Yankees Should Not Pursue Jordan Montgomery This Off-Season

By Derek McAdam

October 18, 2023

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The MLB playoffs have now reached the Championship series stage, and two ex-Yankees have emerged as important players for the Texas Rangers. As many Yankee fans know, the two players are Jordan Montgomery and Nathan Eovaldi. Montgomery has delivered two solid performances for the Rangers, including the shutout performance in Game 1 of the ALCS, while Eovaldi had a solid performance in Game 2, putting the Rangers up in the series against the Houston Astros 2-0.

Montgomery’s success has had many Yankee fans fuming over Brian Cashman’s decision last summer to trade the southpaw in a straight up trade to St. Louis for Harrison Bader. While the Yankees were attempting to acquire a high-end center fielder, which was a position of need, Bader ultimately came to the Bronx with one major issue. Bader is one of the best center fielders in the game, defensively, but has had his share of injuries. In fact, he was on the IL when the Yankees acquired him and served two additional IL stints while with the Yankees before being placed on waivers late into the 2023 season.

Sure, Bader was arguably the best Yankee during the 2022 post-season, hitting five home runs in the playoffs and providing fantastic defense in center field. And while he had a decent 2023 season, he was plagued with injuries and the Yankees ultimately gave him up for nothing. Meanwhile, Montgomery has taken the reigns of the Rangers’ starting rotation and is in line to receive a large contract this off-season, one much larger than he was expected to receive just a couple of months ago.

While I have liked Montgomery since he came into the league in 2017 with the Yankees, as he has been one of the best pitching prospects that the Yankees have developed in their farm system in recent times, the Yankees cannot bring Montgomery back to the Bronx, unless they could sign him to a very team-friendly deal, which is unlikely to happen.

The Yankees are in a position this off-season where they are going to sign or trade for a starting pitcher, even if that means re-signing Luis Severino or Frankie Montas. The Yankees currently have Gerrit Cole, Clarke Schmidt, Michael King, and Nestor Cortes Jr. going into next season as four definite starters, but the fifth spot is up for grabs, and I would argue that Cortes’ spot isn’t even guaranteed.

Montgomery will be 31-years-old at the end of this year, which puts him in a prime position to receive a long-term contract that may definitely surpass $100 million if he continues this solid post-season run. The Yankees already have nearly $500 million committed to Cole and Rodon, so it seems unlikely that Cashman would want to add a third $100 million deal to the rotation unless it is Yoshinobu Yamamoto, the star pitcher from Japan.

If the Yankees decide to make a serious offer for Montgomery, the good news is that they are already aware of his ability to pitch at Yankee Stadium under the bright lights. He’s never been a shut-down pitcher, but he has proven that he can be a solid No. 2 or No. 3 pitcher in nearly any rotation. However, with the uncertainty of how Rodon is going to play out long-term, I don’t think this is a signing that the Yankees should pursue.

With Yamamoto, he would be expected to fill right in as the No. 2 starter behind Cole, shifting Rodon down to the No. 3 role, at best. Although it is too early to say if he will be “elite” in the big leagues, he is going to get a contract that says he is. Montgomery is going to be a very nice contract, but it won’t be what an “elite” pitcher in the game will get. Sure, the Yankees know exactly what they’re getting in Montgomery, but it seems pretty obvious as to what his ceiling is. Yamamoto is going to have that higher ceiling once he comes over to the Majors, but if he gets there is another question.

By no means am I advocating that the Yankees sign Yamamoto, because I don’t think they should sign any big contract this off-season, but for the money that these two players will get, Yamamoto might be the better bargain for the Yankees. The Yankees need to become a younger team, and Yamamoto being 25-years old is much younger than a 31-year old, at least in the sports world.

One other aspect to mention is whether or not Montgomery still has hard feelings towards the Yankees. Would he even want to come back to an organization that traded him, even though he was the most consistent Yankee in the 2022 season? I doubt Montgomery would refuse to sign simply because of that reason, but I’m sure he would need to iron some things out with Cashman before any contract was signed.

I must reiterate that I don’t think the Yankees should pass on Montgomery because of his ability. If the Yankees can get Montgomery at a good price, I think they should go for it. However, Montgomery is not going to come at a “good price” as long as he continues to pitch well in the post-season. And that’s great for him. I hope he can get as much money as possible in free agency.

However, the Yankees should take the route of not spending money on free agents just because it’s available. Whether they do that or not is another story, but they should considering passing on Montgomery this off-season.