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Which pitcher should the Yankees target? Ranking the available options

With Yoshinobu Yamamoto off the board, Brian Cashman has to look elsewhere for his rotation upgrade. But who should he make his new top priority?

Dylan Cease of the Chicago White Sox delivers a pitch against the Kansas City Royals during the first inning at Guaranteed Rate Field on September 12, 2023 in Chicago, Illinois. Photo by Michael Reaves/Getty Images

From the moment the blockbuster trade for Juan Soto became official, the New York Yankees have been focused on one thing: finding a way to upgrading their starting rotation behind Gerrit Cole. As if the sting of the franchise’s worst season in decades wasn’t enough, Soto’s looming free agency — not to mention two superstars who aren’t getting any younger in Cole and Aaron Judge — has put extra pressure on Brian Cashman and Co. to go all-in on contending in 2024. And it’s awfully hard to imagine them competing for anything without adding another arm or two, with Carlos Rodon and Nestor Cortes Jr. coming off two injury-plagued and ineffective seasons and Michael King now in San Diego.

It was hoped that said arm would be Yoshinobu Yamamoto. Alas, the $325 million man is now with the Dodgers — and the scramble for the best possible plan B is officially on. Over the last couple days, the Yankees have been linked to both Blake Snell and Dylan Cease, the top free agent and trade target available. Of course, Jordan Montgomery is also unsigned, as is Japanese star Shota Imanaga. Oh, and the Brewers might be dangling Corbin Burnes, while the Guardians look to be open to dealing Shane Bieber. There are a lot of potential directions Cashman can go, provided he acts with urgency.

But which direction would be best? That’s what we’re here to sort out. We’ve gone ahead and ranked all of the impact starters New York might feasibly add this winter — both free agents and pitchers widely assumed to be available via trade — in order of how well they fit the Yankees’ needs and resources. Note that this isn’t just a straight ranking of them as players; money and potential prospect cost obviously factor into the equation for Cashman, as they do here. Who tops the list? Let’s break it down.

Ranking potential Yankees pitching targets

1. Dylan Cease, Chicago White Sox

Yes, the righty is coming off a rocky 2023 season, in which his ERA ballooned to 4.58 and he allowed nearly a hit per inning. But his upside is undeniable: Few pitchers miss as many bats as Cease does (even in a down year, he ranked in the 84th percentile in whiff rate) or have better raw stuff, and he was the runner-up in Cy Young voting as recently as 2022.

And besides, this is as much about allocation of resources as it is about Cease’s ability. In a perfect world, the Yankees — who are, again, the New York freaking Yankees — wouldn’t be particularly concerned about money. Alas, we don’t live in that world; we live in Hal Steinbrenner’s world, and in Hal Steinbrenner’s world, New York is operating on a budget. Cease is under team control for two more years before hitting free agency. Signing Snell or Montgomery, on the other hand, will cost some $150-200 million — money that will directly impact the team’s ability to keep Soto around for the long haul.

So the choice is less “Snell or Cease” and more “Snell or Cease and the ability to match whatever other offers Soto gets”. Cease offers the upside of Snell with a reasonable floor at significantly reduced cost, and while the White Sox’ asking price in terms of prospects figures to be high, well, prospects exist to be traded. New York may not be able to win a bidding war with, say, the Orioles, especially after dealing much of their high-Minors depth in the Soto and Alex Verdugo deals, but if they can, it’s preferable to signing Snell or Montgomery to a contract you’ll likely regret down the line.

2. Jordan Montgomery, free agent

Let’s say the Yankees can’t in fact win that bidding war — the Orioles can simply offer more young talent if they choose to. Where should Cashman turn then? I think the answer has to be Montgomery. The lefty may not have Snell’s upside, but upside isn’t what this Yankees team needs — it needs reliability and, more specifically, it needs innings, and those are two things that Montgomery is nearly guaranteed to bring. Snell has cracked 130 innings just twice in his MLB career, and it’s not hard to imagine a scenario in which he, Rodon and Cortes all battle injuries and sink the Yankees’ chances before they even get off the ground. Montgomery will likely be had for (slightly) cheaper, and he’s likely to age better than a pitcher reliant on electric stuff to generate tons of swings and misses. Plus, pairing him with Cole means that two out of every five days you can feel good about your starter going deep into the game, giving your bullpen a bit of a break and giving your offense a chance to win. The lefty may not want anything to do with the team that dumped him at the 2022 trade deadline, but he insists there’s no bad blood, and Cashman better hope so.

