The Yankees would like to get back together with their former starting pitcher

Jordan Montgomery, a longtime mainstay of the rotation, may be coming back to the Yankees, according to Jon Heyman of the New York Post.

Heyman notes that “the Yankees have been particular about rotation targets,” suggesting that the team may be considering something more than simple due diligence when considering Montgomery as a potential offseason addition. The Yankees’ pitching wishlist has been linked to players like Yoshinobu Yamamoto, Frankie Montas, Yariel Rodriguez, and Aaron Nola (prior to his re-signing with the Phillies). Given that Ohtani won’t be able to pitch in 2024, it’s probably safe to assume the Bronx Bombers are at least somewhat interested in Ohtani.

Given that Montgomery began his professional career in the Yankees after being selected in the fourth round of the 2014 draft, he is undoubtedly a known quantity for the team. After making his major league debut in 2017, Montgomery went on to establish himself as a reliable and somewhat underappreciated part of the starting five with his 502 2/3 innings pitched for New York, with a 3.94 ERA, 22.68% strikeout rate, and 6.93% walk rate.

Harrison Bader came from St. Louis in a one-for-one trade, and aside from a tremendous power surge during the Yankees’ 2022 playoff run, Bader’s time in New York was disappointing. The outfielder played in just 98 regular-season games due to injuries, and before the Yankees placed him on waivers this past August, he hit.237/.274/.353 over 359 plate appearances. Despite this success, the left-hander was dealt to the Cardinals at the 2022 trade deadline in a move that has since become infamous in the Bronx.

Montgomery’s fame (and free-agent cost) kept getting bigger in the interim. Although Montgomery was once again traded at the deadline, this time to the Rangers, due to the Cardinals’ internal issues, he pitched well for St. Louis for the remainder of 2022 and into 2023. From then on, Montgomery emerged as a major player in the Rangers’ World Series run. The left-hander finished the regular season with a 2.79 ERA over 67 2/3 innings, which was enough to push Texas into the postseason. In the postseason, he produced a 2.90 ERA over 31 innings.

Montgomery is projected to sign a six-year, $150 million contract with MLBTR, which placed him sixth on our ranking of the top 50 free agents for the winter. Although Montgomery is six months older and has had a Tommy John surgery in the past, it is very feasible that he will surpass our forecast as well. Nola earned the same projection and signed a seven-year, $172M deal with Philadelphia. But because of the midseason deal, Montgomery was not eligible for the qualifying offer, so if he signs, the team signing him would not have to give up any international pool money or draft picks in exchange.

The Yankees, who exceeded the luxury tax in the previous season and would have to pay a harsher penalty of two choices and $1 million in international bonus money if they signed any qualified free agent, would surely be interested in this. The Bombers are open to signing free agents who turn down QO, as evidenced by their interest in players like Nola, Ohtani, or Cody Bellinger. However, it’s reasonable to surmise that the Yankees might only be prepared to make the risk for one such player. Bellinger, for example, might be given more consideration since the Yankees need to improve their batting, but they could also consider any of a number of non-QO pitchers, including elite players like Yamamoto or Montgomery.

It’s reasonable to wonder if Montgomery’s history with the Yankees will stand in the way of any talks. Naturally, general manager Brian Cashman would prefer to go back and redo the Bader deal. Given that his doubts about Montgomery’s ability to start in the postseason have been disproven, what better way to make amends publicly than to give him a $150 million contract? It’s possible that Montgomery will consider it a minor setback and agree to go back to the Bronx to settle some outstanding matters.

On the other hand, it seems possible that Montgomery simply wants to move on from an organization that once considered him expendable, and would prefer to join either a new team altogether or one of his other former clubs in Texas or St. Louis.