Alex Bregman hits free agency after nine amazing years with the Houston Astros. He was a key part of each of the seven trips to the ALCS, including both World Series teams. Now, he is open to leaving the team if the right deal comes along. The Athletic's Ken Rosenthal reported Monday that Bregman is looking for a Manny Machado contract this offseason.

“The Athletic’s Tim Britton projects a seven-year, $189 million contract for free-agent third baseman Alex Bregman. I suspect that Bregman and his agent, Scott Boras, are aiming higher — specifically, at a deal closer to the 11-year, $350 million extension Manny Machado signed with the San Diego Padres in February 2023.”

Rosenthal continued, “Preposterous? Maybe, considering that another of Boras’ third base clients, Matt Chapman, recently signed a six-year, $151 million deal. The Machado extension, which prevented him from opting out at the end of ’23, resulted in part from the passion and generosity of the late Padres owner, Peter Seidler. Other teams, including Bregman’s previous club, the Houston Astros, likely view it as an outlier. But the statistical comparison between Machado and Bregman is closer than one might think.”

Rosenthal says that Bregman and Macahado are a similar age, have similar OPS+ numbers, and have similar WAR. Machado had more at-bats because he did not play college ball, but Bregman has an argument.

Alex Bregman working towards a big contract

Houston Astros third base Alex Bregman (2) hits a single against the Detroit Tigers during the second inning of game two of the Wildcard round for the 2024 MLB Playoffs at Minute Maid Park.
Thomas Shea-Imagn Images

Part of the issue for Bregman is that someone has to give him the $350 million contract. Rosenthal mentioned that then-Padres owner Peter Siedler was a major reason for the massive Machado contract. While he is an excellent player, there may not be the market for a $350 million 30-year-old.

The Dodgers have Max Muncy at third, the Yankees are focused on Soto, the Mets have Mark Vientos, and the Phillies probably aren't going over $300 million again while Trea Turner figures it out. That eliminates four of the very few teams who can pay the Machado contract. The Astros should not give Bregman that much money, as they have faith in their development system to bring up a new infielder.

Last winter, Scott Boras's eyes were bigger than his stomach, metaphorically. Blake Snell and Jordan Montgomery held out for a long-term deal but ended up on one-year contracts when those did not come. Bregman cannot let that happen, as he is one bad year away from not getting the projected $172 million let alone $350 million.