Scott Boras Oct 7, 2023; Los Angeles, California, USA; Agent Scott Boras watches batting practice before game one of the NLDS for the 2023 MLB playoffs between the Los Angeles Dodgers and the Arizona Diamondbacks at Dodger Stadium. Mandatory Credit: Kiyoshi Mio-USA TODAY Sports

Scott Boras has cemented his legacy as arguably the greatest agent in sports history, but if you were making a highlight video of his career, this offseason would be conspicuously absent.

ESPN MLB insider Buster Olney joined the Awful Announcing Podcast this week to talk about Boras and a number of other issues with host Jessica Kleinschmidt.

When the topic turned to Boras, Olney came up with an interesting comparison for Boras, likening him to former Boston Red Sox and Chicago Cubs executive Theo Epstein, who led both clubs to World Series titles, breaking droughts of 86 and 108 years, respectively.

“To me, Scott is like Theo Epstein in terms of his prominence, he’s the greatest ever,” Olney said. “And that’s never gonna change. … Scott’s that person on the union side.”

However, just like MLB’s best players go through slumps, this offseason was not kind to Boras. The veteran agent’s most high-profile failure involved two-time Cy Young winner Blake Snell, who was expected to command a multiyear deal in the $250 million range. Instead, he signed a two-year deal last week with the San Francisco Giants for $62 million.

“There’s no question that this winter in terms of perception within the industry that (Boras) took some big hits,” Olney said. “You know, Blake Snell being the biggest one. Last week, when Blake Snell was throwing for scouts, auditioning for scouts … I tweeted out that, to ask a reigning Cy Young award winner to throw for scouts is like asking Tom Cruise to audition for community theater. Like, what is going on?”

“You’re not gonna have a better platform here than Blake Snell. And yet he winds up signing a two-year contract with a lot of money deferred. That’s insane. And you can’t paint that as anything other than a loss.”

Another one of Boras’ clients, pitcher Jordan Montgomery, had been seeking a lucrative long-term deal but settled for a one-year contract with the Arizona Diamondbacks Tuesday, just two days before the Opening Day.

Former All-Star third baseman Matt Chapman also struggled to find a new home this offseason, before signing a three-year, $54 million contract with the Giants in early March. He reportedly turned down a $125 million offer from the Toronto Blue Jays in 2023.

Outfielder Cody Bellinger, another star in the Boras stable, signed a three-year, $80 million contract with the Chicago Cubs in February that some observers thought was a bad deal for the former NL MVP.

Olney said Bellinger and even Snell’s deals point out that Boras faces such high expectations, anything short of that is viewed with disappointment.

“I don’t agree with the perception that the Cody Bellinger contract was terrible for him,” Olney said. “And some of the others, I think a lot of times Scott suffers from the fact that we have these huge projections in the fall that are put out by reporters, ‘Well, you know, Blake Snell is gonna get $220 million … and so when he gets $62 million it makes Scott look worse.

“But, I don’t think there’s any doubt that while he might have had some victories, Matt Chapman, Blake Snell, big losses.

“And I guess every now and then you get a loss, even if you’re Scott Boras, that’s interesting,” Kleinschmidt added.

In some ways, Boras’ fate this offseason mirrored the sports cliché, “what have you done for me lately.”

“He’s played a gamut and he’s done so well. And you can’t argue with the track record,” Olney said. “But in those two instances, man … that really hurt the player. Matt Chapman turned down about $125 million last spring from the Toronto Blue Jays and he winds up getting a $50 million contract. I mean, there’s no way to sugarcoat that.”

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About Arthur Weinstein

Arthur spends his free time traveling around the U.S. to sporting events, state and national parks, and in search of great restaurants off the beaten path.