When Will the Boston Red Sox Be Contenders Again?

The Boston Red Sox have been making moves to improve this season. Have they done enough to contend in 2024, or are they still years away?

Triston Casas of the Boston Red Sox celebrates after hitting a solo home run in the top of the fifth inning against the San Francisco Giants at Oracle Park.
SAN FRANCISCO, CALIFORNIA - JULY 28: Triston Casas #36 of the Boston Red Sox celebrates after hitting a solo home run in the top of the fifth inning against the San Francisco Giants at Oracle Park on July 28, 2023 in San Francisco, California. (Photo by Lachlan Cunningham/Getty Images)

After missing the playoffs four of their last five seasons, the situation in Boston seems dire. The Red Sox finished 2023 last place in their division, below .500 and with many questions about the team’s direction for 2024 and beyond.

The Red Sox first offseason move was to bring in Craig Breslow as their new Chief Baseball Officer. Many believed the decision to part ways with Chaim Bloom meant the Red Sox were ready to spend big and catapult their way back to contention. However, their offseason got off to a quiet start as the team passed on many of the big name free agents.

Their first notable player move came in early in December, when the Red Sox sent Alex Verdugo to New York in a rare trade with their division rivals. In exchange, Boston received right-handed pitchers Greg Weissert, Richard Fitts and Nicholas Judice.

The Red Sox then added outfielder Tyler O’Neill via a trade with the Cardinals and reportedly signed free agent pitcher Lucas Giolito. But Boston’s biggest move of the offseason came Saturday, when they sent Chris Sale to Atlanta in exchange for infielder Vaughn Grissom.

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Will these moves be enough to bring the Sox back into the mix for 2024?


Starting pitching was and continues to be the biggest question mark surrounding the 2024 Red Sox. The possible addition of Giolito is interesting, and a bounce back season could definitely be in the cards for him. But, after sending Sale away, the Sox still only have four starting pitchers.

As it stands now, Brayan Bello, Kutter Crawford, Tanner Houck and Giolito make up the starting rotation. Bello was a mixed bag in 2023. There were some major improvements, but he still faces issues of inconsistency. He has the makings to become a solid fixture in the Red Sox rotation, but is probably still a season or two away from being the ace Boston desperately needs.

If the Red Sox are truly interested in contending this season, they must add another starter. Even if they don’t find their ace this offseason, there are still several proven starting pitchers available, and adding any one of them would be a big help.

Looking at the top of the free agent market, signing Jordan Montgomery would go a long way towards pushing the Red Sox towards contention. Montgomery has reportedly been living in Boston this offseason, and could slot in atop the Red Sox rotation next year, while being a long-term answer as more of a No. 2 or 3 once they find their ace.

Shota Imanaga is another free agent option the Red Sox should consider, after striking out on their free agent pursuit of fellow Japanese free agent Yoshinobu Yamamoto. Imanaga would not be the ace that Yamamoto would have been, but he has the potential to be a very solid option moving forward.

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It’s unclear who the fifth Sox starter will be, but one thing that is clear is they can’t continue to shuffle pitchers back-and-forth between the starting rotation and the bullpen. They need to create clear, defined roles for players like Garrett Whitlock and Nick Pivetta.

This past year was a wildly inconsistent for the Red Sox, and a lot that stemmed from their ever-changing pitching staff. Before Spring Training begins, Boston needs to decide who their starting pitchers are, who the relievers are and do their best to stick to it.

Offense and Defense

While the pitching staff seems like more of the same for the time being, the Red Sox have a lot to look forward to in regards to the rest of the team.

Triston Casas is coming off of a breakout season, and other young players like Jarren Duran, Wilyer Abreu and Ceddanne Rafaela showed some really positive signs. Not mention, Masataka Yoshida should begin reaping in the benefits of now having a full MLB season under his belt.

Trading away Verdugo helped clear up Boston’s overcrowded outfield. There is still a chance the Red Sox sell high on Duran, but for now, expect Yoshida, Duran and O’Neill to be the everyday starters, with Abreu and Rafaela as solid options on the bench.

Having more defined roles in the outfield this season will allow Yoshida and Duran to further develop defensively, and if O’Neill stays healthy, the two-time Gold Glove winner should be an excellent complement to the two.

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Also, adding O’Neill gives the Red Sox a much needed right-handed bat. While his offensive numbers have dropped, a healthy O’Neill could look a lot closer to his 2021 self, when he slashed .286/.352/.560 with 34 homers, 80 RBIs and 15 stolen bases.

Looking at the Red Sox infield, they are already in much better shape than last season.

A healthy Trevor Story and the addition of Vaughn Grissom go a long way in cleaning up the middle infield, which was disastrous in 2023. If Casas continues to build upon last season, the Red Sox infield should be running a much smoother operation in 2024.

However, there is still the question of Rafeal Devers. After signing an 11-year extension last season, the superstar slugger obviously isn’t going anywhere. But, after seven seasons in the majors, his defense still leaves something to be desired.

Currently, the Red Sox DH spot is open, and moving Devers into wouldn’t be that shocking of a move. But unless the Red Sox have plans to sign an elite third baseman, there’s little sense in making that move right now.

So, who will be the Red Sox DH for 2024?

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There a few avenues the Sox can take. One option, is not having a DH. Boston can use it to keep certain bats in the lineup while also offering the player a bit of a rest day. Or, they could sign someone.

The obvious choice would be Justin Turner, who was the best part of 2023 Red Sox, and has expressed interest in a return. Whether or not he returns, is going to boil down to what the Red Sox are willing to spend on a player that will likely only be around for a year or two.


Can the Red Sox contend in 2024? Maybe. They’re in the unfortunate position of playing in one of the better divisions in baseball, but three Wild Card spots allow the possibility for them to sneak into the postseason.

However, with the lack of moves pertaining to starting pitching, the postseason doesn’t seem like a realistic goal for the Red Sox. They seem to be more focused on continuing to develop their young players and allowing the team to get a little bit better each year.

Without any major moves, it’s likely the Red Sox won’t be real contenders again for a few years. But, smaller goals, like finishing above .500 and getting out of last place, are certainly attainable for this team. And, honestly, would feel like a major improvement.