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Yankees Potential Free Agent Target: Jordan Montgomery

Well, well, well, we (could) meet again, Monty.

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World Series - Texas Rangers v. Arizona Diamondbacks - Game Five Photo by Rob Tringali/MLB Photos via Getty Images

Starting pitching is an area that the Yankees have really tried to focus on improving in recent years. Bringing in Carlos Rodón from the San Francisco Giants to be the No. 2 behind ace (and hopefully the future Cy Young winner) Gerrit Cole has not paid its dividends yet, and the rotation beyond was mixed throughout 2023 with multiple players hitting the injured list at different times. To wit, 12 different players started at least one game for the Yankees in 2023, with the so-so Clarke Schmidt standing as the only non-Cole pitcher to make at least 20 starts.

Luckily for the Yankees, if general manager Brian Cashman and owner Hal Steinbrenner decide that pitching is a route they want to pursue, again there are some intriguing options on the free agent market this offseason. One of those options is a very familiar face in southpaw Jordan Montgomery.

Montgomery’s development in New York and subsequent trade away is well-trodden ground by now, so we won’t belabor the point. The short version is that the 2014 draft pick underwent Tommy John surgery not long after a commendable rookie season in 2017, and after a shaky return in the COVID-shortened 2020, he was a perfectly solid (albeit not spectacular) starter from 2021 until the 2022 Trade Deadline.

After Montgomery was dealt to the St. Louis Cardinals for outfielder Harrison Bader, there was an improvement in his numbers during the second half. He racked up more fWAR in 10 fewer starts and saw a dip in his ERA from 3.69 to 3.11. But fortunately for Yankees fans, Bader mashed the ball in the postseason following a return from injury, so it felt as if Monty was just another former Yankee. The vast majority of the fanbase and his teammates loved him, but it just didn’t work out, and that’s OK. Even with the lefty’s improvements, there were better things to focus on happening in The Bronx. However, as Bader’s bat utterly collapsed in 2023, Montgomery’s left arm surged once more.

With the Cardinals at the bottom of the standings, they had no use for a lefty pitcher at the end of his contract. So, they moved him to the Texas Rangers (along with reliever Chris Stratton) for infielder Thomas Saggese, righty starter Tekoah Roby, and lefty reliever John King. To say that the trade worked out would be an understatement.

Montgomery finished the season with career-bests in ERA (3.20), FIP (3.56), and fWAR (4.3). Most of that came from his time spent with the Rangers, where he finished the regular season with a 2.79 ERA, 3.27 FIP, 3.83 xFIP, and 1.7 fWAR in 10 fewer starts than he got with the Cardinals in the 2023 season. Below are his percentile rankings for the totality of 2023:

Jordan Montgomery’s 2023 Percentile Rankings
Baseball Savant

The main difference between Montgomery’s Yankees tenure and his stints with the Cardinals and Rangers is the usage of a sinker. He went from throwing that pitch 21.9 percent of the time in 2021 to 34.6 percent in 2022 and then 42.6 percent in 2023. His changeup and curveball usage were the same, but with his sinker usage increasing, it meant his fastball and cutter were used much less.

So, it wasn’t necessarily that Montgomery was a “better pitcher” in terms of talent after leaving the Yankees. However, his coaches in St. Louis and Texas knew how to use him properly and knew what he should throw to get better results. Matt Blake has generally done a good job in New York, but Monty’s development elsewhere is an unfortunate mark on the pitching coach’s record.

Where Montgomery made his name, though, and where he’s getting his value in free agency, was the postseason. He started five games (pitched in six total) and finished with a 2.90 ERA. His FIP (3.90) and xFIP (4.51) were higher than his ERA would suggest, but nonetheless, he was one of the most valuable pitchers on the Rangers staff in their march to the first World Series title in franchise history. Without him and rotationmate (and fellow former Yankee) Nathan Eovaldi, it’s unlikely that Texas wins it all.

Montgomery’s best performance came in the American League Championship Series, where he posted a 2-0 record with a 1.29 ERA and a singular relief appearance against the Astros. He was utterly fantastic and put himself in the running as a top free-agent pitcher for teams to pursue.

So, where do the Yankees fall in all of this? Free agency is, ultimately, up to the players and the teams. If the Yankees want to devote money to going after pitching, then Montgomery is a good option, but whether he would want to come back to The Bronx is a whole other question. There have been rumors that he would rather pitch for an organization where he has a history, so each of New York, St. Louis, and Texas would be in the mix. Rumors are, of course, just that, and if someone else makes a big enough offer, money talks.

It also feels as if the Yankees also have their sights set on other pursuits, such as a potential deal for Juan Soto to fill the left-field hole and another pitcher by the name of Yoshinobu Yamamoto. Unless Steinbrenner overrules him, Cashman would also have to be willing to eat his words from mid-2022 about Montgomery not being a playoff starter.

The Athletic is predicting a five-year, $127 million deal for Montgomery, so if things don’t work out on some of the other fronts, then that might be a worthwhile option. However, as of now, it’s hard to picture the two parties coming together on a deal that brings the lefty back to New York.