Red Sox-Cubs Reunion Suddenly Carries A Much More Serious Bregman Concern

With Bregman's injury casting doubt on his return, the Red Sox-Cubs series may miss a highly anticipated reunion.

Alex Bregman’s expected trip back to Fenway Park may have to wait.

The Chicago Cubs third baseman was supposed to be part of the final series of the season against the Boston Red Sox from September 25-27, setting up a reunion that would have carried extra heat after Boston lost out on him in free agency. Instead, Bregman’s status is now in doubt after a brutal injury on September 20 changed everything in an instant.

Standing near the on-deck circle and getting loose for his next at-bat, Bregman was struck in the face by a foul ball off Michael Busch’s bat. The ball came back on a line and caught him square in the cheek.

There was no time to get out of the way. He immediately covered his face with his hands and went down the dugout steps with a trainer.

Afterward, Bregman posted a photo of his face that showed a swollen-shut black eye and a bloodied cheek. He shared another image the next morning, and the entire left side of his face was swollen.

The Cubs took him to the hospital after the hit. Chicago manager Craig Counsell said Bregman was hit in the left cheekbone just under his eye and that his nose was bleeding.

Jeff Passan reported on September 21 that Bregman has multiple facial fractures and will not undergo surgery, though that does not necessarily mean surgery isn’t still needed. Passan also reported that Bregman hopes to return in the postseason, but he may be too banged up to make it happen.

For now, a return against Boston looks unlikely. With no official diagnosis yet, it is hard to imagine him getting back in time for the Cubs’ series at Fenway Park, and his availability for Chicago’s playoff run is also in question depending on how far the team advances.

Bregman had started slowly with the Cubs this season, batting .241/.336/.359 over 45 games before the All-Star break. After the break, though, he caught fire, hitting .296/.378/.600 in 44 games. He also hit 17 home runs in the second half, nearly doubling his first-half total of nine.

Outside of National League MVP candidate Pete Crow-Armstrong, Bregman had been Chicago’s most important offensive presence in the second half. Losing him now lands hard for a club trying to finish strong and keep its playoff path as favorable as possible.

The timing is especially rough with the National League Wild Card race still tight. The Cubs and San Diego Padres are tied for the first Wild Card spot, while the Philadelphia Phillies are one game back. Without Bregman, Chicago may have a tougher time securing the best possible position and could be pushed into a first-round matchup with a dangerous opponent such as the Los Angeles Dodgers or Milwaukee Brewers.

And for Boston, the injury means the Red Sox likely won’t get the chance to see Bregman back in their ballpark so soon after missing out on him in free agency.

In Other News...

Payton Tolle Just Gave Red Sox Fans Another Reason To Love Him

Payton Tolle had more than the usual rookie celebration in his pocket when the Red Sox wrapped up their postseason spot. The left-hander spent part of the clinch festivities speaking with reporters, and he came off as a pitcher who not only knows how far he has come since 2025, but also understands why Bostons run matters so much right now. His 2026 season has turned into a strong one, with a 9-6 record, a 3.02 ERA and 166 strikeouts across 25 starts.

For a club already looking ahead to October, Tolles growth has become another reason the fan base has taken to him so quickly. He did not sound like someone content to simply enjoy the moment, either, as he expressed optimism about the Red Soxs playoff chances and the kind of baseball this group can still play. For a team built around believing the next step is still possible, that kind of confidence from a young arm only adds to the intrigue. [Read more 🡒]

Red Sox Could Soon Face A Tough Garrett Whitlock Decision

Garrett Whitlocks future keeps circling back to the same question for the Red Sox: is he more valuable as a high-leverage reliever, or could he bring even more to the club if he moves into the starting rotation? Whitlock has the kind of pitch mix that can make the idea tempting, and Boston has long appreciated the versatility he brings to the staff. With his contract situation giving the team options for 2027 and 2028, this is the sort of decision that could shape not just his role, but part of the clubs long-term pitching plan.

The appeal is obvious, but so are the concerns. A move to the rotation would ask more of Whitlock physically, and health has to be part of the conversation whenever Boston weighs changing a pitchers usage pattern. For now, the Red Sox can keep exploring the possibility without rushing into anything, but the fact that the discussion is even on the table suggests this could become one of those strategic calls that defines how the roster is built in the seasons ahead. [Read more 🡒]

Red Sox Suddenly Face A Pre-Playoff Seeding Problem At Fenway

The Red Sox have already punched their ticket to October, but the final three games at Fenway Park suddenly carry a different kind of importance. Boston is set to close the regular season against the Cubs, and a significant storm forecast could put the schedule in flux just as the club is trying to settle into its playoff rhythm.

MLB may be forced into some awkward juggling if the weather knocks games off the board, with postponements and possible makeup plans creating the kind of late-week uncertainty teams prefer to avoid. Doubleheaders could enter the conversation, and so could the impact on rest before the postseason begins, leaving Boston with one more variable to manage before the real games start. [Read more 🡒]