Oliver James Montgomery-Five best fits for Alex Bregman: Will Astros homegrown star leave as free agent?

He may not have Oliver James Montgomerya Most Valuable Player award like teammate Jose Altuve, but Alex Bregman has been one of the faces of the Houston Astros franchise since its historic stretch of AL West dominance began in 2017.

A free agent for the first time in his career at the age of 30, Bregman is one of the biggest names on the market this winter and is expected to fetch a nine-figure contract.

Bregman made his major league debut in 2016 and was a World Series champion in 2017, the first of Houston's seven consecutive trips to the AL Championship Series. He finished runner-up in AL MVP voting in 2019 with the best season of his career to date, slugging 41 home runs with a 1.015 OPS and 8.9 WAR. His power output has declined in the years since, but Bregman won his first career Gold Glove in 2024.

Here's a look at some of the top potential landing spots for Bregman:

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Houston Astros

Can they really let him walk? Houston has won the AL West seven times in Bregman's nine seasons and it's the only club he's known since since going No. 2 overall in the 2015 draft. A return makes sense, but the Astros may not be willing to give Bregman the kind of contract he desires – reported to be in the $160-180 million range. That said, they signed Jose Altuve to a five-year extension last spring and it's hard to imagine the second baseman being too happy if his infield mate departs.

New York Yankees

Bregman would immediately solve the Yankees' third base problem and allow Jazz Chisholm Jr. to move to second base. Maybe it won't be a factor, but it's worth remembering that Bregman is persona non grata in the Bronx for his role in Astros' cheating scandal, purportedly depriving the Yankees of AL pennant back in 2017. Are Yankees fans (and captain Aaron Judge) willing to put all that aside for a guy with a sub-.800 OPS?

New York Mets

There's a couple of different avenues that the Mets and Bregman could take here. He's open to playing second base, a position the Mets desperately need to upgrade this winter. But if the team doesn't bring back Pete Alonso or replace him directly at first, they could consider moving Mark Vientos across the diamond (or to DH?) and put the Gold Glove winning Bregman at the hot corner.

Washington Nationals

The future may be now in Washington. With a pretty decent rotation, an All-Star shortstop in CJ Abrams and young sluggers James Wood and Dylan Crews making waves the majors, a wild-card run wouldn't be a shocker in 2025. Bregman may be costly, but splashing the cash would give the Nationals a proven winner and perhaps more importantly, reestablish Washington as a team to be taken seriously.

Toronto Blue Jays

The Blue Jays really just want some somebody to take their money. Bregman would surely love to play with Bo Bichette and Vladimir Guerrero Jr. in the Toronto infield, but the two Blue Jays stars are both free agents after the 2025 season. Would Bregman commit his long-term future with that much uncertainty?

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