New York Yankees Joel Sherman Yankees at crossroads with Jazz Chisholm, Anthony Volpe — starting with $23 million decision By Joel Sherman Published Oct. 14, 2026, 10:53 a.m. ET Yankees second baseman Jazz Chisholm Jr. reacts after striking out swinging to end the second inning during Game 2 of the ALDS against the Tampa Bay Rays at Tropicana Field, Monday, Oct. 5, 2026. Charles Wenzelberg for New York Post In Part 3 of our continuing series breaking down how the Yankees should navigate the offseason position by position, we stop at second base with two pertinent questions:
1. What did the Yankees learn from the Jazz Chisholm Jr. experience?
2. Will being a regular second baseman allow Anthony Volpe to flourish (here comes the key part) in New York?
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Chisholm’s two-and-a-half seasons as a Yankee felt akin to Stephon Marbury’s five seasons as a Knick – he was too talented not to fill up a boxscore and intersperse the spectacular. But it too often felt counter-productive to winning. It was showy, but not always sage. It reflected better on highlight reels than the scoreboard. If you looked at nothing but the numbers, you saw a better player than if you watched the games and saw him aimlessly wandering around with a defensive play in motion or getting picked off while fiddling with a sliding glove.
