Red Sox's Biggest Winners, Losers From Rollercoaster 2026 Season

Sep 29, 2026; Bronx, New York, USA; Boston Red Sox starting pitcher Payton Tolle (70) pitches against the New York Yankees during the second inning of game one of the Wildcard round of the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images IMAGN IMAGES via Reuters Connect

Red Sox's Biggest Winners, Losers From Rollercoaster 2026 Season

Originally posted on Boston Red Sox on SI
By Patrick McAvoy | Last updated Oct 8, 2026 4:57 PM ET

Add us as a preferred source on Google

The dust has started to settle on the 2026 Major League Baseball season for the Boston Red Sox and now is a perfect time to look back, before we are too far removed and thinking ahead to 2027.

In Boston, it's not necessarily enough to just get to the playoffs. But even with that being said, credit has to be given to this club for putting together the best mid-season turnaround in franchise history. Plus, the turnaround didn't just help the 2026 season. If Boston didn't turn its season around, Adley Rutschman and Curtis Mead wouldn't be on the team right now. Also, a few pieces, like Willson Contreras perhaps, would've been traded. The mid-season turnaround allowed the club to add, not subtract, to try to make a run in 2026 and better prepare for 2027. That's a success.

There's work to do. But it was a fun season. With that being said, let's take a look at the biggest winners — and losers — from the Red Sox in 2026.

Winners

Payton Tolle

There are few players more beloved on the Red Sox's roster than Tolle, and he has the talent to match. Tolle didn't make the Opening Day roster but was quickly promoted. He had a 3.03 ERA in his rookie season and started Game 1 in the playoffs. He's an ace in the making.

Sonny Gray

Gray was acquired to be Boston's No. 2 starter and he turned out to be the ace of the staff. Garrett Crochet was on the shelf and Gray stepped up and had one of the finest seasons of his career. Gray logged a 2.72 ERA in 29 starts and absolutely should've been an All-Star.

Willson Contreras

Willson Contreras was a leader for the 2026 Red Sox and also set a new career high with 27 home runs and a .901 OPS. A truly awesome season for the slugger.

Ceddanne Rafaela

Rafaela earned the first All-Star nod of his career and should have another Gold Glove coming his way. In 2026, his bat started to catch up to his glove.

Caleb Durbin

Few players represent the 2026 Red Sox better than Caleb Durbin. This is a guy who struggled out of the gate to the point that some fans questioned whether he should even be in the lineup. Then, he got hot and quickly became a fan favorite in the Boston fanbase.

Losers

Roman Anthony

Anthony is on this list simply because he was unlucky and missed most of the season due to injury. It was a lost season for the young outfielder.

Garrett Crochet

The same can be said about Crochet. He returned in the playoffs, which is a good sign for a healthy offseason.

Trevor Story

Injuries derailed Story's season as well. Fortunately, he looked great down the stretch and is healthy now.

Jarren Duran

Duran hit for solid power, but his bat in general struggled. He finished the season batting .207.

While Boston didn't accomplish all of its goals, the 2026 Red Sox gave the fanbase a lot to be excited about throughout the campaign, and for the future. It's no secret that the first few months of the season were a wreck. The Red Sox started off on a bad note, fired Alex Cora and a handful of coaches and then had to pick themselves up and get back in the race after putting themselves in a bad position in the first place. At 32-46, the Red Sox were talked about as potentially one of the biggest sellers in the league for the 2026 trade deadline. Boston turned it around, though, and delivered a historic summer that culminated in a playoff appearance.

This article first appeared on Boston Red Sox on SI and was syndicated with permission.

More must-reads: