The Boston Red Sox can look back on the 2025 season with a sense of progress, but also with the realization that there’s still plenty of work to be done. After missing the playoffs for three straight years, the Red Sox finally returned to the postseason, reigniting hope among their loyal fan base. Their mix of young talent and veteran leadership showed flashes of what could be a promising future.
One of the brightest developments was the rise of rookie Roman Anthony, whose smooth swing and advanced approach at the plate had many envisioning him as the franchise’s next cornerstone player. Unfortunately, his breakout campaign was cut short in early September by an oblique injury that sidelined him for the remainder of the regular season and kept him out of the Wild Card series against the New York Yankees.
Without Anthony’s bat and several other key contributors down the stretch, the Red Sox couldn’t muster enough offensive firepower to advance. Their lack of consistent power and run production ultimately proved costly against a deeper, more experienced Yankees squad.
Now, the organization heads into what promises to be a pivotal offseason. Chief Baseball Officer Craig Breslow and manager Alex Cora know that if Boston wants to sustain its playoff return — and push further — the team must add impact talent.
The loss of Alex Bregman, who opted out of his three-year, $120 million deal, leaves a glaring hole in the lineup. The front office will likely make a strong effort to re-sign him, as his leadership and clutch bat were invaluable. However, even if Bregman returns, the Red Sox will still need another major offensive weapon to truly compete with the American League’s elite.
That’s where Kyle Schwarber could come in. The Philadelphia Phillies slugger, who’s set to hit free agency after the World Series, would be a dream addition for Boston. Schwarber’s familiarity with Fenway Park and his history of postseason success make him an ideal fit as a designated hitter in Cora’s lineup.
Coming off a massive season in which he played all 162 games, hitting 56 home runs, driving in 132 runs, and posting a .240/.365/.563 slash line, Schwarber remains one of the most feared power hitters in baseball. Yes, he strikes out often — 197 times, to be exact — but his elite on-base skills and game-changing power would give Boston the middle-of-the-order presence they’ve been missing since the days of J.D. Martinez.
It won’t be easy, as Schwarber will draw significant interest from multiple teams and the Phillies are expected to make a strong push to keep him. But if the Red Sox want to take the next step from playoff hopefuls to legitimate contenders, reuniting with a proven slugger like Schwarber could be exactly the move that puts them over the top.
Schwarber has proven himself time after time
There’s no denying that Kyle Schwarber is far more than just a one-year wonder — he’s been one of baseball’s most consistent and feared power hitters for nearly half a decade. The 32-year-old slugger has built an impressive résumé during his time with the Philadelphia Phillies, becoming a cornerstone of their offensive success and a symbol of durability and leadership.
Since joining the Phillies in 2022, Schwarber has been on an extraordinary tear. He launched 46 home runs in his debut season, followed by 47 homers in 2023, and 38 long balls in 2024 — before exploding for 56 in 2025. Over that span, he has driven in more than 100 runs in each of the past four seasons, proving that his power and production are anything but a fluke. Few players in the modern game have matched his combination of raw strength, discipline, and clutch performance.
Before his Philadelphia stint, Schwarber made his mark with the Chicago Cubs, where he spent the first six seasons of his career. His legacy in Chicago is forever tied to the Cubs’ historic 2016 World Series championship, when he returned from a devastating knee injury to deliver key hits and help end the franchise’s 108-year title drought.
Following his Cubs tenure, Schwarber split the 2021 season between the Washington Nationals and the Boston Red Sox, and his brief time in Boston left a lasting impression. In just 41 games with the Red Sox, he quickly became a fan favorite, slashing .291/.435/.522 with 7 home runs and 18 RBIs. His infectious energy, leadership in the clubhouse, and ability to thrive under pressure made him an instant hit with both teammates and fans.
At 5-foot-11 and 230 pounds, Schwarber brings more than just power — he brings presence. He’s a player who thrives on big moments, and he’s proven that repeatedly in both the regular season and postseason. His combination of patience at the plate, power to all fields, and competitive spirit makes him one of the premier sluggers of his generation, right alongside Shohei Ohtani, Aaron Judge, and Cal Raleigh.
Now entering free agency, Schwarber is poised to command one of the richest contracts ever awarded to a designated hitter — and rightfully so. For the Red Sox, the chance to bring him back to Fenway Park should be a top priority. His left-handed power is tailor-made for the Green Monster, and his veteran leadership could fill the void left by Alex Bregman’s opt-out.
In many ways, Schwarber could play the same transformative role that J.D. Martinez did during Boston’s 2018 World Series run — a steady, game-changing presence in the heart of the lineup who can turn any at-bat into a highlight. If the Red Sox are serious about returning to championship contention, signing Schwarber wouldn’t just be a smart move — it would be a statement that Boston is ready to win again.
Multiple teams are likely to pursue Schwarber
At the top of the list of potential suitors for Kyle Schwarber, the Philadelphia Phillies remain the clear favorites. After all, Schwarber has become a beloved figure in Philadelphia, and his monstrous left-handed power fits perfectly in the hitter-friendly confines of Citizens Bank Park. He’s also been a leader in the clubhouse, setting the tone for a team that has consistently contended for the postseason during his tenure. There’s no question that the Phillies want him back — and Schwarber himself has made it clear that he enjoys playing there. That combination will make it extremely difficult for any team, including the Boston Red Sox, to lure him away.
Still, the Chicago Cubs could very well enter the conversation. Bringing Schwarber back to Wrigley Field would make for a storybook reunion. The Cubs had a strong 2025 campaign, returning to the playoffs and even taking down the San Diego Padres in the Wild Card round. However, their lack of consistent power was glaring in the NLDS loss to the Milwaukee Brewers, a series that ended in five games. Adding Schwarber’s left-handed bat back into the middle of their lineup could help elevate them from postseason participants to legitimate World Series contenders.
As for the Brewers, their situation is different. Despite a dominant regular season, Milwaukee’s offense has sputtered in the postseason, and they now find themselves on the brink of elimination in the NLCS against the Dodgers. Schwarber would certainly give their lineup the power punch it lacks, but the franchise’s long-standing financial caution makes it highly unlikely that they’d be willing to offer him the kind of deal he’ll command on the open market.
And that market will be competitive. Schwarber’s asking price is expected to hover around $120 million over four years, a figure that reflects his elite production and star power. The Phillies are more than capable of meeting that number — and likely will. But for the Red Sox to have a real chance, they’ll need to go beyond it. That means owner John Henry and the Boston front office may have to dig deep and offer something closer to four years and $130 million to make a convincing pitch.
Henry has historically been reluctant to hand out massive long-term contracts, especially to players in their 30s, but if he’s serious about bringing another championship back to Boston, this is the kind of investment it may take. Schwarber’s proven track record, leadership, and familiarity with Fenway Park make him more than worth the price tag — he could be the missing piece that turns the Red Sox from a playoff hopeful into a true World Series threat once again.
Steve Silverman has been covering the NFL for more than 35 years, with his work appearing in ESPN Magazine, Bleacher Report, CBS Sports, Pro Football Weekly, and Forbes.com. He is also the author of 10 books, including “Who’s Better, Who’s Best in the NFL.”
