Red Sox 2026 Offseason Guide on Free Agents, Trade Targets, More Roster Moves After Wild Card Loss

After the New York Yankees swept the Wild Card Series, the Boston Red Sox are still waiting for their first World Series since 2018. On the plus side, they turned nothing into something in 2026.

The season could not have started with worse vibes. It wasn't just the sacking of Alex Cora and several of his top lieutenants. It was also the ugly baseball that, at one point, resulted in a record of 14 games under .500.

That the Red Sox finished with a 55-29 run to earn a second straight postseason ticket is a miracle, especially without Garrett Crochet and largely without Roman Anthony. That couldn't have happened without the roster's extraordinary depth, headlined by four All-Stars: Willson Contreras, Ceddanne Rafaela, Ranger Suárez, and Aroldis Chapman.

The victory lap belongs to Chad Tracy for being just what the team needed in the manager's chair, and to chief baseball officer Craig Breslow for proving he does, in fact, know how to build a roster. He's the one responsible for Contreras, Suárez and Chapman, as well as Sonny Gray, Caleb Durbin and Payton Tolle.

All told, the Red Sox look like a team on the verge of taking the next step. Let's look at how that could happen by taking a comprehensive look at their offseason outlook.

The Red Sox signed IKF to a one-year, $6 million deal last winter, but he played only 66 games because of a stress fracture in his left forearm. He was sidelined for more than two months, from June 18 to September 1.

When he was healthy, he provided his usual blend of versatile defense and contact-oriented offense. The end result was 1.6 rWAR, more than he produced across 138 games with two teams in 2025.

The experience could leave the Red Sox open to bringing the 31-year-old back for 2027, but they could just as easily stick with other incumbents. Nick Sogard, Andruw Monasterio and Anthony Seigler can do what IKF does, and for less money.

The Red Sox signed Sandoval to a two-year, $18.25 million deal back in December of 2024. He was recovering from Tommy John surgery at the time, and he was ultimately unable to return before the end of 2025.

By the time Sandoval suited up for Boston on July 9 this year, it had been more than two years since his last major league appearance. He never really found a groove, posting a 5.12 ERA over 70.1 innings.

The Red Sox probably won't rush to bring the 29-year-old lefty back for another go in 2027. Even without him, they're flush with left-handed starters.

LHP Aroldis Chapman: Triggered 1-year, $13 million vesting option

This doesn't seem as widely known as it should be, so just in case: Chapman will be back in the Red Sox bullpen in 2027.

The nine-time All-Star triggered his 2027 option when he crossed the 40-inning threshold in mid-August. He's having a heck of a late-career surge in Boston, making 120 appearances and posting a 1.51 ERA since the start of 2024.

RHP Sonny Gray: 1-year, $30 million mutual option

Here's where it gets interesting: it depends on whether the 36-year-old Gray wants to keep pitching.

According to Alex Speier of The Boston Globe , Gray is willing to retire "in a heartbeat" if his family wants him to. Some in the Red Sox organization are apparently taking that seriously, and they should. Gray has 14 years in the majors and his career earnings are already past $100 million.

If Gray wants to keep pitching, he'll likely turn down his side of the $30 million mutual option. After going 18-5 with a 2.72 ERA over 169.0 innings, he could be worth more than that on an open market with precious few impact free agents.

RHP Garrett Whitlock: 1-year, $8.25 million club option

Over the last two seasons, Whitlock has appeared in 116 games and put up a 2.03 ERA over 124.1 innings. That's with a 2.15 FIP and 4.55 K/BB ratio.

This means picking up Whit lock's option for next year is a no-brainer for the Red Sox, even if his stint on the IL this year for elbow inflammation raised questions about his durability.

After starting the year with Double-A Portland, Arias moved so quickly and so emphatically throughout 2026 that he was knocking on the door of the majors by September.

All told, he had a .957 OPS and 25 home runs in 117 games between Double-A and Triple-A. As a plus defender at shortstop, the Red Sox have every reason to be hyped for his arrival.

Even though the Red Sox decided not to call up Arias in September, whether the 20-year-old cracks their 2027 Opening Day roster will be a storyline in spring training. Trevor Story should consider himself on notice.

Gonzales only has 18 games with Portland under his belt, so he's likely more of a late-2027 candidate for a call-up. Even that would be aggressive, since he won't turn 20 until New Year's Eve at the end of 2026.

It doesn't hurt Gonzales' case that he's a right-handed hitter, as Boston could use more thump from that side of the dish. He blossomed as an all-around bat this year, posting a .834 OPS with 19 homers over 107 total games in the minors.

Godbout's 2026 season took an unfortunate turn in late May, when he dislocated his left shoulder and needed surgery . He didn't return until July 31.

Still, he needed just 61 games to see action at three levels of the minors, culminating in a 22-game stay with Portland. He posted a .402 OBP in the process, with more power than expected. If he keeps hitting, the 22-year-old could position himself for major league action at shortstop or second base next season.

Rankings according to B/R's Joel Reuter .

The Red Sox only hit 163 home runs this season, ranking fifth from the bottom of MLB. While 21 different players hit at least one home run, only Willson Contreras (27) and Wilyer Abreu (24) stood out as especially dangerous.

The cleanest fit is a slugger who can play left field and/or DH. Ideally, the new guy would also hit right-handed. Good righty power is scarce across MLB, and the Green Monster always beckons for hitters with pop to left field.

