Chicago Cubs: Why the Cubs need to be watching the Philadelphia Phillies this winter

More News: Chicago Cubs: Kyle Tucker all but says goodbye in final comments of 2025 season

Most notable of the Phillies pending free agents are DH Kyle Schwarber, starting pitcher Ranger Suarez, catcher J.T. Realmuto, reliever David Robertson, and outfielder Max Kepler. This is a quintet that, according to Spotrac, could account for about $79 million in 2026 payroll.

But what does this have to do with the Cubs?

If the Phillies go all-in on pursuing Tucker– and actually sign him– they may have to say goodbye to most of their other free agent talent. Four of their five potential outgoing players would fit in nicely with the Cubs’ immediate needs.

The most nostalgic and eye-catching Phillies import would be Schwarber, of course.

How the Chicago Cubs could benefit from ex-Phillies

The Cubs World Series legend is still a beloved figure in Chicago and would be welcomed back to Wrigley Field with opens arms by the fans. He’d also be a welcomed asset to a Cubs offensive sure to be smarting from the loss of Tucker.

Schwarber will be 33 by opening day and won’t draw the kind of extended contract the 28-year-old Tucker will demand. As a bat-only player, he’ll also earn a more modest contract– likely in the neighborhood of $100-$130 million over four years rather than the 10-year, $400 million deal Tucker will be looking for.

What makes this Schwarber-to-the-Cubs situation unlikely is the fact that the Phillies seem very interested in re-signing the left-handed slugger. “Schwarbs” also seems to be harboring some read-between-the-lines bad blood when it comes to Cubs president Jed Hoyer, who non-tendered him prior to the 2021 season in a mind-boggling budget move over about $3 or $4 million in pending arbitration.

If the Phillies swing and miss on Tucker but re-sign Schwarber, the Cubs would still be wise to keep their eyes on them.

Who in Chicago wouldn’t want Ranger Suarez in the starting rotation if Philadelphia can’t hold on to him? Realistically, though, he may be too rich for the taste of the Cubs’ ownership. The 30-year-old is projected by Spotrac to land a 6-year contract worth about $161 million.

Value beyond the stars

If the Phillies do end up re-signing both Suarez and Schwarber, though, there’s still value to be found in the talent let go.

Philadelphia’s late season bullpen addition, Robertson, might be gone no matter what. The Cubs picking up the 40-year-old former closer on a budget one-year deal this offseason could be a smart and conservative Cubs-like bullpen move. Phillies outfielder Max Kepler could also be an emergency depth acquisition for a Cubs team without a “for sure” right fielder.

Right now, everything should be on the table for Chicago’s front office. Laying back and watching what the Phillies do could offer some guide as to the moves they make this offseason.