If the Yankees want rotation upgrades, multiple moves are needed

Here I am again, bringing the irresistible Hot Stove Kool-Aid to my lips with the vim of a delusional sports talk radio caller.

I promised to retire as an Armchair GM, deeming it an exhausting waste of time, but as the offseason splutters to life, and the Yankees plot multiple paths to improvement, I have succumbed to conjecture once more. I’m keeping it light-hearted, though. Well, for now, at least. So far, I only have a few spreadsheets and a notebook filled with ideas. Bear with me on this.

Obviously, re-signing Juan Soto is the Yankees’ top priority, but there are several gaps on this flawed roster, as broached in my recent look at the complicated free agency of Gleyber Torres. Soto aside, the Yankees definitely need a first baseman, while solving the Rubik’s cube between second and third base is also an urgent need. Elsewhere, the bullpen requires surgery, and a replacement for Alex Verdugo in left field is also on the agenda.

If media reports are to be believed, however, the Yankees are also keen to upgrade their starting rotation, which surprises me given their current surplus in that department. MLB Trade Rumors has linked the Yankees to Jack Flaherty, Nathan Eovaldi and Max Scherzer; USA Today tabbed them as a suitor for Corbin Burnes; and seemingly every write-up on Rōki Sasaki – the latest Japanese uber phenom – mentions the Bronx as a possible landing spot. This week, Hal Steinbrenner himself even said his team will ‘take a deep dive into the starting rotation market,’ so the appetite for improvement seems genuine.

Nevertheless, I struggle to reconcile that desire with the facts. Namely, the Yankees already have six bonafide big league starters under contract for 2025 – Gerrit Cole, Carlos Rodón, Luis Gil, Nestor Cortés, Marcus Stroman and Clarke Schmidt. Throw in Will Warren, a highly-touted prospect who is 25 and ready for a prolonged big league look, and there are seven guys jostling for five spots as it currently stands. Therefore, if the Yankees do want to upgrade their rotation, multiple moves will be required, and at least one – if not two or three – mainstays will have to depart.

Yes, a team probably needs up to eight serviceable starters to get through a full regular season. And sure, the notion of ‘too much pitching’ is repeatedly quashed by unforeseen events. These ‘good problems’ tend to work themselves out, and at various times, every starter on the Yankees’ books has dealt with injuries, so hording depth is a wise idea. However, a team needs somewhere to stash its floating redundancy – in the bullpen or Triple-A, ideally – and those options do not smoothly apply to the Yankees’ cache. 

In theory, Stroman could be shunted to the bullpen, as he was down the stretch and through the playoffs this season – an indictment of previous front office strategies to be litigated another day. Meanwhile, Warren could start the season in Triple-A, and ride the Scranton-Bronx shuttle for another year, but at some point, he deserves more than a cup of coffee somewhere. Yet even those hypothetical moves leave a five-man rotation – Cole, Rodón, Gil, Cortés and Schmidt – that is broadly the same as 2024. 

That may not be a bad thing, necessarily. The Yankees’ starting corps was decent – if not spectacular – this year, ranking in the top-half of all MLB clubs in ERA, WHIP, WAR and strikeout percentage. Cole is an ace, Rodón has generally adjusted to New York, Gil just won Rookie of the Year honours, and Cortés and Schmidt are more than adequate back-end pieces. The Yankees could roll with that quintet and probably return to the playoffs in 2025 – offensive upgrades granted – but such stasis does nothing to improve their rotation. It does not allow them to upgrade, as suggested by several insiders and referenced by Steinbrenner. Hence my confusion.

In a vacuum, the Yankees should absolutely improve their starting rotation. Any team that just lost the World Series should leave no stone unturned while seeking marginal gains to get over the hump. That is especially true for the Yankees, whose current competitive window seems to be closing, thanks to the advancing age of Cole (34) and Aaron Judge (32). For context, though strong during the regular season, Rodón failed to last four innings in Game 2 of the Fall Classic, coughing up four earned runs on six hits. That is not good enough, ultimately. Reinforcements are needed to move the needle.

To do so – to supplement his rotation from the top down – Brian Cashman will first have to move a few incumbents. Cole, Rodón and Gil are probably ensconced, due to their contract situations and obvious upside, leaving Cortés, Stroman, Schmidt and Warren as trade bait.

Most likely, the Yankees will dump Stroman to create space. He was persona non grata in October, and an $18.5 million option for 2026 will vest if he pitches 140 innings next year. I generally like Stroman, who is a slightly above-average veteran with a splash of quality, but it is difficult to see him as anything other than a salary dump or throw-in at this stage. He is not a headline asset, and Cashman’s phone will not ring off the hook with suitors.

