Pirates Offseason Plans Murky After Kyle Schwarber News

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The Pittsburgh Pirates are officially out of the race for Philadelphia Phillies free agent designated hitter Kyle Schwarber.
According to ESPN MLB insider Jeff Passan, the Phillies and Schwarber agreed to a 5-year, $150 million contract. At $30 million per year, the contract breaks a record for highest average annual value paid to a DH, per Passan. According to Pirates insider Alex Stumpf, sources told fellow MLB insider Mark Feinsand that the club offered Schwarber a similar deal, at four years for $120 million.
BREAKING: Slugger Kyle Schwarber and the Philadelphia Phillies are finalizing a five-year, $150 million contract, sources tell ESPN. The NL MVP runner-up, one of the best home run hitters and clubhouse leaders in baseball, is returning to Philadelphia.
— Jeff Passan (@JeffPassan) December 9, 2025
What Does Kyle Schwarber News Mean for Pirates?
Now that Schwarber has inked a new contract with his current team, the Pirates must pivot their offseason strategy. Pittsburgh is in desperate need of more offensive power, and could try to get some at the forthcoming Winter Meetings.
However, both fans and insiders are skeptical about the team's sincerity in pursuing a big-name free agent. The last time the Pirates signed a position player to a multi-year deal from free agency was a decade ago, and the team isn't exactly known for their big salary spend. Still, general manager Ben Cherington promised to spend more money on better players before Opening Day.
Another Big Swing?
Schwarber is not the only big hitting free agent the Pirates are interested in. They've been linked to Japanese superstar Munetaka Murakami, San Diego Padres first baseman Ryan O'Hearn and Seattle Mariners second baseman Jorge Polanco. Each man would be a huge addition to the Pirates lineup, but would also command an equally huge contract.
Without Schwarber on the table, Pittsburgh likely has the money to acquire a different free agent (including Diamondbacks' Ketel Marte). The biggest question becomes whether or not they are willing to extend that sort of contract, which would likely need to be overinflated.
Trade Market Heating Up
Then, there's the trade market. The Pirates are rich in pitchers that other teams could use, especially veteran starter Mitch Keller. Making a big trade for another powerful hitter could be worth it for a team with such impressive pitching depth, even if it means dealing Keller, which would also free up money for free agency additions.

The Pirates have been linked to several St. Louis Cardinals players including Brendan Donovan, Alec Burleson, Nolan Gorman and Lars Nootbaar. A deal between division rivals is always tricky to execute, but the Pirates could see serious benefit.
Regardless of the direction the Pirates go in, they'll need to make a big deal to convince fans that impressive baseball can return to Pittsburgh — and it won't be with Kyle Schwarber on board.

Delilah Bourque is a writer and copyeditor based out of Pittsburgh, PA. She received her Bachelor's degree from the University of Pittsburgh in 2021. After a few years in corporate marketing, she joined On SI as a full-time copyeditor and contributor to the New York Yankees On SI, as well as occasional contributions across the Pittsburgh Pirates and Pittsburgh Steelers on SI.