The Boston Red Sox enter the offseason with a lot of work to do, particularly on offense, as they look to build a World Series contender in 2027. With so many pieces from the 2026 roster under team control, Chief Baseball Officer Craig Breslow will likely have to move some major league pieces in offseason trades. Deciding who is going to be a crucial piece moving forward and who might be better served as a trade chip. 

Here’s who the Red Sox should consider untouchable in trade discussions for one reason or another: 

Heading into the 2025 offseason, this list would have likely been a lot longer. However, after injuries kept Garrett Crochet and Roman Anthony out for most of the regular season, the Red Sox have only one player who should be considered totally untouchable in most trade discussions. 

No surprises here: the 23-year-old left-hander is the Red Sox's most untouchable player heading into the offseason. In 26 starts, Tolle posted a 3.03 ERA, ranking in the top five among all rookie starters in ERA (4th), strikeouts per nine innings (10.35, 2nd), walks per nine (2.42, 7th), FIP (3.04, 1st), and fWAR (4.1, 2nd).

After starting for the Red Sox in Game 1 of the Wild Card series against the New York Yankees, Tolle looks like an ace in the making, poised to anchor the Boston rotation alongside Crochet for years to come. 

Surely every player in the league has a price; any head of baseball operations who says otherwise would be doing their organization a disservice. But after a rookie campaign that should see him finish top three in American League Rookie of the Year voting, Tolle’s should be astronomical. 

Entering the regular season, no players were more important to the Red Sox's success than Crochet and Anthony. In a stroke of bad luck, both players missed the majority of the regular season with injuries. While it's incredibly unlucky that either player would be a trade candidate if they hadn't gotten hurt, their value is likely far too low now for Breslow to even entertain offers. 

The 2025 runner-up to the American League Cy Young Award, Crochet got off to a rough start to the 2026 season, posting a 6.30 ERA in three starts before left shoulder inflammation and a LAT strain landed him on the injured list on April 26 and ended his regular season. 

The 27-year-old returned for one relief appearance in Game 2 of the Wild Card series against the Yankees, allowing four earned runs on three hits and striking out one batter (runner reached on a dropped third strike) without recording an out. 

The good news is that Crochet enters the offseason in full health and figures to return to the top of the Red Sox rotation. 

The 22-year-old outfielder is one season removed from being the top prospect in baseball, drawing comparisons to a young Juan Soto. Under pressure to carry the Red Sox offense, Anthony struggled to start the season before tearing a ligament in his right ring finger on May 4. After missing 101 regular-season games, Anthony returned to the lineup on Aug. 30, hitting .262/.321/.476/.797 in 25 games over the last month of the season. 

However, his return was short-lived; he was removed from Game 1 of the Wild Card round after aggravating his ring finger injury again, and additional imaging revealed new areas of concern in his hand and wrist, causing the team to remove him from the postseason roster.

Overall, Anthony hit .245/.339/.396/.735 with five home runs, 11 doubles, and three triples, driving in 15 runs in 55 games. Despite the results that don't jump off the page, Anthony showed plenty that signaled a breakout was on the horizon, had he not missed so much time. 

While these players aren’t necessarily “untouchable” because they’re key pieces moving forward (although one is), any trade involving them would have to be approved one way or another. 

After waiving his no-trade clause with the St. Louis Cardinals to approve a deal to Boston last offseason, the All-Star first baseman retains a 10-team no-trade list heading into the 2027 and 2028 seasons. 

The 34-year-old posted one of the best seasons of his career in his first year in Boston, hitting .275/.386/.516/.901 with career highs in home runs (27), RBI (81), on-base percentage, and OPS en route to the third All-Star appearance of his career. 

Contreras finished the season top three in the sport in both OPS (3rd) and weighted runs created plus (151, T-3rd), trailing only the likely winners of both MVP awards, Houston Astros designated hitter Yordan Alvarez and Chicago Cubs center fielder Pete Crow-Armstrong. 

With an offense desperate for more pop, it would be shocking to see Breslow trade his All-Star first baseman. 

The 33-year-old shortstop wasn’t given a no-trade clause when he signed a six-year, $140-million deal with Boston ahead of the 2022 season. However, he has earned 10-5 rights, with 10 or more years of Major League service time and five consecutive years with the same team, which grant him a full no-trade clause. 

It was already going to be tough for Breslow to trade Story, as he once again missed substantial time with injury for the fourth time in five seasons with the Red Sox. Story has also wildly underperformed in all but the 2025 season, hitting .245/.296/.404/.701 in 384 games in a Red Sox uniform. 

With top prospect Franklin Arias knocking on the door to the big leagues and the team reportedly pursuing a “long-term solution” at shortstop ahead of the trade deadline. It’s entirely possible that Story has played his last game in a Red Sox uniform. But he’ll have a say in where he goes, whether that be in the trade market or if he’s designated for assignment. 

How the Red Sox approach the offseason ahead of the seemingly imminent lockout is the No. 1 storyline to follow over the next month. 

With the Red Sox officially in offseason mode, Zach Coe and David Azer are back on the 'Entering Kenmore' Podcast discussing how close Boston is to winning a World Series, offseason needs, and whether or not the 2026 season was successful. Check it out wherever you get your podcasts, or in the YouTube player below: