What happened: The Athletic's Chris Kirschner outlined a winter plan for New York that pairs a trade push for Cleveland Guardians outfielder Steven Kwan with a qualifying offer to retain reliever David Bednar. The offseason framework also calls for testing Luis Garcia Jr. across multiple infield positions and acquiring a right-handed-hitting catcher to balance the lineup. In the Arizona Fall League, 19-year-old Yankees middle infielder Dax Kilby went 7-for-18 in Week 3 with two doubles, a triple, a home run, and three stolen bases across four games.

Why it matters: Following consecutive early postseason exits in 2025 and 2026 after their 2024 Fall Classic loss, the Yankees are weighing winter trade upgrades to end a championship drought dating to 2009. With pitching coach Matt Blake signed to a three-year extension after guiding a staff that led MLB with a 3.23 ERA in 2026, the front office can focus its winter moves on contact hitting and infield versatility.

What to watch: New York approaches winter qualifying-offer deadlines as rival contenders, including the Chicago Cubs, also evaluate trade packages for Kwan.