Scott Boras has built a decades-long reputation as arguably the most intense, principled negotiator in MLB. Folks don't always love those principles, but Boras sticks to his guns and gets his clients paid, more often than not.
His modus operandi is fairly simple: Never, ever take the extension (with a few exceptions, depending on the player and the team). Boras represents some of the biggest names in MLB and he values the open market above all else. He wants to drum up a bidding war and take the best offer available, loyalty be damned. When your Boras-represented star hits free agency, the odds of him re-signing are dramatically lower than they might be with another agent. Heck, with another agent, it's easier to keep your star from even reaching free agency.
Boras was the mastermind behind Juan Soto's historic 15-year, $765 million contract with the New York Mets last winter. And Bryce Harper's current deal in Philadelphia. And countless other noteworthy salaries around the league, including multiple 2026 free agency headliners.
Another core Boras tenet: If he can't get the long-term money he wants, don't expect his clients to settle. Instead, they will take a short-term, front-loaded contract with opt-outs, allowing them to test the waters again as soon as possible. See for example: Pete Alonso, Cody Bellinger and Alex Bregman. All of them were free agents last winter and are back on the market this offseason.
If not for Boras, it's fair to wonder how many of these guys wouldn't even consider leaving their current setup.
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OF Cody Bellinger, New York Yankees
Cody Bellinger was basically salary-dumped by the Chicago Cubs to create space for Kyle Tucker, a move that has aged in complicated fashion as Tucker's free agency looms large. One can't help but wonder if Chicago might have better odds of re-signing Bellinger, with a six-year, $182.7 million market value, per Spotrac. That feels far more palatable for a notoriously risk-averse Jed Hoyer compared to Tucker's whopping 10-year, $401.8 million market value.
But that's all besides the point. Bellinger spent this past season with the New York Yankees, where he turned back the clock and put together one of his best individual campaigns since leaving the Dodgers. Bellinger hit .272 with an .813 OPS and 125 OPS+, notching 29 home runs, 98 RBI and 13 stolen bases, all while supplying plus defense in left field.
Bellinger's injury history and age (30) complicate these upcoming negotiations, but he's such a strong fit on a Yankees team that can't really afford to lose his production in the outfield right now. New York wields significant spending power and there's not a more appealing market east of L.A., but still, the Yankees will face competitive bids from clubs like the Mets, Phillies and maybe even the Dodgers. The Yankees lost the Soto bidding war by a fraction, so don't expect Bellinger to weigh any loyalty or market appeal when making his decision under Boras' guidance.
3B Alex Bregman, Boston Red Sox
Alex Bregman took a balloon deal, three years and $120 million, with significant deferred money, to join the Boston Red Sox last offseason. He fielded a longer-term offer from the Detroit Tigers, but the annual value was not up to snuff and thus Bregman decided to keep his options open. Now, after a productive campaign in Beantown, the former World Series champ is back on the market.
The best outcome for all parties is a reunion. Bregman is beloved in Boston and he clearly enjoyed his time at Fenway. The Red Sox have a ton of young infield talent coming up through the farm system, but this team is hoping to compete next season and there still isn't a third baseman close to Bregman's caliber on the roster. Boston can bring Bregman back as a mentor for Marcelo Mayer, Kristian Campbell and others — not to mention as a lynchpin in the lineup next to Roman Anthony.
And yet, money will win the day here. Boston was unwilling to shell out a six- or seven-year contract last winter and it's unclear if Bregman has done enough to change their minds, especially with all that in-house talent waiting in the wings. Bregman finished the season with solid numbers — .273 average and .821 OPS (128 OPS+), knocking 18 home runs in 433 at-bats — but his production was uneven overall. Bregman was electric for a few months to start the campaign, but he finished ice-cold as injuries took their toll and disrupted his rhyhtm. He's another year older now, and Boston could be convinced to pursue other options if Bregman is too stingy with his demands. Time will tell.
1B Pete Alonso, New York Mets
Pete Alonso spent months toiling in the free-agent pool last offseason before finally agreeing to a short-term contract with opt-outs in Queens. He put on a show for the Mets, as expected, hitting .272 (a career high) with an .871 OPS and 144 OPS+. Alonso tallied 38 home runs and 126 RBI, building upon his résumé as one of the great sluggers of his generation.
The Polar Bear, as those in New York affectionately refer to him, is basically a Mets legend already. He is adored by that fanbase and after seven great seasons, it's hard to imagine the five-time All-Star just picking up and leaving. He has been connected to teams like the Yankees (ew), Red Sox and even the Phillies (I'm open to it, but Mets fans certainly are not).
One would expect New York to covet Alonso after such a disappointing season. The calling card for this Mets team is their ability to hammer a baseball and Alonso serves as excellent protection for the fellow Boras client and $765 million man in Soto. But David Stearns tends to fade players in the Alonso mold and if he attacks free agency looking for a huge, long-term commitment, New York probably lets him walk.
LHP Tarik Skubal, Detroit Tigers
Tarik Skubal is entering the final year of his contract with the Tigers. Spotrac pegs his free agent market value next winter at eight years and roughly $300 million. Frankly, there's a chance Skubal could get upwards of $100 million more than that given his status as the best pitcher in the American League. Detroit is an excellent organization top to bottom, but the odds of Scott Harris and ownership spending on the level necessary to extend Skubal are slim to none.
This sets up the potential continuation of an increasingly frustrating trend for Tigers fans. Justin Verlander, Max Scherzer — generationally gifted aces just keep falling through the cracks. Detroit can develop talent internally as well as any organization in MLB, but their inability to keep those players long term is a real limiting factor.
Skubal has nothing but love for Detroit, and we know the Tigers want to keep him. It's fair to expect Harris and the front office to extend a little bit beyond their comfort zone in an effort re-sign the fireballing southpaw. At the end of the day, though, the Tigers can't (and won't) win a bidding war, which is precisely what Boras envisions for his client a year from now. Skubal is going to test the waters, run up the price and take the best offer sheet on the table. Odds are it's coming from New York, Los Angeles or Boston — not Motor City.