The Baltimore Orioles made a splash at the 2025 Winter Meetings by agreeing to a five-year, $155 million deal with free-agent slugger Pete Alonso. This move, the biggest free-agent signing in franchise history by average annual value, bolsters their lineup amid an ultra-competitive AL East. The deal follows similar high-profile signings of Kyle Schwarber to the Phillies and Edwin Díaz to the Dodgers.
The 2025 MLB Winter Meetings in Orlando concluded with significant activity on the free-agent front, highlighted by three major deals that reshaped team rosters for the 2026 season. While the first day was quiet, the final two days brought notable signings, starting with Michael Soroka and Steven Matz on Monday. Late Tuesday, Kyle Schwarber agreed to return to the Philadelphia Phillies on a five-year, $150 million contract, prompting quick reactions from other teams.
Less than an hour later, Edwin Díaz inked a three-year, $69 million deal with the Los Angeles Dodgers, departing the New York Mets for the two-time defending World Series champions. The Orioles, who had been among Schwarber's suitors alongside the Red Sox, Mets, Reds, and Pirates, pivoted swiftly to sign Pete Alonso to a five-year, $155 million agreement. This marks the second-largest guaranteed free-agent contract in Orioles history, behind only Chris Davis' seven-year, $161 million deal from a decade ago.
Under executive Mike Elias, the Orioles had previously signed just one multi-year free agent, Tyler O'Neill to a three-year, $49.5 million pact last winter, followed by closer Ryan Helsley's two-year, $28 million deal earlier this offseason. Alonso's addition sets a new record for average annual value at first base and the highest in franchise history. He joins a promising young core including Gunnar Henderson, Adley Rutschman, Jackson Holliday, Colton Cowser, Samuel Basallo, and Jordan Westburg, plus recently acquired outfielder Taylor Ward.
Coming off a disappointing 75-win season, the Orioles aim to challenge the Blue Jays—who emerged as AL East frontrunners last year—the Yankees, Red Sox, and Rays. Baltimore continues seeking a frontline starter via free agency or trade. Meanwhile, the trade market simmers with names like MacKenzie Gore, Ketel Marte, and Tarik Skubal in discussions, though no blockbusters occurred during the meetings.
Earlier, Dylan Cease's seven-year, $210 million signing with the Blue Jays last month has cooled the starting pitcher market, per an NL executive: “Cease got more than most expected he would, so now every agent thinks their starting pitcher is going to get something similar or close to it.”
