The Boston Red Sox had their sights on two significant upgrades this offseason, only to see both slip through their grasp. Most notably, slugging outfielder Anthony Santander landed with their division rivals, the Toronto Blue Jays, on a deal worth over $90 million. Santander’s addition to the Blue Jays lineup adds an immediate threat, giving Toronto a potent power bat to slot into the heart of their order.

For the Red Sox, missing out on Santander is a painful blow, especially given his consistent production. The 31-year-old switch hitter delivered a standout 2024 campaign with the Baltimore Orioles, slashing .235/.308/.506 with 44 home runs, 102 RBIs, and a 129 wRC+. Known for his ability to perform in clutch situations, Santander represented the type of offensive firepower the Red Sox could have used to elevate their lineup.

Boston’s outfield depth is still in decent shape, but losing Santander to a divisional rival only sharpens the stakes. His arrival in Toronto signals that the Blue Jays are aggressively trying to build their roster, but they’ve also struggled to lure talent up North this offseason.

Missing Out on Tanner Scott

On the pitching front, Boston also fell short in their pursuit of elite left-handed reliever Tanner Scott, who signed a four-year, $72 million deal with the Los Angeles Dodgers. Scott would have been a vital addition to a Red Sox bullpen that has struggled with consistency.

Scott, coming off an impressive season with the Marlins and Padres, posted a 1.75 ERA across 72 innings, striking out 10.50 batters per nine. His ability to dominate in high-leverage situations made him one of the most coveted relief arms this offseason, and his loss stings even more given Boston’s recent trade acquisition of Garrett Crochet. Pairing Scott with Crochet could have created a devastating left-handed duo capable of shutting down any lineup as a combo punch.

The Road Ahead for Boston

The Red Sox are now left reeling after missing out on two premium targets. Santander’s move to Toronto not only weakens Boston’s own offensive outlook but strengthens a rival’s. Meanwhile, Scott’s deal with the Dodgers ensures that one of the best bullpen arms in the league is off the table, leaving Boston scrambling to find alternative solutions

Boston’s front office has already made significant moves this offseason, but with these two misses, they’ll need to pivot quickly to avoid falling behind in the ever-competitive AL East race. The question now is whether they can regroup and strike before the remaining top-tier talent is gone.