked to Marte, so perhaps this is the first chess move in making it officially happen.

    Up next

    The Red Sox can make a deal at any time, but it seems like if nothing gets done before the Christmas holiday, nothing will happen until after the new year. The baseball world usually rests between Christmas and New Years.

    But once January 1st hits, expect a flurry of deals with just six weeks until spring training.

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