Manny Machado Signs Mega-Deal Extension: How is Alex Bregman's Houston Future Impacted?

What Manny Machado's deal means for Alex Bregman

According to Jeff Passan, Manny Machado, one of the best third-basemen in the MLB, just agreed to an 11-year, $350 million extension with the San Diego Padres. This is the fourth-biggest contract ever given out. The deal will carry Machado through his age-40 season.

Last week reports emerged that Machado would opt-out after the 2023 season and was seeking $400 million in free agency. Though that amount wasn't reached, Machado becomes the latest in a long line of players signing decade-long extensions with remarkably high AAVs.

Where does this leave the Astros? Until now, though the tide appears to be turning with Dana Brown in charge, the Astros have avoided long-term extensions like the plague. Brown has made it very clear that Houston will be retaining their homegrown talent moving forward, and has specifically named Jose Altuve and Alex Bregman as players he hopes to retain, saying each should retire in Houston.

Altuve was very transparent, saying Brown's comments were appealing, and that Altuve too, hopes that he retires here. The Astros other key free agent in 2024 was a little more guarded. Though he made clear he loves the city of Houston, the fans and his teammates, Bregman admitted that free agency intrigues him and "we'll see what happens."

If Houston doesn't extend Bregman this off-season, they may very well lose him next off-season when the Padres, Mets, Dodgers or some other mega-spender gets Scott Boras on the phone and offers Bregman a 10-year deal.

Brown and the Astros need to strike now, especially if the rumors of Machado seeking $400 million were true and the Padres inked him for less than his asking price.

So what might it cost to keep Bregman in Houston? It's safe to say he will blow past the five-year, $100 million extension he signed in 2019. A safe starting point would be doubling his salary, which would blow past the richest contract Houston has given out (Altuve's five-year, $151 million extension in 2018).

To gauge Bregman's future contract, whether in Houston or elsewhere, we have to look at those of other third basemen. Rafael Devers, Manny Machado, Nolan Arenado and Anthony Rendon all earn more than $30 million a year. Other superstars like Austin Riley and Jose Ramirez barely top $20 million. Though Bregman is a far better player, a contract to keep an eye on is Josh Donaldson, who has a $23 million AAV. Bregman likely would land between $25 and 28 million, more than MVP candidates in Riley and Ramirez, but less than others in Machado and Devers.

Houston could afford to overpay Bregman due to the steep discounts they got on Yordan Alvarez and Cristian Javier, but they also have Kyle Tucker, Framber Valdez and others to pay. Bregman's 2019 extension will carry him through his age 30 season. We've seen a multitude of big names get the bag at 30.

If Houston can sign Bregman this offseason, they avoid the murky waters of unrestricted free agency and ensure they lock him up for the duration of his prime without having to overpay for his age 40 and 41 seasons. Seven years and somewhere between $175 million and $196 million ($25-28 million AAV) could be enough to keep Bregman in Houston for the remainder of his career. If that's the case, the title window remains wide open.