4 MLB free agents Scott Boras has screwed over the most this winter: Bregman or bust

Don't call it a comeback — not quite yet, anyway. On the heels of one of the most humbling offseasons of his career in 2023, one that saw several key clients push their free agencies all the way into Spring Training in hopes of a long-term contract, Scott Boras entered this winter hell-bent on revenge. And, early on at least, it looked like he got it: Blake Snell signed an objectively strong five-year, $182 million deal with the Los Angeles Dodgers in November, and Juan Soto shattered the baseball record books with a $765 million contract that looks sure to climb north of $800 million thanks to an opt-out after year five. The demise of baseball's premier super-agent, it appeared, had been greatly exaggerated.

... or so we thought. While early returns on Boras this offseason were positive, there's a chance we may have jumped the gun a bit. Any random fan off the street could likely have secured north of $700 million for Soto, while other top names like Corbin Burnes and Sean Manaea took matters into their own hands in routing themselves to the Arizona Diamondbacks and New York Mets, respectively. (And given how scorching hot the pitching market has been this winter, that might not have had a ton to do with Boras.)

And he's been far less successful with his other big-name clients. As Pete Alonso and Alex Bregman continue to twist in the wind, running out of leverage by the day, let's take a look at some players who probably aren't thrilled with their agent right about now.

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4. Tyler O'Neill

O'Neill jumped the outfield market in a big way, agreeing to a three-year, $49.5 million deal with the Baltimore Orioles before the Winter Meetings had even convened. Which, from a certain angle, is understandable: O'Neill's checkered injury history hampered his market a bit despite a big season with the Boston Red Sox in 2024, and righty corner bats don't tend to fare all too well on the open market.

Looking back, though, was this really the right move for him? For starters, we still don't know how the renovated Camden Yards will play; even though the team is finally moving the left-field fence in, it's still unlikely to be as favorable a hitting environment as Fenway was. And rolling the dice on a shorter-term deal with an opt-out after year one was a bit curious, considering O'Neill's injury history and the risk that he might get hurt or underperform and see his market crater. He won't turn 30 until June, and while he has a shorter track record of success than, say, Teoscar Hernandez, it was still surprising to see him take so much less, especially so early in the winter.

3. Cody Bellinger

Hear me out here. No, Bellinger probably wouldn't be able to do any better than the $25 million he's set to earn in 2025, at least from an annual average value perspective. And maybe, with his swing tailor-made to hit at Yankee Stadium, he'll enjoy a monster year that will allow him to opt out next winter and finally cash in.

More likely, though, he'll continue to be a solid but not superlative player, one who will be on the wrong side of 30 next offseason, and that mega-deal will once again fail to materialize. The New York Yankees were clearly desperate after losing out on Soto, an outcome that Boras should have been able to see coming. Why not put the squeeze on Brian Cashman and force him to pay up amid competition for Bellinger's services, while he's still 29 and coming off a solid season? Boras often lets the perfect be the enemy of the good, and it might come back to bite him here.

2. Pete Alonso

Speaking of which: It wasn't Boras who convinced Alonso to turn down the nine-figure extension the Billy Eppler-led Mets offered back in 2023, but it has been Boras who's been advising him during what's turned out to be a disastrous offseason for the Polar Bear. Granted, some of that isn't his fault; the market has never been kind to bat-only first basemen on the wrong side of 30, and teams that should be motivated to land Alonso simply haven't been spending this winter.

But Boras has clearly acted as though he could wait the Mets out and get Alonso back to what is clearly his preferred destination, and that turned out to be a drastic misread of the situation. New York is likely just posturing when it leaks that it's moving on from Alonso, but even if the two do eventually reconcile, it'll likely be for a fraction of what he was offered two years ago. If Boras had acted with a bit more urgency to secure a deal, one that was still good even if not on the level of Prince Fielder, Alonso might not be in this position.

1. Alex Bregman

But no one should have a bigger beef than Bregman, who turned down a healthy offer from the Houston Astros in expectation of a contract nearing the $200 million threshold that has simply never materialized — and was likely never going to. There are plenty of teams interested in Bregman's services, but most of them have already made moves compromising their payroll, and Boras put the two-time All-Star in a bad position by misleading him as to just how motivated those teams would be to pay a 30-something position player at a non-premium position. A cold market bears some responsibility for the fact that he remains unsigned, but in a parallel universe he could be getting ready to report to Spring Training in a few weeks with a nine-figure contract.