Scott Boras took over the MLB GM Meetings, but by now rival executives can see right through his schtick. The super-agent's wordplay will only get him so far, and while his clients are expected to sign big contracts this winter, he shouldn't get too cocky.
The likes of Alex Bregman, Pete Alonso and Cody Bellinger have been deemed Boras's 'Big 3' this offseason. While they have a combined estimated annual value of around $88 million, give or take, per Spotrac, not every star gets what they want on the free-agent market. Boras always believes it's worth the risk, and that mentality could come back to haunt him in a few weeks.
For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.
Alex Bregman: History can haunt him
In the case of Alex Bregman, he should have plenty of free-agent suitors on paper. The Red Sox, for one, would love to keep him despite the emergence of Marcelo Mayer, who may one day take his position. Bregman played in just 114 games, but had a 3.5 WAR and .821 OPS. It was one of his best seasons in years, and Boston would bank on their 31-year-old star repeating that success in 2026 and beyond.
What could cost Bregman – and thus Boras – millions are some of the teams likely to rival the Red Sox for his services. It's no secret that the Red Sox are favorites to sign the third baseman. What Boras would prefer is to drive up the price with offers from some of their rivals, like the Toronto Blue Jays and Detroit Tigers. The only problem with that strategy is that the Jays and Tigers are unlikely to make the same mistake twice.
Detroit, for one, gave Bregman a better offer than the Red Sox last winter. Bregman wanted six years, and Detroit was willing, in part because the Tigers were desperate for a third baseman. Bregman sent them packing anyway, signing with a Red Sox team he thought had a better chance at winning a World Series. And now he expects the Tigers to circle back? That's not how this works.
Pete Alonso: Battling with Bregman in Boston
As ESPN's Jeff Passan notes, the Red Sox would be interested in Pete Alonso if they lost out on Bregman to free agency. Heck, they might be interested in Alonso either way, but that'll come with a caveat. As much as Red Sox ownership claims they'll spend in free agency, we must always take such statements with a grain of salt.
I find it hard to believe the Red Sox would be willing to add Alonso's expected $28 million AAV on top of the long-term deal they'd have to give Bregman. That's just not smart business for two players over 30 years old. And unfortunately for both players, the longer they debate playing together, the faster their market could move on without them.
Add in that Alonso is willing to move to DH – a position that would make sense for Bregman, eventually, on the long-term deal he desires – and I see a conflict of interest. Boras loves to make all his clients happy, but as we've seen the last few years, that's easier said than done. About that...
Cody Bellinger: Father time comes for us all
While the H2 might suggest otherwise, Bellinger is actually the youngest of Boras' top-3 free agents this winter. At just 30 years old, Bellinger can play anywhere in the outfield and first base. He's also coming off a productive offensive season, where he had an .813 OPS and 29 home runs for the Yankees. New York would like to keep Bellinger around, but at what cost? We'll get to that.
Bellinger was traded to the Yankees just last offseason, but opted out of his contract with the expectation he can make more than the $25 million he was scheduled to receive next season on a long-term deal. He's likely right about that, but Boras would be wise to act quickly before opposing teams do too much digging on Belli.
Bellinger played plenty of center field for the Yankees last season. However, now that he's on the wrong side of 30 years old he projects better as a corner outfielder or first baseman. Those positions, while still valuable, don't offer the same price tag long term for contenders who build through the middle of the diamond. Catcher, starting pitcher, shortstop and center field are arguably the most important positions in the sport.
Boras will try to sell Bellinger as someone who can spend much of his time at one of those positions, but as he ages he will eventually slow down to the point he can't be relied upon defensively up the middle. That is something every interested team must think about before offering Bellinger a long-term contract that'll pay him well into his mid-30's. Baseball is a business, after all.