The New York Yankees are not signing Alex Bregman. It's just not going to happen. But if they possessed a shred of creativity based on their own preferences, they very well could! So let's live in a partially alternative universe for a moment.
For the 2025 season, the Yankees are very obviously hell bent on remaining below the Cohen Tax threshold, which is $301 million. According to Spotrac, the Yankees are ~$20 million away from that mark.
So, in theory, someone like Bregman, who should command over $20 million per season, isn't attainable, unless the Yankees clear more salary. And even then, the front office definitely wants some breathing room so they can be flexible at the trade deadline and not worry about limiting themselves with certain acquisitions.
But — also in theory — Bregman's reported demands are right up the Yankees' alley. Recent buzz suggests the All-Star slugger is still looking for a six- or seven-year deal, even after all this time. Isn't that an opportunity for the Yankees to do their favorite thing? Whenever they can, the Yankees stretch out contracts for more years so they can limit the CBT tax hit over time.
In this scenario, a seven-year deal for Bregman might seem excessive, but is it? The Yankees gave Max Fried eight years. They gave DJ LeMahieu six years. They gave Aaron Hicks seven years. They took on Giancarlo Stanton's 13-year deal.
Free agent third baseman Alex Bregman still has no interest in a short-term contract and seeks a 6- or 7-year deal.
— Bob Nightengale (@BNightengale) February 6, 2025
Yankees Rumors: Alex Bregman's contract demands should actually appeal to New York
For the sake of this exercise, let's say the Yankees don't want to pay a lot up front for Year 1 of Bregman. Perfect, you have another six years to level it out, and over that span, players like LeMahieu Stanton, Marcus Stroman, Gerrit Cole and Carlos Rodón will be coming off the books. After 2028, only Fried and Aaron Judge are guaranteed to be wearing pinstripes.
If Bregman wants seven years and $175 million, what's the harm in tossing him a signing bonus, making his CBT hit for 2025 around $10 million, and then paying him somewhere between $25-$35 million from 2026-2031? Is it ideal? Not at all. But the Yankees can afford it, and they can drastically improve their rapidly closing window, which is likely only going to last three more years.
Famously, the Yankees do not go after players looking for short-term, high AAV contracts, which a number of teams, such as the Chicago Cubs and Boston Red Sox, have reportedly been looking to complete with Bregman. The Houston Astros reportedly still had a six-year contract on the table for Bregman in recent days. The Detroit Tigers are said to be in the same range, but details have been scarce. The Blue Jays might be there, too.
If the Yankees can go up to seven years and limit the payroll hits from 2025-2028 to maintain financial wiggle room, all parties will be satisfied. And so what if they'll be paying for an aging Bregman, Judge and Fried come the 2030s? At that point, it won't matter. They'll be able to work around $100 million of contractual commitments when that time comes.
The focus is now. Enough of heading into spring training with 1-2 glaring roster holes that eventually become the team's undoing.
