The market is cold, and time might not be on Boras and Bregman’s side.
On Saturday, veteran sports writer Mark Powell brought an interesting thought to the table with his latest column as it relates to both Alex Bregman and his agent Scott Boras:
“As always, Scott Boras likes to wait until late in the winter before advising his clients to sign on the dotted line. Under normal circumstances, he'd be wise to do so again. But this market isn't most markets, and the climate is ice cold. The longer Boras waits this time around, the more likely it is that several clients of his – including Alex Bregman – are forced to sign short-term deals and test free agency again in the near future.
“Bregman is 31 years old, and has been linked to all of the Blue Jays, Cubs, Red Sox and Diamondbacks. Surely there are more teams in the mix, but the point remains that the holidays have gone by, and he is no closer to picking his next team.
“This is Bregman's final shot at securing the long-term deal of his dreams. If he signed another short-term contract, he'll reach free agency again in his mid-30's, which will significantly hurt his value no matter what statistics he puts up. Coming off a 3.5 bWAR season in just 114 games, Bregman ought to cash in whenever the offer comes.”
While it feels crazy to question anything about the practices of Boras, who is almost inarguably the most prolific agent in the history of North American sports, Powell may be on to something here.
There have been multiple reports this offseason saying Bregman is in search of the type of contract that would take him to the end of his career, and that he wants that contract to be with the Boston Red Sox.
If that’s not the type of deal that feels plausible to sign in February while Boras uses other teams against each other for leverage, than the 73-year-old is not doing right by his client by thrusting him into this type of bidding war, especially with someone like Bregman who is as championship-driven as anyone in baseball.
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The two-time World Series champion has only missed the postseason one time in his entire 10-year career - his rookie campaign in 2016. When this guy is on your roster, your team is good. And for what it’s worth, his old team in Houston missed the postseason for the first time since Bregman’s year in his first season playing for a different team.
I know last offseason’s free agency for Bregman stretched until February, but that felt like more of the exception than the rule for a guy who is consistently celebrated as the leader of every clubhouse he’s ever been in. If you’re a guy that cares about installing a culture - or keeping the one you built rolling - logic tells you that you want to be a part of the team as early in that foundation-laying process as possible.
Plus, when he waited it out last time, he only ended up with a three-year deal that he and Boras decided to opt out of after only one season. Who is to say that this type of thing doesn’t happen again for Bregman?
The longer they wait, the longer teams are going to have to stare at his games played from last season, or to study the decline he had post quad injury. You marry those two things with his post-age-30 body, and you can see a universe where Bregman is fielding another group of three-to-four year deals.
As someone who has a vested interest in the Red Sox having a successful 2026, I would love for something to get done sooner rather than later.
But as New Year’s Day rapidly approaches, it’s starting to feel less and less like that’s going to happen.
Boras has a very particular way of doing business, and it has helped him become baseball’s top agent. But for this specific instance, I don’t believe it’s in the best interest of Bregman to follow this methodology.
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Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a senior digital content producer for WEEI.com, and a native of Lincoln, RI.