The MLB postseason rages on, but the season of Scott Boras is already underway. Sure, free agency doesn't technically begin until five days after the conclusion of the World Series. But with 26 front offices already making plans for 2026, the foundation is already being laid — and this winter, like pretty much every winter, Boras will be the man of the hour.
There might not be another Juan Soto on the market, and this winter is unique in that the biggest fish — Kyle Tucker — is not a Boras client. Instead, Boras will have to try and find his big paydays with a trio bats: former New York Mets first baseman Pete Alonso, former Boston Red Sox third baseman Alex Bregman and former New York Yankees outfielder Cody Bellinger. (Bregman hasn't officially opted out of his contract yet, but come on: He's a Boras client.)
The Soto sweepstakes showed that Boras can still very much deliver the goods in a bidding war. Then again, generational hitters who just turned 26 years old don't grow on trees. Each of Boras' top clients this offseason come with at least some cause for hesitation, hesitation that Boras will have to work around if he wants to land them the sort of megadeals that have become his hallmark. How realistic is that this time around? Let's break it down, player by player.
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How much can Scott Boras make some of MLB's biggest stars this winter? Not as much as he hopes
Pete Alonso
On the one hand, Alonso is going to be in the lineup every single day and hit around 40 homers per season, like clockwork. He has the sort of pop that will play in any ballpark, and he's coming off a year in which he cut his strikeout rate while hitting the ball as hard as he ever has. Just about every team in baseball would kill to have a bat like the Polar Bear's in the middle of their lineup.
On the other hand ... there's everything else. Alonso is about to turn 31, and his is not a skill set (or a body type) that you'd expect to age particularly well. He's also one of the worst defensive first basemen in the game, and while the universal DH would in theory help mitigate that concern, Alonso has been vocal in the past about wanting to continue to play the field. He and Boras are reportedly set to ask for the moon on the open market, and it's not hard to imagine a world in which he lives up to that lofty price tag for a year or two before becoming a real liability.
Realistically, not even Boras has enough juice to convince some poor team to agree to a seven-year deal at any significant amount of money; the prospect of a 35-year-old Alonso is enough to give execs pause, much less paying him until he's 37 or 38. Which leaves he and Boras one of two options: Continue taking short-term deals at higher AAVs, or sacrifice some annual salary in exchange for more long-term security.
In the end, I think Boras finds a middle ground. Neither he nor Alonso want to keep going year-to-year like last winter, but I also just cannot see any team meeting the current price. Something in the four- or five-year range at $20-25 million per seems like the best they're going to be able to do, unless Boras pulls his greatest magic act yet.
Alex Bregman
Bregman is nine months older than Alonso, and he doesn't have the same sort of impact as a hitter. Still, Boras is likely to find a hotter market here for a number of reasons: Bregman is still one of the better third basemen in the game, for starters, and his excellent plate approach and contact skills should help him age a bit more gracefully.
It's not all that hard to imagine Bregman remaining at least above-average with both the bat and the glove for several more years to come, and that value — plus his reputation as a clubhouse leader — should have teams a bit more willing to break the bank to bring him in. Heck, just last winter the Detroit Tigers reportedly had a six-year, $170 million deal on the table, and while Bregman is a year older now, his outlook feels more or less the same.
Of course, we know that free agency is not strictly speaking a rational market, and there's another bit of leverage that Boras will be able to play here — one that he uses as well as any agent in any sport. The Boston Red Sox simply cannot afford to let Bregman walk this winter, not after running Rafael Devers out of town in what amounted to an infield power struggle. Sure, you'd hope that Trevor Story opts into his contract and that former top prospect Marcelo Mayer locks down second base next season, but Boston's infield remains in flux — especially with Triston Casas' status up in the air as he recovers from major knee surgery.
This is not a negotiation the Red Sox can afford to lose; if Bregman leaves, they're going to be left scrambling, hoping that Mayer can shift to third and that Kristian Campbell is more ready to be a big-leaguer starter than he looked as a rookie. For a team whose championship window is right now, that's a non-starter. All of which is to say: Expect Boras to have little trouble landing Bregman the five- or six-year deal he seeks this time around, with $30 million per as the benchmark.
Cody Bellinger
If you just go by the top-line numbers this year, you'd think that Bellinger's free agency would be a pretty open-and-shut case. Former MVPs who go 29/13 with a 125 OPS+ while playing elite defense across multiple outfield spots don't exactly grow on trees, and Bellinger just turned 30 in July.
Of course, we all know why it's a bit more complicated than that. For starters, Bellinger is just three years removed from a truly abysmal end to his tenure with the Los Angeles Dodgers. And then there's the fact that his batted-ball profile is pretty underwhelming for a player of his stature. Bellinger has made it work by making a ton of contact, hardly ever striking out and pulling a ton of fly balls, and at a certain point overperforming your underlying metrics is no longer a fluke. Still, it's a unique profile, and one that requires more of a leap of faith than someone who consistently hits the ball hard.
All of those qualifiers aside, though, this feels like a case in which Boras will work his magic. Bellinger is a name brand, for starters, and the production over the last three years remains very strong. Plus: For the teams who miss out on Tucker, who else is there, much less with the ability to play center field? Trent Grisham? Ramon Laureano? Harrison Bader? Boras will likely wait Tucker out and then pounce on the Cubs or Yankees or Giants or Mets or anyone else that has money to spend and a hole in the outfield, and that sort of environment is one in which he thrives.
In the end, I have a hard time thinking Bellinger doesn't get the sort of deal he's looking for, with a team paying him $25-30 million a year for at least five or six years. The defense is that good, and the conditions are ripe.