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Veteran DH Hits Free Agency for Second Time

November 5, 2025 by Last Word On Baseball

Veteran designated hitter Kyle Schwarber is set to become a free agent for the second time in his career, positioning himself as one of the most impactful left-handed power bats on the market. Known for his elite home run ability, high walk rate, and clutch postseason track record, Schwarber enters this free-agency cycle with a resumé that blends historical significance, modern slugging production, and leadership qualities coveted across MLB.

Oct 9, 2025; Los Angeles, California, USA; Philadelphia Phillies left fielder Kyle Schwarber (12) doubles in the first inning against the Los Angeles Dodgers during game four of the NLDS round for the 2025 MLB playoffs at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-Imagn Images

Kyle Schwarber: 2025 MLB Free Agent Profile

Early Career

Schwarber debuted with the Chicago Cubs in 2015. Despite missing nearly the entire 2016 regular season due to a torn ACL and LCL, Schwarber returned in dramatic fashion for the World Series and delivered critical at-bats that cemented his legacy in Chicago, quickly becoming a postseason hero, helping the franchise capture its first World Series title in 108 years in 2016. His October legend status propelled him into mainstream recognition and highlighted his elite competitive makeup.

Following that iconic championship run, Schwarber’s next four seasons in Chicago were uneven, marked by streaky power production, mechanical adjustments, and defensive limitations. While Schwarber consistently provided home run value, the combination of fluctuating batting averages, strikeout rates, and defensive metrics ultimately led the Cubs to non-tender him following the pandemic-shortened 2020 season. It was a surprising move given his postseason pedigree and clubhouse presence, but it opened a new chapter.

Schwarber signed a one-year “prove-it” deal with the Washington Nationals ahead of the 2021 season and delivered a strong first half, reigniting his value and showcasing his improved plate discipline and power stroke. Washington capitalized at the trade deadline, dealing him to the Boston Red Sox. Schwarber immediately made an impact in Boston, posting a .292 average with seven home runs across 41 games and helping the Red Sox reach the ALCS before falling to the Houston Astros. His short tenure in Boston reaffirmed his identity as a premier power bat capable of changing a lineup’s dynamic instantly.

Phillies Tenure

Ahead of the 2022 season, Schwarber inked a four-year, $79 million contract with the Philadelphia Phillies. He has since become a cornerstone of their offense, leading with elite power, exceptional on-base ability, and veteran experience. Schwarber has consistently ranked among MLB leaders in home runs and walks, emerging as one of the most feared designated hitters in the game. 

Additionally, his postseason leadership and presence in a high-octane Phillies clubhouse have reinforced his reputation as a culture driver and tone-setter in competitive environments, which helped lead the Phillies to an NL Pennant in 2022.

“I’m just happy I’m player No. 12.”

Kyle Schwarber joins the show to talk about his outstanding season in Philadelphia and being an NL MVP Award finalist. https://t.co/pSHFkQw4dk pic.twitter.com/eWn5ofCBYn

— MLB Network (@MLBNetwork) November 4, 2025

Contract Outlook

As Schwarber approaches free agency once again, he is expected to command a lucrative long-term deal. Current projections place him in the four-to-five-year range with a total value of $120–$150 million, reflecting his elite offensive production, durable power profile, and ability to thrive under postseason pressure. 

Schwarber will draw significant interest from teams seeking a middle-of-the-order DH, including potential reunions with the Phillies, Cubs, and Red Sox. Additionally, other clubs, such as the New York Mets, are likely to value his left-handed power, well-documented postseason success, and strong clubhouse impact. In a league where elite slugging and playoff pedigree carry premium value, Schwarber stands positioned to secure another major contract and continue his role as one of MLB’s elite designated hitters.

 

Main Photo Credit: Jayne Kamin-Oncea-USA TODAY Sports

The post Veteran DH Hits Free Agency for Second Time appeared first on Last Word On Baseball.

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