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At the end of the relative snoozefest that was this offseason, super agent Scott Boras seemed to be losing his signature touch. He was tasked with getting five of last season's biggest free agents their corresponding big contracts, but all five — Blake Snell, Matt Chapman, Cody Bellinger, Jordan Montgomery, and JD Martinez — had to settle for one-year (or virtually one-year) deals.
Their free agencies should've been the time to milk every last dime out of teams and capitalize on great 2023 seasons. Among them was a Cy Young winner (Snell), Gold Glover (Chapman), Silver Slugger (Bellinger), World Series champion (Montgomery), and All-Star (Martinez), who were expecting to rake in money this offseason. Instead, they were underwhelmed and may have squandered their opportunities.
Montgomery clearly wasn't happy with his outcome, because he reportedly fired Boras in favor of Wasserman agents Joel Wolfe and Nick Chanock, the latter of whom has more than a few connections to the Dodgers that should have LA looking straight at Montgomery when the season is over.
LHP Jordan Montgomery has hired Wasserman’s Joel Wolfe & Nick Chanock as his agents, per sources.
— Kiley McDaniel (@kileymcd) April 11, 2024
Montgomery was one of the Boras Four, who were unsigned late into free agency.
I projected he would get 5 yrs, $106M and he eventually signed for 1 yr, $25M w/Arizona on March 26.
Jordan Montgomery drops Scott Boras for Yoshinobu Yamamoto, Tyler Glasnow's agent
According to Forbes, Wolfe has negotiated for $1.2 billion for his clients as of November 2022, who include Nolan Arenado, Giancarlo Stanton, and Yu Darvish. However, that figure is definitely higher in 2024, as he also represents the Dodgers' very own Yoshinobu Yamamoto and Tyler Glasnow, who got $325 million and $136.5 million for 10 and five years respectively this offseason.
Although the Dodgers didn't have to face him in the postseason, Montgomery was an absolute menace to hitters last year during the Rangers' World Series run. He's yet to make a start with the Diamondbacks — thanks to Boras' stalling, he signed a day into the regular season and needs to make up for time he didn't get at spring training — but if things shake out the same way they did last year and the Dodgers and Diamondbacks meet again in the postseason, he seems like the kind of guy you'd rather have on your team in October.
Before signing, Montgomery set off a few alarms when he unfollowed the Rangers on Instagram but continued to follow the Dodgers. If he has any affinity for LA at all, maybe he should consider coming over next year. At least he'll know that the Dodgers would be willing to pay him what he's worth, and will gladly share a hearty laugh over Scott Boras not being present any longer.