Yankees have their pitching caught between a rock and a hard place

On Tuesday night, the news came out that Jordan Montgomery would be signing with the Arizona Diamondbacks, joining them on a surely-disappointing (for him) one-year, $25 million deal with a vesting option based on his number of 2023 starts. With that, this offseason’s solid and long drawn out pitching market closes, save for a few supplementary players still out there.

The Yankees, who will be without reigning American League Cy Young winner Gerrit Cole, were “in” on many of the biggest names, particularly at the end of the offseason, including Montgomery, Blake Snell, and Dylan Cease (via trade), but ultimately went without any of them. Although they have their reasons, which are considerable for the most part, their complacency even in the face of new-found holes in the roster points to something the Yankees have been dealing with for some time.

The Yankees should be a good team by most accounts; to wit, Baseball Prospectus and FanGraphs have them winning the AL East at 92 and 88 wins, respectively. Still, there were tactics that could’ve been pursued to better secure their outlook. Now, particularly with the expanded postseason, this half-going-for-it stance is more common, but in terms of being the best team you can reasonably be, there are obviously better alternatives.

Snell is a very good pitcher. He may not be the most aesthetically pleasing of the “good” pitchers, and as far as two-time Cy Young Award winners, he has a lot of variance, but he will help the Giants be a better team. Cease has similar pros and cons as Snell, but can be as dominant as anyone when things are clicking. Despite costing some prospect capital, he provides a major boost to the Padres rotation. Jordan Montgomery is coming off of the best season of his career, helping the Rangers win the World Series, and signed a very reasonable one-year deal as a 31-year old. Rockies aside, the NL West is a highly competitive division (like the AL East), and the Dodgers’ rivals had to make moves to try to compete with them — or at least bolster their Wild Card odds. The Yankees were capable of making any one of these moves. They didn’t.

Photo by New York Yankees/Getty Images

The Yankees are now confirmed to be without their foundational starter in Gerrit Cole for probably at least the first two months of the season, which was known before any three of these pitchers went to new ballclubs.

New York was not without its reasons. On the free agent side of things, there were some serious tax implications in play. In short, the Yankees would’ve had to pay a 110 percent penalty for any new 2024 commitments, and the way the market ended up for the two lefties, they would have a big bill to pay for just one or two years of either pitcher. If they ended up signing either, it would have been more in their interest to get a few more years. Which also begs the question, why not just do that?

Cease, as a trade candidate, would not have had the financial downsides as the free agent options, but he likely would have cost a top prospect, which the Yankees were unwilling to do. All of these are fair considerations, in all reality, but that doesn’t change the fact that the Bombers ultimately didn’t see any of these options through, and they may find themselves stuck in the middle again.

This is an issue going back to last year’s Trade Deadline, where they didn’t buy, and they didn’t try a minor re-tool. They were complacent and caught betwixt and between. This isn’t to say this will be a bad team in 2024—I don’t think that’s the case—but their direction of late can come across quite unclear.

The Yankees gave up quite a bit to bring in Juan Soto, which is never a bad move, but he’s only guaranteed to be in pinstripes for one season as things stand. And it’s worth considering that they traded away pitching depth to make the deal happen. Either way, the present moment seems like an opportune time for this team to do everything it can to take advantage of having his generational talent in the fold.

Now, the Yankees are headed for Opening Day without Cole, and without any other top level starter that was available to them. None of these respective deals may have been slam dunks, but in a league where FanGraphs projects 15 teams to finish between 80 and 85 wins, every marginal step forward matters. It’s fair to hope that Carlos Rodón turns things around, and that Nestor Cortes and Marcus Stroman can help carry the load, but another trustworthy arm could have added a lot at the moment. There are worse things, but getting stuck in the middle can be as frustrating as anything.