It’s no secret that Jordan Montgomery was one of the best starting pitchers available as a free agent last winter, yet he didn’t sign with the Arizona Diamondbacks until midway through spring training. That lack of innings in the Cactus League hurt the big left-hander, who was notably weak after such a dominant season en route to a World Series title with the St. Louis Cardinals and Texas Rangers in 2024.

Montgomery is represented by Scott Boras, one of the most powerful sports agents in the world. But Boras clearly didn’t do his best to find his client a team early in the offseason. The Boston Red Sox were a ballclub very interested in Montgomery, and it seems the feeling is mutual, as he pointed out in a recent interview with Mac Cerullo of the Boston Herald. The starter also clarified that Boras messed up his free agency:

“I had a Zoom call with (the Red Sox), that’s really all I know. It went well,” Jordan Montgomery said. “I don’t know, obviously Boras kind of messed it up, so I’m just trying to put the offseason behind me and forget about it.”

Montgomery wasn’t alone. Cody Bellinger, Matt Chapman and Blake Snell are also Boras clients and none of them signed early, meaning none got the contract they truly deserved. Snell struggled a lot early in the season because he wasn’t on 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 for still struggling at this point, Montgomery has been terrible in 2024. He’s 8-6 with a 6.44 ERA in 19 starts and has struck out 67 hitters in 95 innings. That’s the worst ERA of his career. For comparison, the left-hander had a 2.79 ERA in 11 appearances with the Rangers after they signed him at the trade deadline. Montgomery then gave it his all in the playoffs, particularly in the ALCS against the Houston Astros, posting a 1.29 ERA.

Sure, there’s no doubt that Boras messed up the whole situation for Montgomery, but it’s clearly just one bad season for him. With the D-backs in the race for the playoffs, he might have a chance to redeem himself when it matters most.