Everything is happening super quickly for the Boston Red Sox this offseason. Sure, it has pressure, but it brings promise too. And after a rollercoaster year that showed their brilliance and shortcomings, the team now stands at a crossroads. Their young core has shown resilience, but there are weaknesses across the board, which are keeping Boston from making a deep postseason push.

As chief baseball officer Craig Breslow, SEO Sam Kennedy, and manager Alex Cora prep to face the media and dissect the season, the priorities are clear. To get back into serious contention, they need to address three major problems. And the uncertainty around Bregman’s future only makes the task more complicated.

So, let’s break down where Boston needs to pay attention this winter.

Adding a big bat is prerogative for the Boston Red Sox!

The Boston Red Sox’s offense was a big question mark this year. Despite some breakout moments, they were hugely inconsistent. On paper, though, the numbers look pretty—a .254 team average (fourth in MLB), a .745 OPS (ninth), and a league-leading 324 doubles. People say numbers don’t lie, but they sometimes do. Too often, Boston fell flat in the key moments, especially with runners in scoring positions.

Plus, trading Rafael Devers left a massive gap in the lineup. Roman Anthony did his best to fill in, but the oblique injury wrecked him. Bregman also provided a spark early, hitting .938 OPS through 52 games, but then a quad injury cost him seven weeks. So those absences left a gap in the lineup. Now with Bregman entering free agency and Trevor Story opting into his contract, Boston faces a crucial question: who will be their offensive anchor next season?

Triston Casas is expected to be ready for the opening day after his knee tendon injury. But returning from that setback is no small thing. If Bregman leaves, then Boston can’t go into 2026 without a power threat right in the middle of the order. Pete Alonso would be a dream addition, and he is expected to opt out of his final year with the Mets.

Given he hit 41 doubles, 38 homers, and is a presence like no other, the Red Sox could really get the help they need from him. There is also Kyle Schwarber, a name that Boston fans are familiar with. He had a short stint with Boston back in 2021, and now, after his 56-homer season, reuniting with him could transform the Red Sox’s lineup.

The bottom line is that Boston needs a big bat who can stay on the field and take off the pressure from the young hitters.

Strengthening the Defense

Now, no matter what big bats Boston gets or how great their offense is, the defense can make or break a season, and this has been an Achilles heel for them for years. Despite the presence of Gold Glove Alex Bregman and a healthy Trevor Story, the Boston Red Sox led all of baseball in errors this season, standing at 116.

That’s concerning, given this is their three straight year with over 200 errors. Not ideal when you want to go deep into October. And Story did stabilize the dense, but the fatigue caught up to him, and in September, he committed to throwing errors in a single week.

By the season’s end, he finished with a -9 Outs Above Average (OAA)–the worst of his career. Bregman, on the other hand, felt steady with a +3 OAA, but given that he has opted out, his future in Boston seems on shaky ground.

Now there is growing speculation about shifting Trevor Story to second base. It is where he has played well before. When he signed with Boston in 2022, he was at second along with Xander Bogaerts, and he thrived there. Now, with Marcelo Mayer still recovering from wrist surgery, there is a real path where Mayer slides into shortstop and then Story shifts back to second. So a Mayer-Story combo in the middle, plus maybe Bregman if they can get him back at third, can help solidify Boston’s defence.

Adding a True No. 2 Starter Behind Garrett Crochet

The Boston Red Sox found the ace they have been in the hunt for in Garrett Crochet. But one ace is not enough for today’s baseball. Injuries and inconsistencies plague teams all season, and that highlights a lack of a dependable No. 2 starter.

Lucas Giolito and Brayan Bello filled in the No. 2 and No. 3 roles this season, but ideally they should be the team’s middle-of-rotation anchors. Plus, injuries to Kutter Crawford, Tanner Houck, and others forced them to rely on rookies like Payton Tolle and Connelly early. For now, adding another proven front-line starter has to be at the top of the list.

There are many arms expected to hit the market, like Dylan Cease, Merrill Kelly, and Framber Valdez. While none of them come cheap, they can all give the stability to the Red Sox, and it’s what they need. Jack Flaherty could be another fallback option, but Boston might have eyes on the price this time–Paul Skenes.

Skenes is the creme de la creme of aces this time. Bleacher Report’s Zachary D. Rymer, in fact, lists Boston as a trade fit for Skenes—one of the best pitchers in baseball. He has a 1.96 ERA in 55 starts, and that could form one of the deadliest duos along with Crochet. Skenes is under team control through 2029. But ESPN’s Jeff Passan has suggested that the Pirates might consider sending him off in case they can’t sign him long-term. This off-season will be pivotal for Boston. There is also Tarik Skubal, whom Boston can look into.