🚨EXCLUSIVE: Ranking the 5 Departed Red Sox Players Boston Will Miss the Most—Heartbreaking Farewells that Leave Fans in Tears. From legends to fan favorites, who left the biggest void? The emotional impact of their departures will echo throughout the season...

It was an offseason of transformation for the Boston Red Sox, and not all of it was exciting news.

The Red Sox lost some real talent this offseason, including the player that most would agree was the top dog in terms of leadership last year. That same player has never missed the playoffs in his career, while the Red Sox are hoping to prove their first appearance in four years wasn’t a blip on the radar.

Which players are the Red Sox most likely to think to themselves, “Man, wish he was still here” this year? Below, we’ve attempted to rank them in order.

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1. Alex Bregman

Mar 24, 2026; Mesa, Arizona, USA; Chicago Cubs third baseman Alex Bregman hits a home run against the New York Yankees during spring training at Sloan Park. Mandatory Credit: Mark J. Rebilas-Imagn Images | Mark J. Rebilas-Imagn Images

Bregman has no close second here. He was worth 3.5 fWAR in 114 games and made his third career All-Star team, but he was worth just as much to other players’ success. The Chicago Cubs knew they were getting a good one when they pulled off January’s free agency heist.

The Red Sox certainly hope Caleb Durbin can perform at or above the level he achieved for his last few months with the Milwaukee Brewers, but matching Bregman’s combination of performance and leadership is pretty unfathomable.

2. Kyle Harrison

Milwaukee Brewers pitcher Kyle Harrison throws in the outfield during spring training workouts Monday, February 16, 2026, at American Family Fields of Phoenix in Phoenix, Arizona. | Dave Kallmann / Milwaukee Journal Sentinel / USA TODAY NETWORK via Imagn Images

Speaking of Durbin, Red Sox fans already know to be terrified by what the Milwaukee Brewers will do with Harrison. He was set up to be perhaps the No. 9 option on Boston’s starting pitching depth chart, but he’s got a revamped change-up, and no one should be surprised if he puts up 25-plus starts and a low-threes ERA in Milwaukee.

3. Rob Refsnyder

More leadership out the door, and though Refsnyder played a lot less than Bregman, he could carry the offense on any given night if there was a left-handed pitcher on the mound. Plus, his lefty-killing protege Romy Gonzalez is on the 60-day injured list.

4. Lucas Giolito

Sep 6, 2025; Phoenix, Arizona, USA; Boston Red Sox pitcher Lucas Giolito (54) celebrates after Boston Red Sox outfielder Ceddanne Rafaela (3) robs a home run during the fifth inning against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Arianna Grainey-Imagn Images | Arianna Grainey-Imagn Images

Giolito arguably could have been ranked as high as second on the list, but that would be more applicable if we were counting on him repeating a 10-win, 2-WAR season. Most metrics expect him to regress, and the fact that no team has signed him yet probably means most front offices expect the same.

5. Steven Matz

Feb 23, 2026; Phoenix, Arizona, USA; Seattle Mariners outfielder Rob Refsnyder against the Los Angeles Dodgers during a spring training game at Camelback Ranch-Glendale. Mandatory Credit: Mark J. Rebilas-Imagn Images — Feb 26, 2026; Fort Myers, Florida, USA; Tampa Bay Rays pitcher Steven Matz (32) throws a pitch in the first inning against the Boston Red Sox at JetBlue Park at Fenway South. Mandatory Credit: Jim Rassol-Imagn Images | Jim Rassol-Imagn Images

Any time the Tampa Bay Rays sign a pitcher in free agency, we’ve got to have our guard up. And the fact that Matz went to a team in the division means it will be all the more annoying if he toes the slab against the Red Sox and looks untouchable.