The Philadelphia Phillies’ offseason has been productive, if not transformative. Dave Dombrowski has done his job and made the team better. Jesus Luzardo is possibly the best fifth starter in the National League, while Jordan Romano and Max Kepler figure to settle nicely into their respective roles.

That said, it’s been a while since the Phillies truly broke the bank for a top-shelf free agent. That is the kind of move Dombrowski has made a career out of, aggressively outbidding rivals and going after the very best players on the market. There were fans in Philadelphia who desperately wanted Luis Robert and Garrett Crochet at the 2024 trade deadline. This offseason, folks were pining for Kyle Tucker or even Juan Soto. None of that ever felt especially realistic, though.

Here’s the simple truth of the matter: Philadelphia currently has the second-highest payroll in MLB at $279,332,617. That is… a lot. Even Dombrowski and the notoriously ambitious John Middleton hit their limit eventually. The Phillies were never going to cross the $700 million threshold for Juan Soto or even bid up the price tag on Alex Bregman.

Philadelphia’s present financial restraint should be short-lived, however, as Dombrowski has roughly $75 million coming off the payroll next winter. Some of that will, ideally, be used to re-sign the likes of Kyle Schwarber and JT Realmuto, but the 2026 offseason is Philadelphia’s chance to really toss some dough around in free agency.

Ironically enough, the Phillies’ decision to back off on the aforementioned Bregman could adversely impact those plans.

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The obvious Phillies target next winter would be Kyle Tucker, who barely agreed to contract terms with the Chicago Cubs in his final year of arbitration eligibility. Acquired via trade this offseason, Tucker figures to immediately elevate a mediocre Cubs offense, but… he’s in the final year of his deal, and we know how Jed Hoyer does business.

That said, Chicago has made an effort to placate Tucker and boost morale. They relented on their initial contract stance and paid him fair market value. Then the Cubs traded for Ryan Pressly, another former Astros champ who fulfills an invaluable role in the bullpen.

Next up for Chicago might just be Bregman. The Cubs are quietly picking up steam in the Bregman hunt, with a potential Astros reunion standing out among the reasons for Bregman to sign with a club. If he can’t re-sign in Houston directly, he might as well join his best ex-teammate on a Cubs team that is well positioned to win the NL Central.

We can discuss the merits of taking a short-term, prove-it deal in Chicago — Wrigley isn’t the best ballpark for Bregman’s metrics — but Bregman appears open to a more team-friendly contract structure, which should appease the notoriously stingy Jed Hoyer. The Cubs’ primary weakness in recent years has been a muted offense. Bregman and Tucker in the middle of the lineup would go a long way toward rectifying those concerns.

It could also convince Tucker to re-sign, even at a discount, if he gets to share Chicago with his buddy. Tucker and Bregman forged their relationship in the fires of World Series contention. That bond is quite significant when projecting Tucker’s (and Bregman’s) future. That would obviously stand in the way of Philadelphia luring Tucker to the east coast as a free agent.

Philadelphia can’t get deterred this early in the process. Bregman hasn’t even signed on the dotted line yet. If the gaggle of former Astros in Chicago adds one more, though, Dombrowski may need to start planning out his Kyle Tucker alternatives. Just in case.