It has been a productive offseason for Craig Breslow and the Boston Red Sox, who are operating with more aggression than we’re used to seeing. Garrett Crochet and Walker Buehler should revive an ailing rotation and put Boston squarely in the postseason race, despite the overwhelming quality of competition in the AL East.

That said, most of the questions surrounding this Red Sox team are of the “what if” variety. The Red Sox are spending, sure, but whiffing on Juan Soto, Max Fried and now Teoscar Hernandez feels like a failure, even if the team has improved.

The latter was heavily connected to Boston in the weeks leading up to his decision to re-sign with the Los Angeles Dodgers. Soto and, to a certain extent, even Fried felt like pipe dreams, but Hernandez was squarely in Boston’s price range. He was also a perfect fit, offering the right-handed power Boston’s lefty-dominated lineup so starkly lacks.

In the end, however, $66 million over three years was enough for Hernandez to stick with the reigning champs. More than $23 million is deferred, and there’s a $15 million option for a fourth year.

That leaves Boston grasping at straws as the free-agent pool dwindles. Here are a few viable backup plans that Breslow ought to pursue.

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We’ve already seen Breslow and Chris Getz strike up one blockbuster trade this winter, so why not another? The Red Sox are loaded with top prospects and eager to contend. The Chicago White Sox are coming off of a historically bad season and desperate to restock the farm system. Luis Robert Jr. feels like the logical next target for Boston.

The Red Sox, again, need a prominent right-handed bat to balance out their lineup. Robert can fit the bill. He struggled last season, slashing .224/.278/.379 with 14 home runs and 23 stolen bases in 100 games, but we shouldn’t take those numbers at face value. Robert was dealing with a lingering hip injury and never quite looked himself.

We should instead harken back to 2023, when Robert posted an .857 OPS — a full 200 points better than in 2024 — with 38 home runs and 20 stolen bases. That landed him 12th in AL MVP voting. At just 27 years old, Robert is still, theoretically, on the upswing. If he can get healthy and get back into a rhythm, the Red Sox could have their cleanup man of the future. His contract includes affordable $20 million club options for 2026 and 2027, so Boston can plan on three full years of Robert’s contributions.

The combination of age, contract and upside here is hard to come by. There is risk, sure, but Robert is due for a bounce back. It ought to come easier if he’s in a winning situation. The Red Sox should absolutely poke around Chicago one last time.

2. Anthony Santander can provide Red Sox with plenty of pop

If the Red Sox want a home run-hitting, right-handed outfielder, look no further than Anthony Santander. He’s actually a switch hitter, so there’s baked-in matchup flexibility. The 30-year-old shares a few exciting parallels to Hernandez, but he’s also a few years younger and coming from Boston’s own division. This is a chance to screw over the Baltimore Orioles, who effectively replaced Santander with former Boston slugger Tyler O’Neill. This is poetic.

Santander finished last season with 44 home runs and 102 RBI on an .814 OPS for the second-place O’s. He was the veteran stabilizer in the middle of a young lineup, providing Baltimore with a consistent source of runs and earning his first All-Star berth in the process. He appeared in 155 games and performed well against Boston specifically, batting .256 with 11 hits, three home runs, and seven RBI across 11 head-to-head appearances. The Red Sox are intimately familiar with what Santander brings to the table.

It’s more than fair to wonder how sustainable Santander’s slugging is. He hasn’t posted comparable numbers outside of the COVID-shortened 2020 season. He isn’t much of a defender out in right field either, so the Red Sox are investing almost exclusively for Santander’s bat, which could wane in value. He picked the absolute perfect time for his best season. It almost feels a little too perfect.

Despite those concerns, however, Santander is plainly what the Red Sox are looking for. He does struggle a bit from the right side of the plate, compared to the left, so it’s not an ideal fit. But, the remaining free agent pool is short on “perfect” options. If the Red Sox weren’t going to splurge enough for Soto or Hernandez, Santander was always the logical outfield upgrade.

The Red Sox are still in the mix for Alex Bregman, the best remaining infielder on the free-agent marketplace. After nine successful years in Houston, the Astros have effectively cast Bregman aside. He’s going to a new team, it’s just a question of where and when. The Red Sox offer a chance to contend in a hitter-friendly ballpark, not to mention decades of unique organizational history.

He’s not an outfielder, like Hernandez, but Bregman is a talented defender at third base, with enough flexibility to transition to second base if needed. There has been talk of moving Rafael Devers to first, which becomes an even easier decision if Bregman signs on. The Red Sox can comfortably plug Bregman into the heart of the lineup while trusting that his glove will hold up at an above-average level for at least a few more years.

At 30 years old, Bregman is presumably still in his prime. Last season was not great by his lofty standards, but Bregman posted 26 home runs and 75 RBI to go along with his .768 OPS. Factor in two World Series rings and a long track record of October excellence, and it’s easy to see why the Red Sox would fall in love. There’s a good chance that Bregman runs up his price after Willy Adames’ $182 million contract in San Francisco, but if the Red Sox want to keep pace with the Yankees or, ultimately, the Dodgers, this sort of expense is necessary.

More than a solid two-way presence on the field, Bregman is the sort of veteran leader who can take root in Boston’s clubhouse and elevate the entire unit. The Red Sox are trying to reach the mountaintop, and Bregman knows how to get there. That should factor into debates about whether or not Bregman is “worth” the money he’s about to receive.