The New York Yankees are focused on the postseason and are looking to end their World Series drought, which has lasted over 15 years. Nonetheless, there are takes and opinions to help the team improve this upcoming offseason.
It’s been a rollercoaster 2026 MLB season for Anthony Volpe, who was optioned to Triple-A in August and then recalled in September. Still, it might be in the 25-year-old’s best interest to get a fresh start elsewhere.
Christopher Kline of FanSided floated a trade idea that would send Volpe along with LHP Brent Headrick and LHP Kyle Carr to the St. Louis Cardinals for 24-year-old shortstop Masyn Winn.
“The Yankees’ lack of fundamental soundness on the defensive end has bitten them in the you-know-what all season, just like it did last year,” Kline wrote in a Sept. 16 article. “The hope was that top prospect George Lombard Jr. could steady the ship at shortstop, but he has stacked up errors left and right.
“It’s too early to write off the 21-year-old long term, but he could serve more comfortably at third or second — which is notable, since Jazz Chisholm Jr. is about to [be a free agent]. Winn immediately alleviates a ton of defensive issues for the Yankees, while his weaker bat would be well-protected in the American League’s most potent lineup.”
Yankees Have Assets to Trade for Cardinals’ Masyn Winn
Since being recalled on Sept. 9, Volpe has performed well. Entering Sept. 17, Volpe has been batting .348 with eight hits, a home run, seven RBIs, and three runs scored in seven games, per StatMuse. Meanwhile, Kline believes Volpe can benefit from a move, while the Yankees would upgrade their defense in the infield with Winn.
“New York has the resources to one day pay Winn his worth, too, although three additional years of club control means those conversations are in the distant future,” Kline added in his article. “This move allows St. Louis to bump Wetherholt to shortstop and plug in former top prospect Anthony Volpe at second base, where he has looked much more solid of late in New York.”
Anthony Volpe Would Benefit From a Move Out of New York
As for what Winn can bring to the plate, entering Sept. 17, he has a batting average of .237 with 107 hits, five homers, 54 RBIs, and 52 runs scored in 129 games this season, per StatMuse.
Moreover, Volpe would benefit from a move to the Cardinals, where Kline believes the team could move him to second base, where he might thrive. The two bullpen arms would bolster St. Louis’ bullpen and still have a handful of years under control to help in their rebuild.
“Volpe is a former Gold Glove shortstop whose defensive profile is very much salvageable, especially at a less demanding position,” Kline noted in his article. “He’s also a hitter with more upside right now, with the potential to add real pop to the back half of St. Louis’ lineup.
“The Cardinals also add high-leverage reliever Brent Headrick, with a 1.94 ERA and five years of club control, and 24-year-old southpaw Kyle Carr, a Triple-A arm who profiles as a potential back-end starter with plus command.”
Yankees, Cardinals Intriguing Trade Idea Involving Anthony Volpe