Major League Baseball’ s offseason is truly an annual free-for-all, with more than 100 free agents aiming for guaranteed contracts and 30 general managers ready to strike when the right deal comes around.
Yet there’s typically one traffic cop orchestrating much of the mayhem: Agent Scott Boras.
For the past two winters, baseball’s silly season has been marked by a half-dozen of his clients festering on the market into – and in some cases, for most of – spring training.
Yet like a cat with nine lives, the struggling Boras client is a flexible creature, capable of playing their way back into financial good graces. And if anything, we’ve learned that it’s never really over for clients of the uber agent.
With Alex Bregman’s three-year, $120 million agreement with the Boston Red Sox, all six lingering Boras clients have homes – some of them permanent. A look at Scott’s Six and how they ultimately fared, even as some may soon hit the market again:
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Blake Snell: Six years, $214 million
First time around: Signed two-year, $32 million deal with San Francisco Giants, but opted out after getting paid $32 million in 2024.
Second shot: Signed five-year, $182 million deal with Los Angeles Dodgers, with $52 million signing bonus and $66 million deferred.
Outlook: After Snell’s dynamite second half following a soft launch after his delayed spring training, it’s clear teams erred in the 2023-24 offseason when they did not lock down the two-time Cy Young Award winner when they had the chance. While deferrals reduce the present value of his per annum from $36.4 million to about $32 million, it certainly would have been easier for someone simply sign him to a $192 million deal a year ago.
Matt Chapman: Seven years, $169 million
First time around: Signed three-year, $54 million deal with Giants, but opted out after earning $18 million in 2024.
Second shot: Signed six-year, $151 million extension in September 2024, nullifying the final two player options.
Outlook: Snell’s late-spring running mate from a year ago shined in the field and at the plate in San Francisco, and by season’s end was identified as a franchise cornerstone. His adjusted OPS of 125 was his best since 2019, allaying fears that Chapman would be a glove-only value.
Alex Bregman: Three years, $120 million
First time around: Signed three-year, $120 million deal with Boston Red Sox, with opt-outs after the first two seasons.
Outlook: A solid outcome for Bregman, whose dashed hopes for a longer-term deal and cracking the $200 million mark are softened by his $40 million annual haul. It will be fascinating if Bregman opts out after this year, perhaps sacrificing that elite salary (albeit with deferred money) for a longer-term guarantee. Observers almost unanimously agree Bregman will crush Fenway Park’s Green Monster – he has a 1.240 career OPS there – and it’s not hard to imagine a Chapman-esque, longer-term relationshp with Boston as he perhaps take over third base from Rafael Devers in future years.
Cody Bellinger: Three years, $80 million
First time around: Signed three-year, $80 million deal with Chicago Cubs, with two opt-out clauses. Traded to New York Yankees this offseason.
Outlook: Ever since the Dodgers non-tendered Bellinger in November 2022, he’s been in largely the same stratosphere: Good, not great. A solid platform year with the Cubs (.881 OPS, 139 adjusted, though in 130 games) couldn’t convince suitors he’d consistently maintain his four-win production and top the 150-game mark. So he opted in for a second year after his adjusted OPS dropped to 111; after a trade to the Bronx, perhaps depositing balls into Yankee Stadium’s right field porch will unlock an opt-out and further riches this winter.
Pete Alonso: Two years, $54 million
First time around: Signed two-year, $54 million deal with Mets, with opt-out after first season.
Outlook: Nobody here has more at stake this year than the Polar Bear. At 30, he’s not quite a year younger than Bregman yet does not play a premium position, and famously turned down a $158 million extension with the Mets long before hitting the market. Now, he must bang his way into an opt-out – he’d make $24 million in 2025 – to get back into the nine-figure rent district, post-free agency.
Jordan Montgomery: Two years, $47.5 million
First time around: Signed one-year, $25 million deal with Arizona Diamondbacks, with a player option that vested for $22.5 million.
Outlook: The lone Boras Four client to fire his agent after his market experience turned sour, Montgomery’s 2024 campaign was nightmare fuel, signing late like Snell yet not turning around his fortunes and then having his owner publicly rip the contract he gave him. But a bullish 2025 after posting a 6.23 ERA a year ago could go a long way toward the riches the now-Wasserman client expected in the winter of ’23-24 – perhaps after Arizona trades him.
