With the Major League Baseball Winter Meetings scheduled for Dec. 7 through Dec. 11 in Orlando, FL, quickly approaching, the Boston Red Sox may be looking to swing a trade with a team from the Sunshine State. After all, the annual meetings give general managers and front office executives face-to-face opportunities to wheel and deal before heading into the spring.
Interestingly enough, the Red Sox’s best potential trade partner might be an unlikely franchise.
Following five straight postseason appearances from 2019 to 2023, the Tampa Bay Rays have missed out on October baseball in their last two campaigns. As the Rays look to right the ship and re-establish themselves as a perennial playoff team, several Tampa Bay players have been at the center of trade speculation. From Boston’s perspective, two of the players on the Rays’ chopping block are enticing roster fits, making Tampa Bay an attractive trade partner.
Could Red Sox Target a Two-Time All Star During Winter Meetings?
Rays second baseman Brandon Lowe has been one Rays player who’s been linked to a trade out of Tampa Bay. After two consecutive top-10 MVP finishes in 2020 and 2021, Lowe’s production had started to dwindle, but he enjoyed a resurgent 2025. The career Ray hit 31 home runs while driving in 83 runs while earning his second All-Star nod (his first since 2019).
Lowe will be a free agent following the 2026 season, furthering the belief that his days with the franchise may be numbered, as the Tampa Bay front office will be more inclined to move him now than risk him walking out with no return at the end of next season.
Beyond the addition of Lowe’s offensive production, he would also boost the Red Sox defensively by allowing them to solidify Gold-Glover Ceddanne Rafaela as their everyday centerfielder. Rafaela was forced into action at second base 24 times in 2025 due to injuries and inconsistent play from Red Sox second basemen. Pairing Rafaela with another Gold Glove winner, Wilyer Abreu, in right field would give Boston one of the premier defensive outfields in baseball.
Alex Bregman’s offseason decision could also have ramifications on Lowe’s fit in Boston. Should Bregman depart, Marcelo Mayer would appear to be the everyday third baseman, and the door for Lowe at second would remain vacant. Should Bregman return, Mayer’s defensive positioning would become murkier, and he might split time between second and third.
While Lowe would provide the Red Sox with a huge boost, he isn’t the only Ray that the front office should try trading for in Orlando.
Yandy Diaz Might Be the Solution Red Sox’s 1B Questions
Rays first baseman and former batting champion Yandy Diaz has been another Tampa Bay player linked to the Red Sox. Boston reportedly checked in on Diaz at the 2025 deadline and was “high” on the right-handed hitting first baseman, per Chris Cotillo of MassLive. The 34-year-old slashed .300/.366/.482 with 25 home runs and 83 RBI last season. His bat would be a welcome addition to a left-handed heavy lineup, even as rumors surrounding the Red Sox and Pete Alonso pick up steam.
First base has been a game of musical chairs for the Red Sox over the last two seasons, largely due to significant injuries suffered by Triston Casas. Casas showed promise as Boston’s first baseman of the future — finishing third in the American League Rookie of the Year voting in 2023 — but has only appeared in 92 games since due to injury. His future with the club is a massive question mark. Perhaps adding Diaz could help to answer that question mark (and maybe spell the end for Casas in Boston).
Intra-divisional trades are often met with skepticism for obvious reasons, but the Rays may be more agreeable to trading with their American League East rival, given their current standing in the division and historical reluctance to spend in free agency. The Red Sox also have plenty of talented prospects to tempt them, which is why they can’t leave Orlando without making a deal with the Rays.
