Kyle Schwarber: Pirates' Bold Pursuit vs. Phillies' Free Agency Dance

The Kyle Schwarber Sweepstakes: Pirates Make Shocking Play as Phillies Fight to Keep Star

The MLB offseason is heating up with one of the most compelling storylines: the pursuit of power-hitting Kyle Schwarber. While the Philadelphia Phillies prioritize re-signing their MVP runner-up, a surprising contender has entered the fray. The Pittsburgh Pirates, a franchise historically known for fiscal restraint, have emerged as aggressive suitors for Schwarber, signaling a potential seismic shift in their roster-building philosophy. This high-stakes free agency saga could reshape both franchises' futures.

Pirates Unprecedented Aggression: A New Era in Pittsburgh?

Under GM Ben Cherington, the Pirates are showing financial flexibility unseen in years. With ownership potentially approaching a $40 million spending limit, Pittsburgh made headlines by pursuing both Schwarber and Josh Naylor. While Naylor ultimately re-signed with the Mariners for a five-year, $92.5 million deal, the Pirates reportedly offered over $78 million—nearly double their previous free-agent record set by Francisco Liriano's $39 million contract in 2014.

This willingness to spend stems from urgent needs. After seven consecutive losing seasons and a 2025 campaign where pitching phenom Paul Skenes was let down by a woeful offense, Pittsburgh is desperate for impact bats. Schwarber's 34 home runs, 104 RBIs, and .882 OPS make him an ideal target, though his age-33 season and DH-only status present challenges. The Pirates' interest suggests they might finally abandon their "spread-the-money" approach in favor of a marquee acquisition.

Kyle Schwarber connects for a home run during the 2025 season, showcasing the power that has made him a hot commodity.

Phillies' Priority: Keeping the Heart of the Order

Across the league, the Phillies remain Schwarber's most motivated suitor. President of baseball operations Dave Dombrowski has made it clear re-signing the slugger is essential, calling him "integral to the entire operation." However, Schwarber's camp—led by Excel Sports Management—plays a patient game, exploring all options in a weak outfield market.

The Phillies face competition from unexpected places. The Boston Red Sox, with manager Alex Cora's strong bond to Schwarber, could pivot to him if they avoid adding another lefty DH. The New York Mets might pursue him if they move on from Pete Alonso, while the Toronto Blue Jays could enter if Bo Bichette departs. Yet Philadelphia remains the favorite, projecting to offer a five-year, $135 million contract per MLB Trade Rumors—despite Schwarber's defensive limitations and age concerns.

Phillies fans celebrate during a 2025 game, highlighting the team's desire to retain Schwarber and contend.

The Market Dynamics: Age, Role, and Contingency Plans

Schwarber's free agency presents a fascinating case study. His age-33 season and transition to full-time DH raise questions, but his elite power (.212 ISO in 2025), consistent production, and clubhouse leadership mitigate concerns. Teams like the Pirates and Phillies believe his bat outweighs his defensive liabilities, especially with designated hitter positions now prevalent across MLB.

For Pittsburgh, pursuing Schwarber doesn't necessarily mean incumbent first baseman Spencer Horwitz is expendable—Horwitz could slide to DH if Schwarber arrives. Meanwhile, the Phillies are preparing contingency plans. They've explored trade targets like Arizona's Ketel Marte and Minnesota's Byron Buxton but are hesitant to part with top prospect Andrew Painter. Their bullpen shuffle—fielding offers for lefties Matt Strahm and José Alvarado—could fund additional moves if Schwarber signs elsewhere.

What's Next? A Winter of Decision

As the offseason unfolds, Schwarber's destination will hinge on balancing his desire for a multi-year deal with contenders' budgets. The Pirates' aggressive pursuit could force a bidding war they may ultimately lose to bigger markets, but their involvement alone marks a significant moment for a franchise long mired in frugality. For the Phillies, retaining Schwarber is the priority, but Dombrowski acknowledges they must be ready to pivot if negotiations stall.

One certainty: wherever Schwarber lands in 2026, he'll bring a powerful middle-of-the-order presence. The question is whether it'll be with a surprising new team in Pittsburgh or with the Phillies organization he helped elevate to baseball's elite.