Should the Yankees pursue a late reunion with free agent starter?

MLB: World Series-Texas Rangers at Arizona Diamondbacks

Nov 1, 2023; Phoenix, AZ, USA; Texas Rangers starting pitcher Jordan Montgomery (52) celebrates defeating the Arizona Diamondbacks to win the World Series in game five of the 2023 World Series at Chase Field. Mandatory Credit: Matt Kartozian-USA TODAY Sports

Jordan Montgomery and the New York Yankees are a natural fit; the left-hander is coming off his best season and desperately needs to find a home while the rotation in the Bronx is in flux. The two are extremely familiar with each other, as it was the Yankees who spent a fourth-round pick on Montgomery in the 2014 MLB Draft out of The University of South Carolina. He had some strong seasons in the Bronx before being traded to the St. Louis Cardinals and seeing his career take off, eventually heading to Texas and winning a World Series as their ace.

Right now, the Yankees are without Gerrit Cole, who they hope to get back some time in late May or June and slot at the top of their rotation. Jordan Montgomery could provide a solution to some of those questions in the rotation, but given how heavily they would be taxed on their payroll, should they still sign him?

Jordan Montgomery Makes Too Much Sense For the Yankees

The Yankees are projected to get a 12.5 fWAR from their rotation, which would be the 14th-best mark in the league, and while that’s not awful, it’s also not great. There’s certainly room for improvement, and Jordan Montgomery would provide that impact in a hurry. Prospects like Will Warren and Luis Gil have made names for themselves in Spring Training, but it’s important to note that they are just prospects; you can’t reasonably expect much more than solid production from either of them as starters. I have high hopes for both Warren and Gil, with Warren being someone I’ve advocated heavily for in recent weeks to win the final spot in the rotation.

Without sounding like a Scott Boras mouthpiece, Montgomery would provide the Yankees with a frontline starter who can help anchor their rotation, and while his 2023 season seems a bit flukey, he made some tangible changes to improve his arsenal. After being traded to the Rangers, he would cut his sinker usage down by about 7%, relying more on his four-seamers and curveballs, specifically against right-handed batters. His groundball rate took a hit, but his whiff rates increased and we also saw his contact management improve as well.

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Improving your pitch selection is an important part of having success at the Major League level, and it seems that Montgomery has found a pairing with his fastballs and curveballs. His curveball has the movement profile of what some within the pitching world call a ‘deathball’ and since he releases it from the same slot as his fastball, they’re very effective at throwing opposing hitters off when they’re sequenced together.

“When it comes out of his hand, it looks like a fastball, that makes it a little more difficult. The way he releases the ball, the angle he releases it, makes it a little bit more difficult to pick it up and makes it look like a fastball.”

– Yordan Alvarez

Jeff Passan of ESPN covered the pitch and how it helped Jordan Montgomery dominate hitters in the ALCS against the Houston Astros, and perhaps that combination could flourish in the Bronx as well. We all know that the durability and consistency that he brings on a game-to-game basis can be highly valuable to this rotation, especially after losing their workhorse in Gerrit Cole. Sure, Montgomery isn’t going to rack up strikeouts the same way Gerrit Cole does, but if he’s preventing runs reliably, does it truly matter?

There is no replacement for Gerrit Cole, and even if there was, they’re not going anywhere at this point of the offseason, and that was true even when Blake Snell was a free agent. The Yankees are in a win-now window, and if winning a World Series means running the highest payroll in MLB history, then so be it.

Credit: Kim Klement-USA TODAY Sports

It’s hard to argue that Hal Steinbrenner hasn’t made the financial commitment necessary for the 2024 Yankees to win the World Series, but they could and should go the extra mile for Jordan Montgomery. This isn’t just a move for April either, this one can pay huge dividends when we get to the postseason. Having Gerrit Cole and Jordan Montgomery anchoring a rotation that could get a bounceback season from Carlos Rodon or Nestor Cortes while having the steady presence of Marcus Stroman is certainly an enticing idea. Add on any potential deadline moves, and you have a terrifying rotation that becomes a strength for the team instead of a weakness.

We’ve seen how bad things can get at a position when depth isn’t properly addressed following an injury, as the Yankees are scrambling for a utility infielder that can help them at third base. Relying on the oft-injured DJ LeMahieu and the unproven Oswald Peraza could lead to disaster at the hot corner, and hoping that your rotation sticks together after losing your projected innings eater might lead to even more uncertainty when other guys inevitably get hurt. It’s not that injuries are predictable, but they are unavoidable, and the Yankees got a cold reminder of that last season.

Jordan Montgomery isn’t a Cy Young winner, but if the Yankees can land him at a somewhat reasonable price with opt-outs, he could give the team the right kind of boost they need. He doesn’t come with any draft penalties, and while the Yankees would still have to pay a 110% tax on his salary, that money is worth it if you can win the AL East and make a deep playoff run. You only get one guaranteed year with Juan Soto; it’s time to act on that reality.

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