Welcome to Part 1 of OTM’s 2025 Red Sox postmortem. Today, we kick off the series by looking at our favorite — and least favorite — moments and players of the season. Check back in for further installments covering management, awards, and offseason needs.
What was your favorite moment of the 2025 Red Sox season?
The Red Sox lost the game, but watching Payton Tolle’s debut in Fenway was the first time in a long time that I felt like people really noticed what was going on. This isn’t a prospect who was hyped up as the next big thing for two years before finally
being promoted. He was a kid who came out of nowhere, and there was a legitimate buzz in the stadium before the game. He came out and dominated, but it was a fun night nonetheless.
— Jacob Roy
I suppose when they clinched that playoff position—especially considering the manner in which they did so. The energy was incredible, the excitement was real, and the world was our oyster for that moment and for a few days after. Ah, take me back to when I was a young man, all those days ago….
— Fitzy Mo Peña
It’s very close for me between Wilyer Abreu’s inside-the-parker followed by a grand slam in the same game and Roman Anthony’s silencing home run at Yankee Stadium. Anthony’s probably wins because A) the call was. fantastic, and B) while I was watching the Wilyer Game, a bottle of honey exploded onto the ceiling of my apartment and that really sucked.
— Avery Hamel
Ceddanne “Nuf Cedd” Rafaela’s walkoff home run against the Rays. The most electric feeling at Fenway Park since Papelbon since 2018. Maybe even further back.
— Mike Carlucci
Every Friday night walk-off at Fenway in the green unis. If I had to pick one, it’s Ceddanne Rafaela’s walk-off triple against Detroit on the final weekend of the season to clinch a playoff spot. His head buried on third base was my favorite image of the year. All-in-all, there were five Friday night walk-off wins between June and September, against the Yankees, Rays, Astros, Marlins, and Tigers.
— Bob Osgood
I’m reaching back to May for this one, despite all the thrilling things that came later. To me, nothing was as majestic, exciting, and visually gorgeous as Jarren Duran’s home run in the hail in the first game of the doubleheader against the Orioles.
— Maura McGurk
It’s the Payton Tolle game for me, too. One of the best days of the baseball year is the day that the hot prospect du jour gets called up. We were absolutely loaded with those in 2025, starting right on Opening Day with Kristian Campbell. But Tolle getting the call to go opposite the best pitcher in the world — and then meeting the moment the way he did — was visceral.
What was your least favorite moment of the 2025 Red Sox season?
Probably losing to the Yankees in the Wild Card round. That sucked.
— Jacob Roy
When it ended.
— Fitzy Mo Peña
Probably that five-game losing streak after they called up Marcelo Mayer. That was really not fun. Also that was like two weeks post-grad for me, so I was kind of going through it at the time.
— Avery Hamel
Payton Tolle being relieved by Greg Weissert.
—Mike Carlucci
Trading Rafael Devers, in the midst of a six-game win streak, moments after completing a three-game sweep of the Yankees at an electric Fenway Park, on Father’s Day. That sounds like a Mad Lib it’s so preposterous.
—Bob Osgood
Wild Card Series, Game 3.
—Maura McGurk
Who was your favorite Red Sox player in 2025?
Garrett Crochet made me feel warm and fuzzy inside every five days or so. It’s been a while since we’ve had scheduled wins based on the starting pitcher.
— Jacob Roy
I concur with Jacob. Oink oink.
— Fitzy Mo Peña
Probably Trevor Story. Crochet was an absolute joy to watch and definitely Boston’s MVP, but Story’s resurgence (and his singlehandedly trying to get the Red Sox a win in Game 2 of the Wild Card), was a beautiful thing to watch and an especially emotional development for me personally. Now please don’t leave us, Trevor.
— Avery Hamel
Roman Anthony.
—Mike Carlucci
Roman Anthony. There’s a decent chance that will be my answer for the next nine years, as well.
—Bob Osgood
I’m almost neck-and-neck with Crochet and Anthony…but if I were getting a jersey tomorrow, it’d be Anthony’s.
—Maura McGurk
Who was your least favorite Red Sox player in 2025?
Even when Walker Buehler had some snazzy box scores, I wasn’t really buying it. I don’t know who is actually in charge of his game plans, but he went out nearly every start and threw seven different pitch types. I wish he had tried to focus on three or four of his best, rather than going for the kitchen sink method. He couldn’t throw strikes, and it was frustrating to watch.
— Jacob Roy
— Fitzy Mo Peña
I’m not quite sure if Jordan Hicks necessarily counts as a “player” this season, so I’ll go with Jarren Duran. For whatever reason, I have a special disdain in my heart for Jarren Duran. And I love to argue with people about it.
— Avery Hamel
It feels unfair to say Dustin May because he didn’t choose to be put into this situation but nevertheless his time was torturous.
—Mike Carlucci
Jordan Hicks, Kyle Harrison, and Dustin May, the three returns in the Rafael Devers deal, with James Tibbs III making a brief appearance before being flipped for May. We’ll leave Jose Bello out of this; he’s just a kid.
At least they aren’t being paid much beyond this year, with Devers’ contract off the books. Pardon me, I’m being told that Jordan Hicks and his 6.95 ERA in 67 1/3 innings will make $12.5 million each of the next two years.
—Bob Osgood
Connor Wong and David Hamilton both wore out their welcome with me this season.
—Maura McGurk
In 10 years, the 2025 Red Sox season will be remembered as…
The year that Roman Anthony arrived. He’s the most important person in New England for the next decade.
—Dan Secatore
The year the Red Sox won the World Series. Wait. Shit. It’s the year that Red Sox baseball was revived in New England. People care again, and that’s a wonderful thing.
— Jacob Roy
The year that got the Red Sox back in the mix for the foreseeable future. Hopefully, we remember it as our equivalent of the 2015 Houston Astros season: one that sets the stage for a generational run of success. I could do without the generational scandal in 2030, though…
— Fitzy Mo Peña
This season felt very 2017-y to me, which, in the long term, is a genuinely good thing! The young superstar debuts in July and gives some life to a generally good team that just loses steam down the stretch. Their early playoff exit was inevitable, but hey, that one win was fun! This will be remembered as not necessarily a new dynasty, but a new core — and hopefully one that’ll stick around for longer than two years after winning a World Series.
— Avery Hamel
Nomar Garciaparra’s callup was in August 1996. Roman Anthony in June 2025. The Red Sox dipped to 4th place in his second year and then ran off six second-place finishes in the AL East. Like Dan said, this is just the beginning.
—Mike Carlucci
The beginning of a new, more successful chapter. It’s going to be fun!
—Maura McGurk
