All indications are the New York Yankees will make a significant addition to their rotation before spring training, blessedly bumping promising arms Will Warren and Clayton Beeter back to "sixth/seventh starter" status (their time will still come).
Only problem? As the Yankees' fortitude increases in the search, the market dwindles. Jordan Montgomery seems to prefer Texas, if all things are equal, and the Rangers are working on securing the money via a new TV deal (side note: the World Series champions should never, ever have to scrap this hard to be televised, what are we doing?). Blake Snell's "private interest" in the Yankees has been mentioned in recent days, but unless he's willing to take a high-AAV, short-term deal, this just feels like Scott Boras' manipulative handiwork. Shōta Imanaga, for all intents and purposes, doesn't interest the Yankees at all.
So, if not the Big Three in free agency, where will the Yankees turn? Dylan Cease is prohibitively expensive and posted a mid-4.00s ERA last year. Unless the Yankees can get the Juan Soto trade package refunded, they probably can't (or won't) compete there. Corbin Burnes is more likely to go at the deadline; the Brewers intend to compete. Shane Bieber's elbow may or may not be a bed of shredded lettuce; either way, the Yankees don't seem inclined to find out, swinging a Cody Morris trade before letting the Guardians head out elsewhere.
That leaves the Marlins (Edward Cabrera, Jesus Luzardo, Braxton Garrett), as well as several names MLB insider Joel Sherman floated in a Thursday column. According to Sherman, the Yankees might circle back to Cleveland and entertain an expensive trade for childhood Yankee fan Triston McKenzie. They could also dive deeper into several pitchers whose current teams are embracing "listening mode": Tarik Skubal of the Tigers, Bryce Miller of the Mariners and Mitch Keller of the Pirates.
Could the New York Yankees trade for Tarik Skubal (Tigers), Mitch Keller (Pirates)?
The Yanks have certainly gone to the Pirates' well before; Gerrit Cole began his career there, and was nearly dealt to New York before Pittsburgh's front office chose Houston's inferior offer. Perhaps they learned their lesson in 2021 when they agreed to swap Jameson Taillon to New York, or later in the summer, when they facilitated Clay Holmes' move. There's a reason why the Yankees were considered a Bryan Reynolds favorite last winter when he was briefly on the trade market, and it wasn't just because he's a lefty outfielder (Ok, maybe it was, actually).
The idea of having a three-lefty rotation is more appealing with a truly high-ceiling option like Skubal (2.80 ERA, 2.0 bWAR in 15 starts/80.1 innings last season with the Tigers) than with an innings-eater like Montgomery whose stuff profiles similarly to Nestor Cortes Jr.'s arsenal. Running out a trio of left-handers in the stadium could trick opponents into ignoring the short porch with a righty-heavy lineup, but if the velocity stays in the low-90s, a bad day could leave them gasping for air against any lineup.
In all, this list is packed with projectable arms who wouldn't provide as much stability as Montgomery and would also cost an arm (left or right) and a leg to acquire. The bottom line? You could add as many names as you want to the Yankees' pool. They're not going to get what they believed they needed: Yoshinobu Yamamoto.