The offseason has been productive for Craig Breslow and the Boston Red Sox, with a more aggressive approach than we’ve typically seen from the team. Garrett Crochet and Walker Buehler are expected to bolster a struggling rotation, putting Boston in a strong position for the postseason despite the tough competition in the AL East.
However, many of the lingering questions about the Red Sox center around “what if” scenarios. While the team has spent money, missing out on Juan Soto, Max Fried, and now Teoscar Hernandez feels like a setback, even though the roster has improved.
Hernandez, in particular, had strong ties to Boston in the lead-up to his decision to re-sign with the Los Angeles Dodgers. Soto and Fried were long shots, but Hernandez was within Boston’s budget and filled a clear need, providing right-handed power to balance their lefty-heavy lineup.
Ultimately, Hernandez chose the reigning champs with a three-year, $66 million deal, including over $23 million in deferred payments and a $15 million option for a fourth year.
Now, Boston is left searching for alternatives as the free-agent market shrinks. Here are a few realistic backup options for Breslow to consider.
3. Luis Robert Jr. is an easy trade target for the Red Sox
Having already completed one major trade this winter, Craig Breslow and Chris Getz may be inclined to make another. The Red Sox, with a deep pool of top prospects and a clear intention to compete, are in a strong position to make a move. Meanwhile, the Chicago White Sox, coming off a historically poor season, are looking to rebuild their farm system. Luis Robert Jr. seems like a natural target for Boston.
The Red Sox still need a prominent right-handed bat to balance their lineup, and Robert could be the answer. While he struggled last season with a .224/.278/.379 slash line, 14 home runs, and 23 stolen bases in 100 games, it’s important not to read too much into those numbers. Robert was dealing with a lingering hip injury, which affected his performance.
Looking back at 2023, Robert posted an impressive .857 OPS — 200 points higher than in 2024 — with 38 home runs and 20 stolen bases, landing him 12th in AL MVP voting. At just 27 years old, Robert still has plenty of upside, and if he regains his health and form, the Red Sox could have a long-term cleanup hitter on their hands. His contract includes affordable $20 million club options for 2026 and 2027, meaning Boston could get three full years of his contributions.
The combination of age, contract, and potential makes Robert an appealing target. While there’s certainly risk, Robert is likely due for a bounce-back season, especially in a competitive environment. The Red Sox should definitely make one final push to strike a deal with Chicago.
2. Anthony Santander can provide Red Sox with plenty of pop
If the Red Sox are in the market for a power-hitting, right-handed outfielder, Anthony Santander is an excellent option. While he’s technically a switch hitter, his ability to hit from both sides of the plate provides built-in flexibility for matchups. At 30 years old, Santander shares some similarities with Teoscar Hernandez, but he’s a few years younger and comes from a division rival, offering the added bonus of potentially weakening the Baltimore Orioles while strengthening Boston’s lineup.
Santander had a breakout season in 2024, finishing with 44 home runs, 102 RBIs, and an .814 OPS for the second-place Orioles. As a veteran presence in a young lineup, he helped stabilize the offense, earning his first All-Star selection. He appeared in 155 games and performed well against the Red Sox specifically, batting .256 with 11 hits, three home runs, and seven RBIs across 11 games. The Red Sox are very familiar with his abilities.
That said, there are some valid concerns about Santander’s performance. His slugging numbers from last season were exceptional, but they don’t fully reflect his past production, with his only comparable season coming in the COVID-shortened 2020 campaign. Additionally, he’s not known for his defense in right field, meaning the Red Sox would be investing mainly in his bat — a bat that may not sustain its 2024 levels. His timing in having his best season yet feels almost too perfect.
Despite these questions, Santander is clearly the type of player the Red Sox need. While he struggles a bit more from the right side of the plate compared to the left, he’s still a solid option in a relatively thin free-agent market. If the Red Sox weren’t willing to splurge for top-tier options like Soto or Hernandez, Santander is a logical and attainable outfield upgrade.
1. Alex Bregman would bring winning experience to the Red Sox lineup
The Red Sox are still in the hunt for Alex Bregman, the top remaining infielder on the free-agent market. After nine successful seasons in Houston, the Astros have seemingly moved on from Bregman, making him available to join a new team. Boston offers a chance to compete in a hitter-friendly park, with the added appeal of a storied franchise rich in history.
Although not an outfielder like Teoscar Hernandez, Bregman is a highly skilled third baseman, with the flexibility to transition to second base if needed. Rumors of moving Rafael Devers to first base would become more plausible with Bregman in the fold. He can fit seamlessly into the heart of Boston’s lineup while offering a dependable glove at third base for at least a few more seasons.
At 30 years old, Bregman is still in his prime, even though last season was somewhat below his usual high standards. He finished with 26 home runs, 75 RBIs, and a .768 OPS. When you factor in his two World Series titles and history of postseason success, it’s clear why the Red Sox would be eager to add him to their roster. While Bregman’s price tag could rise following Willy Adames’ $182 million deal in San Francisco, if the Red Sox want to keep up with teams like the Yankees or Dodgers, making this kind of investment is crucial.
Beyond his on-field abilities, Bregman brings veteran leadership and a winning mentality. His experience and championship pedigree could help elevate the Red Sox clubhouse as they aim for a title. That intangible value should play a significant role in discussions about whether Bregman is “worth” the considerable money he’s expected to command.
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