Whether it's because of his cringy puns or the fact that his players seem to take forever to sign, MLB fans almost universally dislike Scott Boras. Justified or not, what cannot be disputed is that Boras is one of, if not the best, sports agent in history.
Alex Bregman signing a five-year, $175 million deal with the Chicago Cubs during the Chicago Bears' thrilling comeback win on Saturday night is further proof of that. Not only did Boras get Tom Ricketts to spend the money he, for whatever reason, loathes to spend, but he got his client more money than most anticipated.
Scott Boras' risk paid off with Alex Bregman contract
Boy, does this deal make Boras look good. Bregman's contract will pay him a little less than $35 million annually, as there are deferrals involved, but even with the deferred money, Bregman will be one of the highest-paid third basemen in the game through his age 36 season, which is exactly what Boras wanted.
As if that wasn't good enough, with his new contract finalized, Bregman will earn a total of $215 million over his first six post-arbitration years, averaging nearly $36 million annually. Boras took a risk with Bregman last winter, having him settle on a three-year, $120 million deal with opt-outs after failing to secure a long-term deal for his client. This offseason's deal more than makes up for that.
MLB fans don't love his methods, but more often than not, they work.
Alex Bregman deal is latest victory for Scott Boras
It was risky having Bregman settle for a short-term, high-AAV deal, knowing that if he struggled after signing it, he'd never cash in the way he did on this long-term pact with the Cubs. This method worked with Bregman, and he's far from the only one.
Last offseason, Pete Alonso settled for a similar short-term, high-AAV deal as Bregman. He opted out of the contract after a strong 2025 campaign and wound up inking a five-year, $155 million deal with the Baltimore Orioles. In previous offseasons, guys like Blake Snell and Matt Chapman are other examples of players who signed short-term high-AAV prove-it deals and then eventually signed long-term contracts.
It takes a while, it isn't always pretty, and as Jordan Montgomery would admit, it isn't foolproof, but more often than not, Boras gets the job done. He's even done so with other marquee free agents of this year's class.
Alex Bregman is far from only 2025 offseason Boras client to sign huge deal
Alonso getting a big deal might not have been shocking, but who expected him to get more money than the reigning NL MVP runner-up, Kyle Schwarber? Boras got him that. Dylan Cease has all the potential in the world, but he's had an ERA above 4.50 in two of the last three seasons and had a mostly rough 2025 campaign. Despite that, Boras still got him a deal worth over $200 million from the defending AL Champion Toronto Blue Jays.
Boras even did well with his international free agents. Tatsuya Imai might not have gotten the long-term deal some expected, but he got a short-term deal with opt-outs and locked in a very respectable $18 million AAV. Kazuma Okamoto didn't get a nine-figure deal either, but he got a fairly hefty four-year deal from the Blue Jays before taking a single swing in the big leagues.
I say this before Cody Bellinger has signed, and there is a chance Boras will screw up his free agency, but as of now, he's crushed every deal with every one of his big-name clients in this offseason's free agency class. Again, you might not like how he gets the deals or you might be envious of his success, but there's no denying that Boras is still at the top of his game.
Whether it's a player coming off a good year, a down year, or something in between, Boras finds a way to get his client paid. There's a reason players continue to sign with him in droves, and Bregman's deal is just the latest of many Boras wins.
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