3. Corbin Burnes, Milwaukee Brewers

Really, if you wanted to swap Burnes with Montgomery I wouldn’t blame you. He’ll be a free agent after 2024, but that’s a problem for next winter — again, the overwhelming priority is competing this season, while Soto is still under contract. Burnes dropped off his Cy Young pace last season, but he still posted a 3.39 ERA across 193.2 innings, and he’s been a consummate workhorse over the last few years for Milwaukee. Plus, that single year of team control is likely to drive his price down a bit. In terms of trade targets, I give the nod to Cease slightly due to his upside and extra year of control, but Burnes still ranks above most of the other options available: Acquiring the righty, getting a legit No. 2 for a year and then losing him to free agency while maintaining the flexibility to re-sign Soto is preferable to handing Snell the bag and hamstringing yourself moving forward.

4. Blake Snell, free agent

Honestly, we might be at the point where Snell has become underrated — yes, he has command issues, and yes, he’ll never be one to go too deep into games, and yes, there are durability concerns. But his ceiling is as high as anyone’s (see: those two Cy Young Awards) and his floor is higher than you think: In the four years between those Cy seasons, he pitched to a 3.85 ERA; at worst, you’re getting an above-average starter. Still, having said all that, I still feel like Snell should be something of a “break in case of emergency” option for New York.

To be clear, if it’s Snell or nothing, the choice should absolutely be Snell; New York cannot afford to be uncompetitive in 2024. But the lefty is unlikely to be a better investment than Montgomery if Cashman chooses the free-agent route, and the free-agent route itself carries a ton of risk. It’s one thing to compromise your ability to re-sign Soto by giving a long-term contract to a 25-year-old with the upside of Yamamoto; it’s another to do it with a 31-year-old who comes with his fair share of red flags.

5. Shane Bieber, Cleveland Guardians

Now we’re really into the “only if you absolutely have to” zone. That may be overly harsh to Bieber, who has two All-Star nods and a Cy Young Award under his belt. And the 28-year-old wasn’t bad last season — he still put up a 3.80 ERA (110 ERA+) over 128 innings. But everything about his profile appears to be trending in the wrong direction, from fastball velocity (down to the 13th percentile) to whiff rate to K rate to exit velocity. There’s a chance that he manages to piece together another above-average season through sheer guile and pitchability, and he’ll certainly come cheaper than Burnes or Cease. But can the Yankees really afford to take that risk in such an all-important season? If you could trust that Bieber would look anything like the pitcher he was from 2019-2022, you’d acquire him in a heartbeat, but his ceiling doesn’t seem worth his floor right now.

6. Shota Imanaga, free agent

Admittedly, there’s a chance that I’m proven very wrong here; several MLB teams seem to think so, given that the lefty is reportedly in line for a nine-figure pay day. But I remain very, very skeptical about Imanaga’s odds of sticking in a Major League rotation.

For starters, there are durability concerns. Imanaga is listed at 5’10, 176 pounds, and even those numbers might be doing him a favor. He’s never thrown more than 170 innings in a season, and he’s averaged about 155 frames over the last three years. The 31-year-old is also a big-time fly-ball pitcher, with only 35% of his batted balls earning a “ground ball” classification — something that would seem to spell danger with the short porch at Yankee Stadium. But the main reason for concern is his lack of a third pitch: Imanaga works almost exclusively off a rising low-90s fastball and a slider that earned a whiff rate north of 40% (an elite number) in NPB last season. That’s all well and good, but this may be an instance in which the step up in competition as he comes to the States may actually prove difficult — it’s simply harder to turn a big league lineup over multiple times when you’re not offering them multiple looks. Maybe Imanaga can pull a Carlos Rodon and make it work, although he doesn’t have nearly Rodon’s velocity. And, of course, Rodon’s struggles in 2023 are a perfect example of how thin the margin is for a pitcher with a limited arsenal. Again, if Imanaga is the only remaining option, you have to take the plunge. But I wouldn’t feel great about it given the Yankees’ needs and how crucial the 2024 season is.