It was indeed an offseason to forget for Jordan Montgomery, who tasked agent Scott Boras with getting him the best deal possible on the open market. The former New York Yankees pitcher went on an unforgettable run in 2023 to help the Texas Rangers capture their first ever World Series, suggesting that his contract year was going to get him paid.

Unfortunately, the suitors did not line up for Montgomery, who ended up settling for a one-year, $25 million contract with the Arizona Diamondbacks. He signed late, so he missed all of spring training and got a delayed start to his 2024 campaign.

The result? A 6.44 ERA, 4.57 FIP and 1.67 WHIP in 19 starts. Terrible. Imagine how much better Arizona would be if he was just barely serviceable?

This past weekend, Montgomery was in Boston as the D-backs took on the Red Sox (and swept them, yay!). As everybody knows, the Red Sox were among the teams pursuing Montgomery, but not at the rumored price tag of six years and $160-plus million. Montgomery’s wife was serving a medical residency in Boston, so it felt like a perfect match, but it didn’t work out.

When asked about his free agency by the Boston media, Montgomery, who ended up firing Boras, threw his former agent under the bus with his answers.

Jordan Montgomery flaming Scott Boras shows Yankees reunion was never possible

That’s some savagery. Boras definitely needs to shoulder blame for that poor of a showing, but Montgomery’s career body of work definitely didn’t align with the rumored contract demands. For example, he wasn’t getting paid more than two-time Cy Young winner Blake Snell, and Carlos Rodón’s six-year, $162 million contract was a poor comp because of Rodón’s previous ace-like profile. Monty, for as good as he is, isn’t known for his top-of-the-rotation presence.

And speaking of Rodón’s $162 million, the Yankees felt rather ripped off by that number they agreed to with Boras. That’s why they reportedly went lower ($150 million) for Snell this past offseason. And that’s probably reportedly why nothing ever came to fruition with Montgomery.

In the latter stages of his free agency, the Yankees entered the rumor mill, but the situation remained complicated because of Montgomery’s desires and New York’s payroll implications.

Based on what Montgomery said about Boras, too, a Yankees reunion couldn’t ever have realistically been on the table. If a one-year deal with a player option was viewed as rock bottom for Monty, what could have Boras possibly been speaking with Brian Cashman about? The left-hander definitely wasn’t signing a one-year deal with the team that ditched him at the 2022 trade deadline, nor was he taking a cheaper multi-year contract to bend to the team’s luxury tax needs.

Perhaps that could change this coming offseason when the Yankees free up some cash, with Boras out of Montgomery’s picture, but we can’t say we’re counting on it. What’s done is done. And the famous duo of Boras and Cashman is to blame (with Juan Soto’s free agency looming).