Warren, by contrast, does possess some value, and he has been coveted in trade talks for several years, including when the Yankees acquired Soto from San Diego last winter. I would not be shocked to see Warren packaged with a few other prospects to address the Yankees’ positional needs this winter. Indeed, such an outcome has felt inevitable for some time.                                                       

However, even if we assume Stroman is dumped and Warren starts the year in Scranton or on another big league club, that still leaves the Yankees with five starters for five slots. As such, to clear room for a rotation upgrade, Cashman would still need to move at least one of Schmidt or Cortés – the crux of this offseason dilemma.

Again, it is worth noting here that both Schmidt and Cortés have chequered injury histories. Cortés spent time on the injured list late in 2024, dealing with the kind of elbow flexor strain that often leads to more significant issues. Likewise, Schmidt was sidelined by a right lat strain for a good chunk of the season, before returning in September. Nevertheless, both are established big leaguers, and though each has spent time in the bullpen, they are unlikely to accept such a fate in 2025. Schmidt and Cortés are proven starters, and they would probably prefer to start anywhere else in the majors than languish in the Yankees ‘pen.

And so, to the hub of this particular ramble: realistically, to upgrade their starting rotation, the Yankees will have to move Cortés or Schmidt this winter. Such a move will likely net offensive help, with a free agent starter – Burnes, Fried, Snell, Buehler, Verlander, Scherzer, Bieber, Flaherty, et al – brought in. Alternatively, corresponding moves could yield an ace via trade – Sandy Alcántara, perhaps, or Luis Castillo. Other than that, I struggle to see this coming together.

Moreover, to reiterate, the mission here is to upgrade, not simply to add another arm. Logically, then, to improve the rotation, any starter who comes in must be better than Cortés, Schmidt, Stroman or Warren. To me, it makes little sense to add another starter in the same ‘good, not great’ category, ruling out potential targets like Eovaldi, Sean Manaea and Yusei Kikuchi. Ideally, you want somebody to replace Rodón as a Game 2 playoff starter, shifting everyone down a peg. Whether that is doable, in an offseason dominated by Soto, remains to be seen.

Still, it is fun to contemplate the first lever that must be pulled to open that avenue. What, in other words, could the Yankees actually get in return for Cortés or Schmidt? Well, the latter probably has more value due to his age (28), controlled status (three more seasons before free agency) and recent performance trends. Most teams would like to add a pitcher like Schmidt, and there are useful pieces available in trade that could help the Yankees in different scenarios.

One alignment that has repeatedly resurfaced in recent years is a hypothetical trade match with the Cubs. Chicago seeks young, cost-controlled starting pitching and perhaps a jolt to the top of its minor league pipeline, while the Yankees have theoretical interest – positionally and culturally – in Cody Bellinger, Nico Hoerner, Seiya Suzuki, Ian Happ and Isaac Paredes. I could certainly see a Cubs-Yankees blockbuster this offseason, reading between the lines. It makes too much sense not to be explored.

Meanwhile, further along I-55, the Cardinals also have a bunch of position players on the block, including Nolan Arenado, Brendan Donovan and maybe even Lars Nootbaar. All have previously been mentioned in pinstriped circles as potential targets, and each would make an intriguing addition to the Yankees.

Before we get too carried away, though, there is a wildcard looming over this entire debate: the aforementioned Sasaki, who will soon be posted by the Chiba Lotte Marines and journey to the US as an international amateur. Whichever team lands the 23-year-old prodigy – and they all have a theoretical chance, given the amenable nature of his restricted signing bonus – will almost certainly adopt a six-man rotation in 2025, similar to that favoured in Japan. Sasaki is such a young, precocious arm, no team will want to rush his development, providing another potential outlet for the Yankees – if they fight off the Dodgers and land the starlet.

Another similar wrinkle relates to Tomoyuki Sugano, the other lauded pitcher scheduled to swap Japan’s NPB for MLB. Make no mistake, the 35-year-old Sugano is of an altogether different ilk than Sasaki – a veteran, rather than a prospect – but he carries a compelling resumé, regardless. A two-time Sawamura Award winner, Sugano has dominated NPB for more than a decade while pitching to distinction for Team Japan. While more likely a rotation filler than a frontline difference-maker, Sugano has pitched in big games and carries stellar pedigree. Perhaps the Yankees court him as an under-the-radar X factor. 

Right now, of course, we do not know for sure whether Cashman will even attempt to improve his starting rotation at all. But if he does, two things are clear: space-clearing moves will be needed, and one of them will almost certainly involve Clarke Schmidt or Nestor Cortés.

My prediction? Bellinger and Hoerner for Schmidt, Stroman and a prospect – say, Everson Pereira.

I’ll hang up and listen.