Alex Bregman created a nearly decade-long legacy at Daikin Park. From season-defining hits and highlight reel catches to October wins and losses, it’s a venue where he played 601 games. He stepped up to the plate 2,160 times, recording 375 runs, 581 hits, 125 doubles, seven triples, 106 homers, and 357 RBIs with an .849 OPS. But, there’s one thing that the Astros ballpark hasn’t seen. It’s Bregman in another team’s jersey. That will change on Monday night when the Boston Red Sox will start a three-game series against the Houston Astros.

It hasn’t been long since the Red Sox handed the Astros a series sweep back in Boston. Yet, the Astros are leading the American League West with a half-game lead over the Seattle Mariners. But Monday night is about Bregman and his visit to Daikin Park as a visitor more than anything else.

After the Red Sox wrapped their series on Sunday against the Padres with a 6-2 loss at Petco Park, Bregman expressed his excitement to play at Daikin Park against the Astros.

“I think it’s going to be great. It’s going to be cool. In Houston, playing against a really good ballclub and looking forward to going out there, competing with the guys and trying to get some wins,” he said while speaking with NESN. Continuing further, he added, “Two playoff teams getting after it. So I think it’s going to be a really good atmosphere, for sure.”

When asked what he’s looking forward to the most, he replied, “Just seeing the guys, seeing the people who work at the stadium, seeing the fans, and playing baseball.”

It’s not just two playoff teams facing off late in the season—there’s some recent history between them, too. During the last series, Astros pitcher Hector Neris was upset over something Red Sox third base coach Kyle Hudson had said. It led to benches getting cleared as the tensions flared up.

But this time, it’s Bregman’s homecoming. So, as he steps into the box for his first at-bat against former teammate Christian Javier, he will perhaps get a thunderous applause from his Astros fanbase, despite the fact that he’s a Red Sox now. But how long is he planning on staying in Boston?

Why Alex Bregman might not sign a contract extension with the Red Sox?

So, here’s the thing: Alex Bregman signed a three-year, $120 million deal last winter. The contract was inclusive of an opt-out clause after the 2024 and 2025 seasons. And, Bregman is expected to use his opt-out clause after this season. It will allow him to chase a richer and higher bid paired with a long-term contract.

Across 313 player appearances this season, Bregman has been hitting .298/.380/.531 with 14 home runs. If he tests the free agency waters, then he is highly likely to land a desired deal. Time and again, Craig Breslow, the Red Sox’s chief baseball officer, has commended Bregman’s impact on and off the field. Similarly, manager Alex Cora has the same stance for the veteran.

“He’s going to help a lot of people in this organization… All he knows is October, and he’s been successful playing in October. He’s going to make people better, and he’s going to challenge people with his baseball IQ. He’s going to ask questions about pitching, defense, offense, baserunning. It’s refreshing to have a guy like that in the clubhouse,” Cora said back in February.

The club had recently extended rookie sensation Roman Anthony to an eight-year $130 million deal. The Red Sox displayed their willingness for a long-term contract. According to Mark Polishuk of MLB Trade Rumors, Bregman’s team might look for a deal in the vicinity of five years and $165 million in order to reach the $200 million guarantee that Scott Boras targeted back in the 2024-2025 season.

Bregman’s contract situation is quite similar to Matt Chapman’s recent contract path. He also signed a multiyear deal with opt-outs before he finally agreed to a long-term extension. Yet, unlike Chapman, Bregman has not hinted at any plans to sign a contract extension before free agency. It suggests he prefers to test the market.