Jordan Montgomery may be the biggest victim of Scott Boras’ offseason negotiations last year and Monty isn’t holding back about it.

Arizona Diamondbacks v Miami Marlins
Arizona Diamondbacks v Miami Marlins / Megan Briggs/GettyImages

Heading into the 2023 offseason, Jordan Montgomery was set to collect a major payday. He had been excellent with the St. Louis Cardinals early in the year, but more importantly, he dominated with the Texas Rangers during the second half and into the postseason.

In the postseason, Montgomery tossed seven shutout innings against the Rays en route to a series win. He would flash excellence again in the ALCS when he made three appearances, two starts, recording 14 innings of sub-2.00 ERA baseball.

With such a dominant stretch to end the season, including a World Series ring, Montgomery was relying on his agent, Scott Boras, to secure him the big money deal that he was looking for in free agency. Instead, Montgomery stayed unsigned late into free agency and had to settle for a one-year deal.

The lefty didn’t hold back when he discussed his agent’s handling of the situation.

“I had a Zoom call with (the Red Sox), that’s really all I know. It went good,” Montgomery said, via Mac Cerullo of the Boston Her. “I don’t know, obviously Boras kind of butchered it, so I’m just trying to move on from the offseason and try to forget it.”

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop between now and the MLB offseason

Jordan Montgomery’s free agency saga led to a terrible season

Days of waiting turned into weeks for Montgomery. Weeks turned into months and before he knew it, he was a few weeks from the 2024 season, and he hadn’t been given a contract yet.

Montgomery was looking for a multi-year extension that would pay him upwards of $100 million. When he signed his name on the dotted line, the best that Boras got him was a one year, $25 million contract with the Arizona Diamondbacks that includes a vesting option in 2025.

Montgomery wasn’t the only victim of Scott Boras’ mismanagement of offseason negotiating. Blake Snell, Matt Chapman and Cody Bellinger were also Boras clients that were expected to sign long term deals, but ended up with short term contracts deep into the signing period.

Out of the four victims here, Montgomery was the one that drew the shortest straw, though that is partially by his own doing as well. The lefty has struggled horribly this year and unless he turns it around next year, he won’t see a deal anywhere near the $100 million contract that he wanted last offseason.

Now, Scott Boras has the biggest assignment possible on his plate as we head into the 2024 offseason: Juan Soto’s potentially record-breaking deal. Soto’s deal could redeem the agent. Or it could send him further down the totem pole following 2023’s disaster of an offseason.