Almost seven months after he signed with the Arizona Diamondbacks, Jordan Montgomery's baseball team faced the Boston Red Sox at Fenway Park. Montgomery, himself, did not appear.
The lefty sought a pricey, long-term deal during the 2023-24 offseason and was not lucky enough to be signed. He insisted on playing for a winning club, and while the Sox looked like they could be one for a while, the Diamondbacks have taken off at a run after the All-Star break. Montgomery, however, has played a much smaller-than-expected role in their plans.
The veteran has been moved to the bullpen after a shaky start to his age-31 slate, and it could prevent him from ever signing the long, lucrative contract he hoped for over the winter. He's posted a 6.44 ERA over 95 innings across 19 starts — a stark increase from his career-3.68 ERA metric after 2023.
It's been reported that the Red Sox pursued Montgomery and made him a contract offer last offseason. The pitcher told Mac Cerullo of The Boston Herald that he never received an offer from the Red Sox and offered some choice words on his relationship with his former agent, Scott Boras. Less than two weeks after he signed his one-year, $25 million deal with the Diamondbacks, the lefty switched his representation from Boras to two agents at Wasserman.
“I don’t know, obviously Boras kind of butchered it,” Montgomery said. “So I’m just trying to move on from the offseason and try to forget it."
Jordan Montgomery speaks out on experience with former agent Scott Boras during Diamondbacks-Red Sox series
.@ErikKratz31 on Jordan Montgomery saying Scott Boras "butchered" his free agency:
— Foul Territory (@FoulTerritoryTV) August 26, 2024
"When you are signed on with Boras, you're looking for the top dollar. Teams know that, Boras knows that and you know that. This is how the landscape is." pic.twitter.com/ANu8feJdh2
Montgomery added that he and his wife loved the city of Boston and that he admires the Red Sox's fanbase, but something went awry between Boras and Boston's front office during their negotiations.
Boras is infamous in the baseball community and beyond for the prices attached to his clients. Montgomery, Blake Snell, Matt Chapman and Cody Bellinger all sought expensive deals with Boras as their representation this offseason — Snell, Chapman and Bellinger have all fared better with their new clubs than Montgomery, who will be a free agent again after his rough year.
It was clear from the outside that Boras overvalued Montgomery as a free agent. The two sought a deal similar to the ones signed by Carlos Rodón and Aaron Nola for the lefty — Rodón signed with the Yankees for six years at $162 million and Nola signed a seven-year, $172 million deal with the Phillies.
The three hurlers have similar stats, but not similar accolades. Rodón is a two-time All-Star and Cy Young candidate. Nola has received one All-Star nod, but earned Cy Young votes three times. Montgomery secured Rookie of the Year contention in 2017, but no other in-season accolades for his body of work.
The missed contract in the 2023-24 offseason likely changed the trajectory of Montgomery's career. The reigning World Series champion helped carry the Texas Rangers' rotation throughout the postseason, but it's possible front offices across MLB saw those career-best numbers as a fluke.
But Montgomery knew when he signed with Boras that the agent would try to get him signed with a new club for the maximum possible amount. Teams have the final say on whether or not to spend their money, and they elected not to spend on Montgomery, which, unfortunately for the veteran, ended up being a good thing for the Red Sox.