The Philadelphia Phillies could find themselves at the center of a major offseason discussion as the New York Yankees navigate a tricky 2026 winter. With Jazz Chisholm Jr. generating trade interest across the league, attention is turning to which club is best positioned to make a serious push. The Phillies, consistent contenders in the National League East, stand out thanks to their prospect depth and roster flexibility, giving them the ability to put together an offer that aligns with both the Yankees’ short-term needs and their longer-term plans.
Chisholm is coming off a standout 2025 campaign that marked the most productive season of his career. The 27-year-old hit .242/.332/.481 while setting personal bests with 31 home runs, 75 runs scored, and 80 RBIs. He also swiped 31 bases, tying for sixth in the American League. That blend of power, speed, and solid defense makes him an attractive target for teams looking to upgrade the middle of the field. With only one year left before free agency and an arbitration salary projected at $11.7 million, the Yankees are reportedly open to discussions as they retool their roster.
Philadelphia appears to be a natural fit. The Phillies have already invested heavily in their lineup, but any change among their veteran infielders could create an opening to strengthen depth without compromising their title aspirations. Chisholm’s versatility, athleticism, and All-Star résumé would give manager Rob Thomson more flexibility while adding another dynamic element to an offense designed to contend every season.
Proposed trade framework for Jazz Chisholm Jr.
Phillies receive
2B/OF Jazz Chisholm Jr.
Yankees receive
2B Bryson Stott
OF Justin Crawford
Why the deal works
Stott would give New York an immediate solution at second base, helping to address an offensive gap in the infield. Although his production dipped in 2024, when he posted a .671 OPS, he remains a reliable defender and a steady contributor with speed, averaging more than 32 stolen bases per season. At 27 and under team control for several more years, Stott offers value and cost certainty.
Crawford adds significant upside to the Yankees’ farm system. The Phillies’ third-ranked prospect, the 21-year-old hit .325/.390/.421 at Triple-A Lehigh Valley in 2025. Drafted 17th overall in 2022, Crawford has impressed with his bat-to-ball skills, plate discipline, and elite speed, traits that fit well with modern roster-building philosophies.
For the Phillies, the move would address infield depth with a proven All-Star who can contribute immediately. Parting with Crawford would be the biggest sacrifice, but acquiring a player of Chisholm’s caliber typically requires a premium prospect.
In the end, this framework benefits both sides. The Yankees gain a high-upside prospect and a ready-made infielder, while the Phillies add an impact talent capable of helping them chase another championship. As rivals look to reshape their rosters, this type of deal illustrates how meaningful offseason trades can come together.