Red Sox's Biggest Free-Agent Mistake to Avoid This Winter

The Boston Red Sox are close to contending, despite the fact that they were bounced from the playoffs for the second straight year by the New York Yankees in the wild-card round.

Unlike this time last year, the Red Sox already have guys lined up for the 2027 campaign, including Adley Rutschman, Willson Contreras, Caleb Durbin and Curtis Mead, among others. Contreras and Durbin really showed Boston fans what they can do in 2026 and are both under team control beyond the 2026 campaign. Rutschman and Mead were both added before the trade deadline and have team control in 2027, at the very least. Mead has team control beyond that. With a full offseason in the organization, these guys could be even better next year.

Mix that with Boston's elite pitching and you have a team that can contend. The Red Sox should look to add more power, but shouldn't get hasty. They have the talent to contend. They can't go out and overreact into giving out a bad deal now. The top offensive free agents heading to the open market are Randy Arozarena, Seiya Suzuki, Jazz Chisholm Jr., Brandon Lowe and Luis Arraez.

Over the last few years, we've seen some pretty massive deals given out. Shohei Ohtani and Juan Soto got $700 million or more. Vladimir Guerrero Jr. got a $500 million extension from the Toronto Blue Jays. Kyle Tucker got $240 million. Alex Bregman got $175 million. Pete Alonso got $155 million. Kyle Schwarber got $150 million, and the list goes on.

What Should Boston Do This Winter?

Seattle Mariners outfielder Randy Arozarena — Sep 27, 2026; Seattle, Washington, USA; left fielder Randy Arozarena (56) takes a swing during an at-bat against the Los Angeles Angels at T-Mobile Park. Mandatory Credit: Stephen Brashear-Imagn Images | IMAGN IMAGES via Reuters Connect

Arozarena is the top offensive free agent heading to the market after slashing .281/.381/.484 with 26 homers, 79 RBIs and 26 stolen bases in 154 games played. He was awesome. But it was also the best season of his career at 31 years old. He'll be 32 years old before the 2027 season begins. Last year, Arozarena batted .238 and in 2024 he batted .219. The 2026 season was great, but what version of him will a team get? The price tag surely will be high with him being the top free agent bat. But if it approaches the numbers Bregman and Alonso got last year, Boston should avoid.

An Arozarena deal will be expensive and if he were to get a five-year deal, it would run through his age-36 season.

Like Arozarena, Suzuki was awesome in 2026. He hit 26 home runs and drove in 86 runs in 143 games played. He racked up 5.1 wins above replacement. The year before, he had 2.6 wins above replacement. He'll also be 32 years old when the 2027 season begins

On the other hand, Chisholm is just 28 years old, but he's likely to be expensive and isn't much of a positional fit for Boston. Lowe is 32 years old and also plays a position Boston is seemingly set at (second base), although his power would play well as a designated hitter. On the bright side with Lowe, he'll likely be cheaper than Arozarena, Suzuki and Chisholm. He'd be someone who would be intriguing to target on a three-year deal, or something like that.

Arraez is awesome, but he just doesn't have the power Boston needs.

At the end of the day, the Red Sox could use more power. The free agent class is weak in general, which could end up leading to higher prices than you'd expect for the top guys available. Last winter, Tucker, Bregman, Schwarber and Alonso all got big deals. If someone like Arozarena or Suzuki were available would they have gotten the same deals as guys like Schwarber and Alonso? Surely not. When the market opens, if those are the types of numbers the top free agents are looking for, Boston should steer clear and look to the trade market to solve the power problem.

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