The clock may be ticking on Scott Boras’ MLB reign

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Playoff hero Jordan Montgomery fired Boras after being one of several big-name free agents to sign late for a much lower contract than expected.

For decades now, Scott Boras has been synonymous with the MLB offseason. He changed the landscape of player salaries in such a dramatic way and over such a long period of time that it would not surprise anyone to see a Boras plaque in the National Baseball Hall of Fame one day, à la Marvin Miller. The sports industry writ large has become a massively successful business, and with owners’ profits soaring, Boras and his team did everything they possibly could to get the players their fair share as the actual product on the field.

Everyone knew that Alex Rodriguez was going to get a lot of money in free agency when the superstar shortstop hit the market at age 25. No one could have possibly foreseen the 10-year, $252 million deal he signed with the Texas Rangers. Boras was absolutely essential to making that happen, convincing then-owner Tom Hicks that A-Rod was the future, that Hicks could not let this opportunity fly by, and that he had to put pen to paper.

This was the not-so-subtle secret to Boras’ smashing success: he knew how to talk to the ultimate decision-makers and get them to commit their money to players. Close relationships with late owners Mike Ilitch of the Detroit Tigers and Ted Lerner of the Washington Nationals led to huge deals for the likes of Prince Fielder, Max Scherzer, and Stephen Strasburg. To be clear, Boras knew how to do all the other aspects of the job, and clients across the board — superstars or not — were satisfied with him and felt like he was getting the maximum possible contract.

Now, though, Boras is licking his wounds after enduring his most arduous offseason in recent memory. He had four of the biggest names on the free agent market in two-time Cy Young Award winner Blake Snell, former NL MVP Cody Bellinger, 2023 World Series champion co-ace Jordan Montgomery, and defensive wizard Matt Chapman.

The results of the winter were … not what the players intended.

Contract predictions from FanGraphs’ Ben Clemens.

The worst part of all this was that it was a slow, protracted crawl to the finish line on these contracts. Bellinger and Chapman broke camp with their 2024 teams, but Snell, Montgomery, and fellow client J.D. Martinez had to wait so long to sign that they were inactive on Opening Day. In years past, Boras had found success by waiting out the market, daring to creep into MLB spring training exhibition play. For example, it worked out well for Bryce Harper, who didn’t sign his 13-year, $330 million deal with the Philadelphia Phillies until March 2, 2019.

None of these players, however, had Harper’s upper-echelon pedigree. They all had their own flaws that made teams hesitant to meet Boras’ high demands. Bellinger was one of the worst players in baseball across 239 games with the Los Angeles Dodgers from 2021-22, and some underlying metrics are skeptical about him repeating his recent resurgence. Snell has a pair of Cy Youngs on his shelf, but he also has an earned reputation as a strike-zone nibbler and even led the majors in walks last year with 99. Chapman fell off a cliff after a red-hot April in ‘23 and hit just .205/.298/.361 for the rest of the year. And Montgomery is generally perceived as a high-floor, solid starter rather than the sub-3.00 ERA stud he was after Texas acquired him for their run to the World Series.

Bellinger re-signed with the Chicago Cubs on February 27th for a three-year deal that is tantamount to a second consecutive “prove-it” contract, with player options after both 2024 and 2025 in case he wants to try the free agent market yet again. Chapman took a similar deal from the San Francisco Giants on March 3rd. After turning down the New York Yankees’ $150-million offer in January, Snell settled for $88 million less from those same Giants on March 18th. And just before the 2024 season began, news broke that Montgomery would accept a mere one-year deal from Arizona with a vesting player option for 2025.

Montgomery technically waited until the day after Opening Day to sign his deal so that he didn’t have a qualifying offer attached to him for the 2024-25 offseason, so he’s hopeful of entering the market again. He will not be doing another round of this with Boras though, as he has reportedly fired the longtime agent.

Boras has been able to get away with signing these “B+” and “B”-caliber free agents in the past through his various machinations. In a perfect world, teams wouldn’t hesitate to pay top dollar for top talent, but it’s the agent’s job to properly read the market climate. The business of baseball in 2024 mostly operates through specific channels, and some doors aren’t as open as they once were. Cubs chairman Tom Ricketts said it himself back in mid-February when the team was still negotiating with Boras over Bellinger:

It’s taken a long time, and some ball clubs were even signing suspect Boras clients to big contracts in the previous offseason.

The tide may have finally turned, though. If more and more teams are throwing up roadblocks to ownership and limiting Boras to only negotiating with presidents of baseball operations and general managers, then that could be trouble. That’s to say nothing of Boras’ own tenuous reputation among the rank-and-file of the MLB Players Association, who have grumbled about leadership being too close to Boras. There is a sizeable number of Boras clients out there who will defend him, but anyone not tied to him will raise eyebrows at what happened this past winter.

It’s important to note that Boras has not fully lost his touch. KBO standout Jung Hoo Lee signed with San Francisco for six years and $113 million, far more than FanGraphs forecast at four years and $60 million. That was a notable win for Boras Corp., as was the Houston Astros extending franchise icon Jose Altuve for five years and $125 million, up through the year he turns 39 (though owner Jim Crane’s sentiments toward Altuve undoubtedly played a key role there).

Boras has a couple huge free agents coming up for the 2024-25 offseason in Juan Soto and Alex Bregman. Soto is like Harper — a young, slam-dunk superstar who will have no problem commanding a monster deal. He will not be waiting until Opening Day 2025 is breathing down his neck, and he will get paid handsomely. Even if he’s not the 8.9-WAR player he was in 2019, Bregman’s a fierce enough hitter to likely cruise to a nice payday, too.

But for all the Boras clients below this “A+” and “A” class? They might have to tread carefully if he’s reluctant to budge on his tactics.