This is a bit of a hedge, as the assumption here is that the Red Sox can't count on having Sonny Gray back in 2027. Even if he doesn't retire, teams almost never exercise mutual options.

Without Gray, the Red Sox will still have Garrett Crochet, Payton Tolle, Ranger Suárez and Jake Bennett, with Brayan Bello, Johan Oviedo or Kutter Crawford to round things out. It's not a bad bunch, but it would indeed look lacking without a Cy Young-caliber righty at the top or in the middle.

It just feels like it's time for the Red Sox and Duran to break up, doesn't it? He's been a regular in trade rumors for two years, and the energy he brings to the team isn't always positive.

Speculation about Duran finally leaving Boston has already begun, with Mark Feinsand of MLB.com rating him as a top offseason trade candidate in September. The Red Sox can market him as an All-Star outfielder with two years of club control before free agency.

Arozarena will turn 32 on February 28, and he'll be tied to draft-pick compensation after rejecting a qualifying offer from the Mariners. Whoever signs him will find it costly and risky.

All the same, the Red Sox are among the 2021 AL Rookie of the Year's best fits on paper. He's a right-handed hitter who churns out 20-20 seasons like clockwork, and Fenway Park could push his power output closer to 30 homers annually.

Wilyer Abreu is one of the best right fielders in baseball, so Suzuki would need to be open to left field for this to make sense for Boston. He's only started 15 games on that side of the grass, which has been Ian Happ's domain in Chicago.

Whatever the case, Suzuki's bat plays. The 32-year-old has a 128 OPS+ in five major league seasons, with a baseline of 20 home runs. He's also a slightly more pull-power righty hitter than Arozarena, with a 20.9 Pull-AIR% this year.

If Gray retires, the Red Sox can't do anything about it. If he decides to keep pitching but declines his mutual option, the chase to keep him should be on.

This was too good of a partnership to end after one year, and the organization owes the fans one after losing Alex Bregman under similar circumstances. In this case, that might be worth even $35 or $40 million in a one-year deal.

The Red Sox must have a Plan B if Gray retires or walks, and King should be the guy if he opts out of a three-year, $75 million deal with San Diego.

The 31-year-old was on Boston's radar last offseason before he returned to the Padres. He's a Boston College alum who has topped 4 rWAR in two of the last three seasons, most recently with a 3.21 ERA over 185.0 innings this year.

Before they landed Adley Rutschman on deadline day, Sean McAdam of MassLive reported that the Red Sox made a run at De La Cruz that culminated in an actual offer. Obviously, nothing came of that.

It's worth trying again, even if the Red Sox would presumably have to be ready to surrender Payton Tolle or Franklin Arias. De La Cruz reestablished himself as a budding superstar in 2026, going off for a 30-30 season and 5.6 rWAR. He's still only 24, and under club control through 2029.

This is another oldie-but-goodie trade concept. The Red Sox were in on Ryan during the summer of 2025, when they reportedly made an offer of Tolle and Arias for him.

That particular ship has presumably sailed for the Twins, and they say they're looking to contend in 2027 anyway. Yet Ryan still has the stuff/command profile that fits the Craig Breslow model, so the 30-year-old should be another Plan B if Sonny Gray moves on this winter.

There was some smoke on the Red Sox making a move when the D-backs were shopping Marte last winter. Nothing came together, and it's arguably a dodged bullet all these months later.

That said, the Red Sox can't turn their backs if Arizona puts Marte on the market again this winter. Even if his clubhouse presence is a question mark, the 32-year-old is a proven superstar talent who is on a relatively team-friendly contract. He's owed just $76 million through 2030.

The fit between Arozarena and the Red Sox is just too good, and the appetite to spend on a slugger should be there. He's the missing piece this team needs to be able to chart a straight path to the World Series.

There's otherwise not much change to see here, though some might be disappointed that Franklin Arias is not projected as the starter at shortstop. That really does feel like a 50-50 thing, though our thinking is that Boston will roll with a Contreras-Mead-Story-Durbin infield until an injury messes with the plan.

Honestly? This is presented with maybe a 25 percent confidence level. It does look like a Franken-bench.

Assuming Gasper is recovered from biceps surgery in time for spring training, Yoshida and Campbell are the question marks here. Our thinking is that Campbell can earn a job next spring, while Yoshida is still worth keeping around for his quality at-bats even if he's not worth his $18.6 million salary.

No Sonny Gray? No Sonny Gray. If it's between spending on Arozarena and spending on Gray, the Red Sox should lean toward the area that's not a strength. Plus, Arozarena is surely going to come cheaper.

It's still a solid rotation even without Gray. Tolle, Suárez and Bennett all posted ERAs in the 3.00s this year, and at least one of them (i.e., Tolle) has further upside. If healthy, Crochet is one of the five best pitchers in the sport.

If you're wondering where Estrada is coming from, we like the idea of swap of him for Jarren Duran as a fun challenge trade between Boston and San Diego. The Padres have been reported to covet Duran in the past.

It's a familiar group otherwise, with maybe the only real surprise being that we're sticking with Bello in long man/swingman role. It suited him after he returned from a minor league banishment in July, resulting in a 2.11 ERA over 55.1 innings.

Stats courtesy of Baseball Reference , FanGraphs and Baseball Savant .