The Jordan Montgomery era with the Arizona Diamondbacks might be the worst Free Agent disasters in MLB history

Well, it’s official: the Jordan Montgomery-Arizona Diamondbacks “partnership” can now be filed under catastrophic baseball decisions.

The lefty who once helped pitch Texas to a World Series title will now miss the entire 2025 season after it was revealed he needs Tommy John surgery. And for the D-backs, it marks the end of one of the more brutal signings in recent MLB history.

Jordan Montgomery went from Postseason Hero to Free Agent Disasterclass

Jordan Montgomery was coming off a stellar 2023, splitting time between the Cardinals and Rangers and dominating down the stretch for Texas. All things considered, it should have been the perfect setup for a fat payday in free agency.

Instead, Scott Boras tried to run the clock out on the league—again—and it backfired. Montgomery lingered on the market until late March, signing a one-year, $25 million deal with Arizona that included a vesting option for 2025.

It was a short-term bet that required Jordan Montgomery to hit the ground running and honestly, it shouldn’t have been a surprise that he never did.

Montgomery was behind the rest of the league, never found his rhythm, and the Diamondbacks wound up shifting him to the bullpen midseason because they were stuck with a guy who couldn’t command the zone, couldn’t stay on schedule, and suddenly wasn’t the reliable innings-eater he’d been just one year prior.

Disaster from Start to Finish

By the end of the season, D-backs owner Ken Kendrick was openly calling the Montgomery contract the worst decision of the year. And that was before the vesting option triggered for 2025 and locked Arizona into another $25 million. They’ve reportedly been shopping him all offseason like a half-used snowblower in August.

And now this.

Just days before Opening Day, Montgomery was getting hugs in the dugout—classic “you’ve been traded” energy—only for the baseball gods to swerve the storyline and hit us with Tommy John surgery. Now he’s not getting traded. He’s not pitching at all. And the Diamondbacks are going to pay $25 million for a guy who won’t throw a single pitch in 2025.

Jordan Montgomery will have Tommy John surgery and miss the 2025 season pic.twitter.com/9wA5GcCs32

— Barstool Baseball (@StoolBaseball) March 25, 2025

Boras, Blunders, and Blame

This whole saga is a masterclass in how waiting out the market doesn’t always mean leverage. Montgomery went from World Series hero to late-spring pickup to bullpen arm to injured liability. Boras, by the way, got fired by Monty not long after the Arizona deal was signed.

Can’t say that was undeserved.

It’s fair to wonder whether starting the season cold in 2024 led to this. Jordan Montgomery never looked fully ready. His mechanics were off, and maybe his arm never caught up. Who knows what a normal offseason and spring training would have done for his long-term health.

But here we are.

What’s Next?

Montgomery still gets his money (baseball contracts are fully guaranteed, after all), but the Diamondbacks might not be so lucky. If they didn’t insure the deal—which, considering the late signing, they might not have—then this is a straight $25 million gut punch with no refund.

We’ll have to wait and see if Jordan Montgomery gets another shot in 2026, but it’ll be with a long rehab ahead and a big asterisk on his recent resume.

As for the Diamondbacks? They were riding high after a surprise 2023 playoff run, and now they’re eating $25 million and praying their rotation holds up without the guy they signed to stabilize it. This one’s gonna sting for a long time.

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