With the Red Sox (81-66) entering their biggest series of the season this weekend against the Yankees (80-65) at Fenway Park, Boston fans will have a close eye on how things shake out on Thursday at Yankee Stadium.

Coming off their disappointing 5-4 loss in Sacramento, Boston sits a percentage point behind New York in the wild card standings. And if the Yankees can avoid a sweep at the hands of the Tigers on Thursday (84-62), they’ll have a half-game lead over their AL East rival to start the three-game series.

As I wrote about on Monday, the Red Sox season down the stretch is a bit of a gauntlet, with series on tap against the aforementioned Yankees, Tigers and Blue Jays (83-62), along with a tough three-game set with a scrappy Rays (72-73) team that’s never an easy out.

Add in another three-game series against an A’s team Boston just lost to on Wednesday, and it’s a 15-game stretch where the Red Sox will need to be playing some of their best baseball of the season to secure their first postseason berth since 2021.

But looming over all of this is a report from ESPN’s Jeff Passan last week, saying All-Star third baseman Alex Bregman will exercise his ability to opt out of his contract after the season, once again making the 31-year-old a free agent.

This February, Bregman agreed to a three-year, $120 million deal to join Boston, giving him an average annual salary of $40 million a year. It was and is a lot of money for a player his age, but Bregman’s resume and numbers were that of a player who was in line for one of these late-career overpays you see all the time in baseball.

But instead of signing the decade-plus deal that has fans shaking their head by year four, Bregman and his agent Scott Boras opted for short term with larger coin, while also building in an ability for Bregman to opt out of his deal after each of the three years he was signed up for in Boston.

It was a bet on himself. And so far, so good.

Despite a slump of late, Bregman is batting .279 with an OPS of .836. Even after missing a big chunk of the season with a quad strain in late May, he’s racked up 16 homers and 57 RBI. On top of his success at the dish, he’s continued to play Gold Glove defense at third base.

So what say you, Red Sox team president Sam Kennedy?

He was asked about Passan’s report on Bregman on Thursday’s edition of The Greg Hill Show on WEEI:

“You know, it's interesting. We were all surprised by that report, given we just haven't had discussions with Alex about anything other than the goal at hand right now with what's in front of us these next 15 games. So that'll all take care of itself.

“He wants to be here. We want him to be here. And I'll leave it at that. But he's such an important part of this season and what we're doing. And all the focus right now is on these next 15 games, and fingers-toes crossed, October baseball.”

Nothing to see here, folks! Kennedy? Not worried at all!

All joking aside - if the Red Sox go on a deep run, I can’t imagine Bregman would want to play baseball anywhere else. Fenway Park is a special place in October. He’s only ever experienced that as a member of the opposition. To have a chance at being in the home dugout for those crisp autumn nights, I think it will have real sway over where he wants to play in 2026-and-beyond.

That is, of course, if he plays well.

And, of course, if this team is able to make a playoff push.

And, maybe most of all, if Boras isn’t able to get Bregman some sort of mega-deal he won’t be able to turn down.

Stay tuned.

Tom Carroll is a contributor for Roundtable, with boots-on-the-ground coverage of all things Boston sports. He's a digital content producer for WEEI.com, and a native of Lincoln, RI.