It's no secret that Jordan Montgomery was one of the premier starting pitchers available in free agency last winter. Yet, he didn't sign until deep into spring training with the Arizona Diamondbacks. That lack of innings in Cactus League action hurt the big lefty, who has been downright poor in 2024 after such a dominant campaign en route to a World Series title with the St. Louis Cardinals and Texas Rangers in 2023.

Montgomery is represented by Scott Boras, one of the most powerful sports agents in the world. But, Boras clearly didn't do his best at finding his client a team early in the offseason. The Boston Red Sox were one ball club very interested in Montgomery and it appears the feeling was mutual, as he pointed out recently in an interview with Mac Cerullo of the Boston Herald. The starter also made it clear: Boras messed up his free agency:

“I had a Zoom call with (the Red Sox), that’s really all I know. It went good,” Jordan Montgomery said. “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.”

Montgomery wasn't alone. Cody Bellinger, Matt Chapman, and Blake Snell are all Boras clients as well and none of them signed early, which meant none received the type of contract they really deserved. Snell struggled immensely to begin the season because he didn't take the mound in spring training, but he's since figured it out for the San Francisco Giants.

Difficult season for Jordan Montgomery

While there's no excuse at this point to still be struggling, Montgomery has been terrible in '24. He's 8-6 with a 6.44 ERA in 19 starts, striking out 67 hitters in 95 innings. That's the worst ERA of his career. In comparison, the left-hander owned a 2.79 ERA in 11 appearances with the Rangers after they acquired him at the trade deadline. Montgomery then absolutely shoved in the playoffs, especially in the ALCS against the Houston Astros, posting a 1.29 ERA.

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Sure, there's no question Boras did butcher the entire situation for Montgomery, but it's clearly just a down season for him. With the D-Backs in the playoff race, he could have the chance to redeem himself when it matters most.