Just before the 2025 trade deadline came and went, the Yankees and Marlins were circling what could've been a blockbuster deal. Talks reportedly centered around a package that would have brought Sandy Alcantara and reliever Anthony Bender to the Bronx - a move that could’ve dramatically reshaped New York’s rotation. But in the end, the Yankees stepped back, opting to bet on internal development, particularly from right-hander Cam Schlittler, rather than parting with a top-tier prospect or young talent to get the deal done.
Fast forward to December, and that conversation may not be over.
According to former MLB general manager Jim Bowden, the Yankees and Marlins have already rekindled discussions involving Alcantara. Bowden went as far as to say that there's a "legitimate shot" the former Cy Young winner ends up in pinstripes - and that’s not just idle chatter. The Yankees have reportedly reached out to Miami again, and the idea of Alcantara in the Bronx is gaining traction.
Here’s where it gets interesting: Spencer Jones - the Yankees’ towering outfield prospect with middle-of-the-order upside - may once again be the sticking point. Jones was reportedly the name that put the brakes on a potential Alcantara/Bender deal back in July. Now, with the offseason in full swing, his name is back in the rumor mill.
Bowden even floated a bold scenario: trade Jones to Miami, then go out and sign Kyle Tucker to fill the outfield void. That’s a big swing, and while Tucker-to-the-Yankees feels more dream than reality at this stage, it’s worth noting that a group of 16 anonymous MLB executives recently pegged New York as a leading candidate to land the All-Star outfielder. Add in ESPN’s Jeff Passan hinting that a Yankees outfield shakeup is likely, and there’s clearly smoke here - even if the fire hasn’t quite caught yet.
If nothing else, it’s clear the Yankees are exploring multiple paths to upgrade their roster. While Japanese ace Tatsuya Imai remains the top pitching target, Alcantara represents a compelling fallback - albeit one with some question marks.
After missing the entire 2024 season recovering from Tommy John surgery, the 2022 NL Cy Young winner returned to the mound this year but struggled to regain his dominant form. He finished the season with a 5.36 ERA and 142 strikeouts over 174 2/3 innings - a far cry from his peak, but not uncommon for a pitcher in his first full season back from TJ.
Historically, it’s often the second year post-surgery when pitchers truly regain their edge.
Financially, Alcantara would carry an $11 million luxury tax hit in 2026, with a team option for 2027. That’s a manageable number, especially compared to what it might take to land or sign other frontline starters. And if he bounces back to anything close to his 2022 form, that deal could end up being a steal.
For the Yankees, the calculus is clear: do they believe Alcantara’s upside justifies parting with a top asset like Jones? And if they’re truly serious about making a run in 2026, can they afford not to make that kind of move?
It’s a familiar dance for GM Brian Cashman. Last winter, he talked up infielder Caleb Durbin as a potential key contributor - then flipped him days later for All-Star closer Devin Williams. So if Cashman starts singing Spencer Jones’ praises at next week’s Winter Meetings, don’t be surprised if that’s the prelude to a deal.
Whether or not Alcantara ends up in pinstripes, the Yankees’ offseason is shaping up to be anything but quiet. They’ve got the pieces, they’ve got the payroll flexibility, and they’ve got the motivation after another October that ended too soon. The only question now is: how bold are they willing to be?