The Philadelphia Phillies made the first big splash of the Winter Meetings on Tuesday, signing Kyle Schwarber to a five-year, $150 million deal. After finishing second in MVP voting in 2025, Schwarber cashed in on his last free-agent opportunity. The Phillies keep their designated hitter despite losing in the playoffs once again. How did both sides fare in the deal?
Schwarber had a lot of interest from teams across the league. His hometown team, the Cincinnati Reds, put together a public campaign for him to be the veteran presence in the clubhouse. The Baltimore Orioles matched Philadelphia's offer, while the Pittsburgh Pirates offered a four-year deal. But Schwarber will stick in Philadelphia with World Series aspirations.
Kyle Schwarber makes it rain in free agency
It is hard to have a better season leading into free agency than Schwarber had for the Phillies in 2025. He was the engine for their offense, bashing 56 homers and knocking in 132 runs. Both marks lead the National League, while 132 marked the most RBIs in the league. That paid off in spades, as he earned a monstrous contract in free agency.
After the 2025 season, Schwarber's career earnings are a shade under $100 million. His first deal with the Phillies was four years, $79 million, signed in the 2021 offseason. Defensive liabilities cost him in free agency the first time around, but he outperformed the deal dramatically. That earned him a significant raise this time around, sticking with the Phillies.
According to Ken Rosenthal, the Orioles offered Schwarber the same amount of money. The Phillies, however, offer a better chance to win the World Series in 2026. That bumps Schwarber's grade even more after a great deal. An A+ for Schwarber.
The Phillies enter an offseason of change

While the Phillies have been in the playoffs in each of the last four seasons, this was a disappointing campaign. They lost in the NLDS for the second consecutive season, losing both home games to the Los Angeles Dodgers. With Schwarber and catcher JT Realmuto hitting free agency, the path was laid for changes in South Philly.
The Phillies undoubtedly have more moves to come this offseason. They also have Ranger Suarez on the open market, who was one of their better pitchers last year. Alec Bohm trade rumors have been circulating this offseason as well, which could change things. Bryce Harper trade rumors have slowed down, thanks to Harper's own disgust with the conversation. Just because Schwarber is coming back does not mean that Philadelphia is running it back in 2026.
They did a great job bringing Schwarber back. Based on reports of his clubhouse leadership, he will be important to the new-look Phillies in 2026. There is a lot more time to go in the offseason, but the Phillies get an A on the Schwarber deal. It is expensive for a player in his age-33 season, but the designated hitter has earned it.
Final Kyle Schwarber thoughts
As the Winter Meetings wind down, Schwarber could open up the floodgates on the free-agency front. Edwin Diaz signed with the Los Angeles Dodgers minutes later, but the rest of Tuesday afternoon was quiet. The Phillies will be poking around some other players, as they have open spots in their rotation.
Schwarber would have been a great fit with any of the teams that offered him a deal. The New York Mets were also interested in Schwarber, but will likely turn to Pete Alonso now. Any of the teams that offered Schwarber an expensive contract could offer Alonso a similar one to fill a comparable hole.
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