The Boston Red Sox have done a good job of augmenting their roster this offseason, bringing in a trio of starting pitchers and Willson Contreras to fill some of the largest holes on the depth chart.
Of course, to add talent, you also need to give away talent. That's especially true in trades, but as the Red Sox focus their efforts and resources on marquee free agents, they've also allowed a few key role players to walk away.
So, let's discuss. Which three players that the Red Sox have lost this winter (by any means) will come back to bite them in 2026 and beyond? As a promise to you all — as well as a desire to avoid the most obvious possible answer — don't expect to find Alex Bregman mentioned anywhere below. We've been hurt enough as it is.
3 former Red Sox players who will thrive outside of Boston in 2026
Rob Refsnyder
Perhaps the hardest goodbye Sox fans have had to say this offseason, Refsnyder was a Beantown fixture for the past four seasons. He was a beloved clubhouse presence who also brilliantly filled his niche role as a lefty masher (he had a 159 wRC+ versus southpaws last season).
Now playing for a fellow American League contender in the Seattle Mariners, Refsnyder could wreak havoc on Boston's lefty-heavy pitching staff led by Garrett Crochet and Ranger Suárez. Even when they don't play each other, the veteran outfielder endearing himself to another fanbase will be hard to watch.
Still, it's impossible not to root for him. Hopefully, the Red Sox can avoid the Mariners in the playoffs, lest Refsnyder hit a clutch home run over the Green Monster for the opposition.
Steven Matz
Matz was a sneaky-effective trade deadline addition to the bullpen in 2025, pitching to the tune of a 2.08 ERA while walking just 2.4% of hitters while in Boston. The advanced metrics didn't love him (he was worth -0.1 fWAR), but he got results despite wonky peripherals.
There was hope that Matz, 34, would stick around in free agency, but the division rival Tampa Bay Rays came calling with a multi-year offer that the veteran southpaw couldn't refuse. Interestingly, he'll actually try to convert back to the rotation after pitching out of the bullpen for the past few seasons, which could make his new contract even more of a bargain if it works out.
The real reason this loss stings is that the Red Sox have also lost Brennan Bernardino, Chris Murphy, and (potentially) Justin Wilson this offseason, leaving Jovani Morán as the lone lefty in the bullpen outside of closer Aroldis Chapman. Having Matz, even in a glorified LOOGY role, would have calmed a lot of nerves late in games.
Jhostynxon Garcia
Garcia was the main casualty of a high-risk, high-reward trade that landed starting pitcher Johan Oviedo in Boston. Known as "The Password" for his hard to spell first name, the top prospect could make the trade look silly in a few years if he breaks out with the Pittsburgh Pirates.
His track record is impressive, having hit .267/.340/.470 with 21 home runs and a 116 wRC+ in the minors in 2025. He was even better in 2024, hitting 23 bombs and producing a ridiculous 149 wRC+. There's a good chance he settles in as a middle-of-the-order slugger in the big leagues somewhere down the line.
Of course, this deal made sense at the time given the team's roster construction (i.e., a lack of starting pitching and a glut of outfielders), and Oviedo could make this deal look lopsided for the Sox if he experiences his breakout. But even if that happens, it still won't feel good to watch Garcia emerge into an annual 30-homer threat in Pittsburgh.