The Yankees seem to be considering a reunion with former rotation stalwart Jordan Montgomery, according to the New York Post’s Jon Heyman. The club has been “looking at” Montgomery as a possible offseason signing, and it appears to be slightly more than just due diligence, as Heyman writes that “the Yankees have been particular about rotation targets.” Previous reports have linked such arms as Yoshinobu Yamamoto, Frankie Montas, Yariel Rodriguez, and (before he re-signed with the Phillies) Aaron Nola to the Yankees’ pitching wishlist, and it’s probably safe to assume the Bronx Bombers have some level of interest in Shohei Ohtani even though he won’t be able to pitch in 2024.
Obviously Montgomery is a known quantity for the Yankees, having started his pro career in the pinstripes after being drafted in the fourth round in 2014. Debuting in the majors in 2017, Montgomery posted a 3.94 ERA, 22.68% strikeout rate, and 6.93% walk rate over his 502 2/3 innings with New York, establishing himself as a solid and even underrated member of the starting five.
Despite this success, the left-hander was dealt to the Cardinals at the 2022 trade deadline in a move that since become infamous in the Bronx. Harrison Bader came from St. Louis in the one-for-one-swap, and apart from a spectacular power surge during the Yankees’ 2022 playoff run, Bader’s time in New York was a disappointment. The outfielder played in only 98 regular season games due to injuries, and hit .237/.274/.353 over 359 plate appearances before the Yankees put him on waivers this past August.
Meanwhile, Montgomery’s star (and free agent price tag) only continued to rise. He pitched well for St. Louis during the rest of the 2022 season and into 2023, though the Cardinals’ own struggles saw Montgomery again on the move at the deadline, this time to the Rangers. From there, Montgomery became one of the key factors of the Rangers’ World Series run — he posted a 2.79 ERA over 67 2/3 innings in the regular season just to help Texas get into the playoffs, and the lefty then had a 2.90 ERA over 31 postseason frames.
MLBTR ranked Montgomery sixth on our list of the winter’s top 50 free agents, projecting him for a six-year, $150MM contract. Nola received the same projection and landed a seven-year, $172MM deal from Philadelphia, so it is quite possible Montgomery might also beat our prediction even though he is six months older and has a past Tommy John surgery on his record. However, Montgomery wasn’t eligible for the qualifying offer due to the midseason trade, so a team that signs him wouldn’t have to surrender any draft picks or international pool money as compensation.
This is undoubtedly of interest to a Yankees team that surpassed the luxury tax last year, and thus would pay the higher penalty of two picks and $1MM of int’l bonus money for signing any qualified free agent. New York’s interest in such players as Nola, Ohtani, or Cody Bellinger indicates that the Bombers are open to signing QO-rejecting free agents, though it’s fair to speculate that the Yankees might be willing to take the plunge for only one such player. For instance, Bellinger might be a bit of a priority since hitting is a greater need for the Yankees, but they could then also look one of many non-QO pitchers, including top-tier names like Yamamoto or Montgomery.
It is fair to speculate whether or not the past history with Montgomery and the Yankees is an obstacle in any negotiations. Naturally GM Brian Cashman would love to have a do-over of the Bader trade, and since his concerns over Montgomery’s viability as a postseason starter have now been firmly proven wrong, what better public mea culpa than a $150MM contract? Montgomery might see it as water under the bridge and be willing to return to complete some unfinished business in the Bronx. 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.