Could the Arizona Diamondbacks Release Jordan Montgomery?

Due to a vesting option in Jordan Montgomery's contract, the Arizona Diamondbacks have a tough decision to make on his role moving forward.

PHOENIX, ARIZONA - JUNE 05: Jordan Montgomery #52 of the Arizona Diamondbacks delivers a pitch against the San Francisco Giants at Chase Field on June 05, 2024 in Phoenix, Arizona. (Photo by Norm Hall/Getty Images)

When the Arizona Diamondbacks signed Jordan Montgomery at the 11th hour before the start of the season, many looked at it as the move that would put them over the top.

The 31-year-old left-hander was coming off an outstanding postseason run, which saw his Texas Rangers beat the Diamondbacks in the World Series. After watching him in the other dugout, the Diamondbacks hoped that Montgomery could bring the same level of stability to the middle of their rotation, to help them get through the long season and into playoff position.

Considering the fact that he was coming off three-straight years pitching to a sub 4.00 ERA, there were few pitchers who looked like a safer bet in free agency. When they signed him to a one-plus-one deal, the consensus was that it was a great value contract.

So great in fact, that Montgomery quickly fired his agent, Scott Boras, after putting pen to paper on the deal. Now nine starts into his tenure with Arizona, a bad situation has turned into a living nightmare for Montgomery. He has pitched to a 6.80 ERA and was literally booed off the mount by Diamondbacks fans his last start.

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This came after giving up six earned runs for his second-straight start and for the third time this season. Montgomery only had three starts across all of last year where he gave up six or more earned run.

To make matters worse, that same contract he fired Boras over is potentially going to lead to Montgomery being put in a very bad position before his next scheduled start.

A Bad Contract Keeps Getting Worse

Jordan Montgomery should fire Scott Boras again because the first time was not enough.

When Montgomery hit the market, there should have been teams lining up to sign him to a multi-year deal. He had earned as much by being one of the most dependable starting pitchers in baseball over the past three years.

In 2021, years removed from a 2018 Tommy John surgery, Montgomery returned to the prominence of his rookie year back in 2017, again pitching to a sub 4.00 ERA over 150+ innings pitched.

Four years removed, Montgomery’s 2021 season was eerily similar to his 2017 season with the Yankees. In 2017, Montgomery pitched to a 3.88 ERA over 29 starts and 155 1/3 innings pitched. In 2021, Montgomery pitched to a 3.83 ERA across 30 starts and 157 1/3 innings pitched.

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In 2022, Montgomery pitched to a 3.69 ERA over 21 starts with the Yankees, before he was traded to the St. Louis Cardinals at the deadline. Montgomery spent a full calendar year with the Cardinals across two seasons, making 11 starts with them in 2022 and 21 in 2023.

During his time in St. Louis, Montgomery pitched to a 3.31 ERA. He was again dealt at the trade deadline, going to the Rangers and proving to be the biggest piece added by any team via trade when he helped lead them to a World Series.

Three-straight seasons taking the ball every fifth day, in which Montgomery improved year-over-year and showcased his ability to perform on the biggest stage. That resume was one deserving of a four or five year contract from a big league club.

Instead, after holding out for ace money that was never going to come, Boras had Montgomery take a one-year, $25 million contract, which included a $25 million conditional option for 2025.

Montgomery should not have needed to prove himself again to get a long-term deal, but that is the position his agent inadvertently put him in, leading to his ultimate dismissal after the contract was official. Now looking at the deal further, it becomes more onerous, as it could be the thing that gets him pulled from the Diamondbacks rotation.

Based on the stipulations of the contract, the Diamondbacks are already pushing up against a decision. If Montgomery makes 10 starts this season, he is guaranteed a 2025 option of $20 million. The option has escalators at 18 and 23 starts, which could increase the option to as much as $25 million.

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Montgomery has already made nine starts so far this year, so the next time he takes the mound to open a game, he will be guaranteed at least $20 million for next season. Considering how poorly he has pitched, the Diamondbacks can’t be thrilled about the idea of being tied to Montgomery for another year at that dollar amount.

This puts them in the position of either pushing Montgomery to the bullpen, or just outright releasing him to protect themselves from a a real albatross contract being on the books.

Would the Diamondbacks Really Release Him?

There aren’t a lot of executives as cold-blooded when it comes to finances than old Marlins president David Samson. This is the same executive that proudly used Derek Jeter as a pawn to get $1.2 billion out of Bruce Sherman to overpay to buy the Marlins back in 2017.

Samson has since transitioned into a career in the media, where he has worked for CBS Sports and Meadowlark Media and has a popular sports business podcast called, “Nothing Personal” With David Samson.

The title of the podcast says it all, as Samson shines a light on the less-covered aspects to the business behind baseball, and how executives and owners alike view operating issues that come up when running a club. Such as staring down the barrel of a bad contract like Montgomery’s.

What Samson knows better than anyone, is that free agent mistakes can come back to haunt you in a small market, giving him great perspective on the Montgomery situation from the prospective of the Diamondbacks.

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On his show, Samson explains how he would handle the situation on Montgomery, flatly saying that he would release Montgomery before he made his 10th start, swallowing the rest of his $25 million salary in 2024, to nullify having to pay him even a dime in 2025.

That is a cold-blooded move, but hey, “It’s business, nothing personal.”

Samson suggests that the Diamondbacks have grounds to DFA Montgomery based on his performance, which has been abysmal lately.

With that said, this is a Diamondbacks team that is coming off a World Series run, who despite their slow start, is merely a half-game out of a playoff spot. Montgomery has a track record to bet on, and the Diamondbacks are not in a position to sacrifice starter depth right now.

Arizona’s top two starters are both on the IL in Zac Gallen and Merrill Kelly, meanwhile fellow free agent acquisition Eduardo Rodriguez has not even thrown a pitch for Arizona, as he has been dealing with shoulder issue that has him on the 60-day IL.

As bad as things have gotten for Montgomery, he’s at least taking the ball right now. But if he is hurting you every time he does, what is the best move?

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One half-measure we could see the Diamondbacks do is to pitch Montgomery out of the bullpen for a bit until he gets right. This would kick the can down the road on the vesting option of hitting those 10 starts, while keeping him in the fold for this season.

The problem is that would be blatantly obvious what they are doing, especially if you essentially employed an opener on his start days to skirt around the contract.

Arizona might be in the tough position of having to bite the bullet on this Montgomery contract, although that is a decision that won’t take lightly, regardless of what they tell you publicly. Still, there was a track record that got Montgomery paid, and the Diamondbacks just have to trust that he will click back into gear sooner rather than later.

Ultimately the biggest loser in this whole situation is Montgomery. A guy that earned security in the game as a quality starting pitcher, and has completely lost that security in short order, based on circumstances that were largely out of his control.

Hopefully, Montgomery can return to form soon and prove to be an asset that helps Arizona get back over the top in this year’s playoff race.