Jordan Montgomery Faces a Lose-Lose Situation with Looming Player Option

Jordan Montgomery would be foolish to turn down his $22.5 million option, but getting out of Arizona could be more valuable in the long run.

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)

Jordan Montgomery’s tenure with the Diamondbacks has been an unmitigated disaster from the start. After beating the D-Backs as a member of the World Series champion Texas Rangers in 2023, Montgomery was a late addition to Arizona signed during spring training in 2024.

Montgomery would later fire his agent Scott Boras after inking the two-year, $47.5 million deal in free agency, as he rightfully felt that money was left on the table by waiting too long on a market that did not develop the way Boras anticipated.

The 31-year-old had earned himself a nice payday after being the Game 1 starter for the rangers in the playoffs, pitching to a 3.00 ERA in 30 pivotal innings for Texas.

His success was not just reserved to the postseason, as Montgomery pitched to a 3.20 ERA in 32 starts and 188 2/3 innings pitched in the regular season. This marked his third-consecutive year where he pitched to a sub 4.00 ERA, made 30+ starts and eclipsed 155 innings pitched.

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A durable starting pitcher who proved he could perform on the biggest stage, Montgomery should have signed a contract that set him up for years to come, inking a deal that was at least three years long if not more. Instead, he had to settle for a prove-it deal. And prove it he did not.

Disaster Season in Desert

After posting a career-year in 2023, Montgomery went to the other extreme and had the worst season of his career in 2024. The left-hander pitched to a 6.23 ERA, over just 117 innings pitched.

Outside of his years dealing with Tommy John surgery from 2018 through 2020, this marked the first time in his career that Mongtomery did not exceed 155 innings pitched. It was also the first time he had ever finished with an ERA north of 4.00, and where he did not pitch exclusively out of the starting rotation.

With the D-Backs making a playoff push in the second half, Montgomery was moved out of the rotation at the end of August and was not used entirely over the final week of the season.

Recently, Diamondbacks owner Ken Kendrick made some inflammatory comments about Montgomery during a local radio appearance on The Burns & Gambo Show, where he took the blame for signing Montgomery in the first place.

“Looking back, in hindsight, a horrible decision to have invested that money in a guy that performed as poorly as he did,” he said. “It was our biggest mistake this season from a talent standpoint. And I’m the perpetrator of that.”

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Nobody can blame Kendrick for stating the obvious when it comes to Montgomery’s performance but making those comments publicly is what is very fascinating in this situation.

Montgomery has a very expensive player option that is looming over Kendrick and his payroll for the 2025 season. It is much easier to spend money coming off a World Series run, than it is coming of a season that ended via tiebreaker in a heavily-contested Wild Card race.

Will Montgomery Stay or Go?

Between his struggles pitching in Arizona, where he had a 6.90 ERA (compared to a 5.50 ERA on the road), and now knowing he is not really welcome by ownership heading into 2025, Montgomery has a tough decision to make regarding his future.

There is not a world where Montgomery will make $22.5 million to pitch in 2025 unless he accepts his player option with the Diamondbacks. With that said, if Arizona is just a horrible situation for him to find success, Montgomery could seek refuge on a prove-it deal with the team of his choosing in free agency.

Leaving money on the table is something athletes rarely do in sports, and rightfully so. Montgomery earned at the very least the $47.5 million he was guaranteed on this contract, and really should have signed a longer deal that would have far-exceeded it in terms of total guaranteed money.

Montgomery may not be a $20+ million pitcher moving forward, but a left-handed starter who can take the ball every fifth day should still command a salary of at least $14 million annually based on what we have seen in the market the last few years.

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If Montgomery is going to get another chance at signing a deal that spans three-to-four years, he is going to have to bounce back in a big way in 2025, and that might not happen in Arizona.

When you consider the gravity of a $22.5 million contract for a small market team like the D-Backs, it becomes a bit more pointed when he revisit owner Ken Kendrick’s comments about Montgomery.

Montgomery was the D-Backs highest-paid player in 2024 and would be so again in 2025. Their second-highest paid player in both instances is Eduardo Rodriguez, a fellow left-handed starter who did not live up to the billing this season.

Rodriguez’s lack of production could be tied more to health than anything else, as he did not make a start until August, finishing the year with just 10 starts and a career-low 50 innings pitched. E-Rod struggled in those starts as well, pitching to a 5.04 ERA.

Looking at the offensive additions the D-Backs made last offseason, they largely hit across the board with Joc Pederson, Randal Grichuk, and Eugenio Suarez all having solid years. The two big pitching acquisitions of Montgomery and Rodriguez did not go nearly as well.

When you consider this team was a single win away from back-to-back playoff appearances for just the second time in franchise history, it might not be overstated to say that the signings of Rodriguez and Montgomery cratered their season.

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With Rodriguez locked into a four-year, $80 million deal, you don’t hear Kendrick making any comments about a pitcher they are clearly stuck with for the foreseeable future. They will hope that Rodriguez bounces back, and his track record suggests he absolutely will.

The same can be said about Montgomery’s track record, and the most likely scenario is still that he accepts his player option and gives it another go in Arizona in 2025. There is a world where what failed to work for the D-Backs in 2024 will become the foundation of a great rotation in 2025.

Still, until some positive results come in, Montgomery’s place in Arizona is going to be very tenuous, as they have little stacked to his future beyond next season. Whether it is with the D-Backs, or if he decides to test the free agent waters to bounce back elsewhere, hopefully, the 2025 campaign will bring more success to Montgomery and he can get his career back on track.