Scott Boras' lofty expectations doom Astros-Alex Bregman negotiations to failure

No one with any brain cells actually thinks that the Houston Astros or any other team is going to be able to sign Alex Bregman for cheap. This is likely Bregman's last chance at a big payday, and with super agent Scott Boras running the negotiations, the likelihood that he would settle for anything less than top dollar is extremely small.

The question, then, becomes what "top dollar" actually means when it comes to Bregman. Outside of Juan Soto, who is going to be one of the highest paid players in baseball history by the end of offseason, Bregman has a strong case as the next best free agent bat available.

Looking at the deals given out to guys like Matt Chapman and Xander Bogaerts, predicting Bregman's next contract to be somewhere in the neighborhood of 7-8 years at around $26-27 million a year felt like a pretty good guess.

However, those who have felt for a while that Bregman was as good as gone since the 2024 season ended got even more ammunition for their skepticism recently. According to a report from Ken Rosenthal at The Athletic, he believes that Bregman is actually hoping for a deal similar to Manny Machado which, if true, probably means he won't be in Houston when the dust settles.

Alex Bregman's contract demands sound wild enough that the Astros should steer clear until he comes back to Earth

Just to be clear, the number of people that think that Bregman will actually get a deal resembling Machado's 11 years and $350 million might actually be just Bregman and Boras. Machado's deal with the Padres was considered at the time to be an outlier, and asking teams to ignore Bregman's power decline and the fact that he is 30 years old seems a huge stretch, to say the least.

However, that Bregman's camp seems to think that such a deal should be on the table is a reminder of the pitfalls of negotiating with Boras. He is in constant pursuit of the next massive, market-setting deal, and while he shouldn't be making the contract comparison with Machado, it's exactly the type of thing Boras would do. While one can hope that Bregman would see reason and look at the market as a whole before digging in on waiting for a specific and lofty number, we saw what happened to prominent Boras clients just last offseason.

At the end of the day, Houston can't afford to wait around while Boras plays his games and Bregman tries to squeeze every dime he can. If the report is inaccurate or if Bregman's demands come down, then the Astros should absolutely be involved, as they have shown they want to be. However, the front office needs to pivot to other alternatives if it looks like Bregman/Boras are going to hold out to the bitter end.

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