Yankees Now Predicted to Go In on Top Free Agent After Big Bucks Toronto Deal

With now just 19 days to go until MLB teams open spring training for the 2025 season, the big names in free agency are slowly but surely starting to rake in the big bucks, falling off the board as the pressure of the oncoming season pushes both players and teams to strike deals.

The latest came on Monday morning when former Baltimore Orioles free agent outfielder Anthony Santander — who blasted 44 home runs in 2024, second in the American League behind Aaron Judge — agreed to terms with the Toronto Blue Jays. According to an ESPN report, Santander will sign a deal for five years in Toronto at price tag “worth more than $90 million.”

Jon Heyman of the New York Post reported the full value of Santander’s contract with the Blue Jays to be $92.5 million.

Santander had earlier been reported to be looking for a contract that would pay him at least $100 million, but nonetheless a deal with an average annual value of more than $18 million has got to be impressive for a hitter who was signed by the Cleveland Indians (now called Guardians) out of Venezuela in 2011, could not crack their major league roster and was left unprotected in the Rule 5 draft in 2016.

Blue Jays Now Pushing Top Luxury Tax Cutoff

The Orioles picked him up and Santander developed quickly. Now, the switch hitting slugger is reaping the financial benefits of that long wait for MLB success. But Santander’s jackpot could now act as a handcuff on the Blue Jays, narrowing the field of teams likely to acquire the other top remaining free agent hitter still on the market, former Houston Astros third baseman Alex Bregman. It could also bring down Bregman’s price as his market narrows, meaning that the New York Yankees who have been reluctant to part with the $200 million the nine-year veteran is reportedly seeking.

Toronto was reported to be in on the competition for Bregman, but with the signing of Santander, the Blue Jays’ payroll will now exceed the $261 million set as the second threshold for the MLB Competitive Balance Tax (CBT), also known as the “luxury tax,” meaning that the team will incur additional financial penalties for the privilege of signing him.

They will need to pay a 30 percent surcharge on payroll expenses over the first CBT threshold of $241 million, and now another 12 percent on expenditures over $261 million. According to Ben Nicholson-Smith of Canada’s TV network SportsNet, the Blue Jays payroll after inking Santander sits at $263 million. That means in addition to the at least $6 million in “tax” they must pay for exceeding the first threshold, they just added another $240,000 for signing Santander.

Yankees Bregman Deal Now Possible Under These Conditions

To sign Bregman would mean pushing past the third CBT threshold, adding even more tax payments.

The Yankees current 2025 payroll is slightly over $273 million. To avoid topping the third threshold of $281 million they would need to bring in Bregman for a 2025 payroll sum of less than $8 million. That would likely involve giving the former Astro a contract with deferred payments.

“The Yankees were never going to engage with Bregman on a long-term, Astros-topping deal, but as he flaps in the breeze, the door to a union might open just a crack if he begins to consider short-term deals with opt-outs attached,” according to the Yankees blog Yankees Go Yard.

That means for New York, signing Bregman would probably be contingent on a trade that unloads at least a portion of Marcus Stroman’s $18 million salary.

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