Brian Cashman, Hal Steinbrenner must be dragged for Jordan Montgomery evaluation

Never let them hear the end of this.
Championship Series - Houston Astros v Texas Rangers - Game Five
Championship Series - Houston Astros v Texas Rangers - Game Five / Carmen Mandato/GettyImages

Jordan Montgomery, armed with an effective fastball and a "Death Ball" curve, toed the rubber while Game 7 of the ALCS -- in Houston -- hung in the balance. Weeks before free agency, the most pivotal earning period of his life to date, he forsook a throw day and demanded the ball. For the third time in as many outings, he managed to keep the powerhouse Astros at bay, something an entire generation of Yankees pitchers has failed to do (Montgomery, in pinstripes, was never given the chance).

Every Yankee fan on earth feels fantastic for Montgomery, whose arsenal was handled better by Mike Maddux than by Matt Blake and the Yankees' upper management group. But every Yankee fan on earth also demands the answer to a very simple and straightforward question. What led you to believe Montgomery wouldn't be an effective October pitcher, and what went wrong in the process of that evaluation?

Honestly? That question should be Hal Steinbrenner's entire audit. And it should most definitely be the first question out of whichever reporter's lips get the first crack.

Yankees should be asked every single day why they couldn't see what Jordan Montgomery could become

This isn't even meant as a flame job of the Harrison Bader trade. If we're going to torch Brian Cashman daily for opting out of taking risks, then we have to commend him for making an uncomfortable trade to acquire someone who was a postseason hero in 2022 (and was, uh, not very effective in 2023). It wasn't the swap that stung. It was the evaluation, all the dirty details that came out after the deed was done that made it clear the Yankees believed Montgomery was a non-entity. Someone who couldn't be polished. Someone whose ceiling was "not interesting."

That was very, very incorrect -- and, worst of all, it only took about a week for the Cardinals to point him in the right direction last summer.

Once Maddux got his hands on Montgomery, he encouraged him to throw the fastball the Yankees had discarded in favor of a botched cutter. Always effective (Montgomery never had an ERA higher than 3.83 in a full season with the Yankees!), the lefty leveled up, shaving a half-run off his mark in '22 after arriving in St. Louis. Now, with the Rangers, he's proven beyond a doubt that his "sh*t works" in the playoffs, posting a 1.29 ERA in 14 innings against the dreaded Astros.

"Whoa," said the remaining Yankees. "You can complete more than three innings against those guys?"

The Yankees' not-so-dirty secret is that they were in talks to acquire Pablo López last summer, and might not have included Montgomery in a best-case-scenario playoff rotation featuring Gerrit Cole, Nestor Cortes, Luis Severino and López. But best-case-scenarios rarely materialize. At the time, we thought the Yankees were sacrificing crucial depth, but not a star, when they sent Montgomery packing.

As it turns out, we didn't know what they had because they didn't either. And it's beyond time to find out what got lost in translation.