Boston Red Sox fans got the pleasure of seeing the New York Yankees get swept in the ALDS, but they first had to suffer a brutal loss in the Wild Card round.
Boston's front office has much to think about after an embarrassing 18-2 aggregate loss to the Yankees. It was the second straight year that Boston has bowed out to its archrival. The Yankees have arguably regained big brother status in the rivalry, but at least they don't get far after beating Boston gives them all kinds of unwarranted confidence.
The mission for Craig Breslow and Boston's brass is to rebalance the scale and prevent the Yankees from dominating in the coming years. There's also the AL East-winning Tampa Bay Rays, who were New York's undoing, to deal with.
Breslow's been aggressive when it comes to acquiring new talent, and he'll need to remain so this winter. There'll be trades to make, but the free agent market will also be important. Here are three free agents the Red Sox should target.
3 free agents the Red Sox must target to get back to beating the Yankees in the playoffs
Brandon Lowe
It's about time the Red Sox fully sort out the situation at second base. Boston went with Marcelo Mayer there for much of 2026, but that didn't end happily. Curtis Mead is good enough to start at second in 2027 (he'd better be, seeing as the Red Sox gave up Connelly Early to get him!), but Mead can also play virtually every infield position. Acquiring a superior second baseman would allow Boston to use Mead as a super utility guy. And that's exactly what they should plan for in targeting Brandon Lowe.
3️⃣3️⃣ HRs this season for Brandon Lowe!
— Pittsburgh Pirates (@Pirates) September 20, 2026
9️⃣6️⃣ HRs at home this season (! NEW FRANCHISE RECORD!) pic.twitter.com/T9s8DRk95S
Lowe is coming off a monster season; he's still in his prime years at 32, and he has a ridiculous career 1.138 OPS at Fenway Park. The Red Sox need more power in the lineup. They only had two players hit 20-plus homers in 2026 — that's not going to get it done in October. Lowe's capable of hitting 30-plus, especially when playing half of his games at Fenway.
Randy Arozarena
The Red Sox failed to land the best right-handed bats available last offseason (see: Pete Alonso, Alex Bregman). Boston should avoid the same mistake this coming winter by going out and throwing a huge offer at Arozarena, who, by the way, is a playoff riser.
Of course, it's Arozarena's substantial regular-season numbers that are about to get him paid. Most recently, he hit .281/.381/.484 line with 26 homers, 79 RBI, and 26 steals for the Seattle Mariners in 2026. Like Lowe, Arozarena is still in his prime at 31 years old.
The Red Sox would surely have to trade Jarren Duran to make room in their outfield for Arozarena, but you'd have a hard time assembling many (if any) Boston fans who would be vehemently against that decision at this point.
Michael King
The Red Sox may lose Sonny Gray this winter. Either way, Boston should be looking to add another premier starter to guard against inevitable injuries to their best arms. Look what happened to Garrett Crochet in 2026.
King is expected to opt out of his deal with the San Diego Padres and enter free agency, according to top MLB insiders like Jeff Passan. A former Yankee, King would be a nice righty to replace Gray and help offset the higher number of lefties in Boston's rotation.
Continuing the theme here of free agents in their early 30s, King is 31 and has displayed solid durability for the Padres in recent years, making 30-plus starts in two of his last three seasons in San Diego. One of those seasons (2024) saw King finished seventh in National League Cy Young voting. He was very solid in 2026, leading the Padres' staff in innings pitched (185.0) and WAR (4.3).
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