Alex Bregman's contract with Red Sox shows Yankees still refuse to game the system

You've heard the news by now: Alex Bregman is a member of the Boston Red Sox. The New York Yankees watched the star slugger sign a three-year, $120 million contract with their rivals on Wednesday night.

Maybe the Yankees didn't want Bregman. Maybe they didn't want him earning the same AAV as Aaron Judge (which is objectively ridiculous). But whether they were aligned on the former Astro or not, there should have been a concerted effort to not have him land within the division, and especially with the Red Sox.

The frustrating part is that the Yankees need a third baseman, as they head toward Opening Day without another important full-time role completely unsolved. The other frustrating part is that the Yankees are watching their direct competition in the Dodgers and Mets go to great spending lengths while Hal Steinbrenner and Brian Cashman work harder and harder to impose financial restrictions to avoid another luxury tax penalty.

Yankees still haven't figured out how to manage luxury tax, go above and beyond

For decades, the Yankees represented the luxury tax penalty. They were the bad guys overspending and getting who they wanted. Now? They sometimes get who they want. More often than not, they lose out on players involved in bidding wars and try to make low-risk, high-reward additions on the trade market. They're not necessarily bad at that, but it's proven to be a strategy that clearly plateaus and keeps them from achieving their ultimate goal.

If the Yankees knew the Red Sox were among the most likely destinations for Bregman, then why wouldn't they have gamed the system with deferrals or signing bonuses to acquire him, fill third base, and steal a target from their rival? They have the ability to do it.

And they might not be able to do it for long! The CBA will expire after the 2026 season, and you know there will be revisions regarding payrolls, taxes, deferrals, signing bonuses, etc. after all the hoopla both the Dodgers and Steve Cohen caused over the last few years.

Boston's deal with Bregman has "significant deferrals" with the present-day value of the deal estimated at $90 million. His CBT hit for 2025 is expected to be ~$30 million. He has opt outs after each season, meaning there's a great likelihood he will depart after 2025 assuming he has another All-Star-caliber season.

Why couldn't have the Yankees maneuvered here? We're just wondering. If the CBT hit was $30 million based on the deferrals, the Yankees could've given him a $20 million signing bonus and counted $10 million toward the CBT this year, which would've still had them under the Cohen Tax threshold.

Maybe we're missing some more complications in the process, but once again, it seems like a relatively straightforward solution from the outside that the Yankees refuse to employ to put their roster over the edge.