Takeaways After Cubs Spiral at Worst Time and Lose Two Straight to Red Sox

Just start the playoffs, already.

The Chicago Cubs (88-73) lost both games to the Boston Red Sox (87-74), dropping the first game 4-3 and then getting blanked in the afternoon game 2-0. The losses nearly confirm that the Cubs will be playing their three-game Wild Card series away from Wrigley Field. They will need a win on Sunday and for the Padres to get swept by the Diamondbacks to secure home-field advantage.

Regardless, a rough final week of the season will come to an end on Sunday in Tampa Bay, with both teams relocating from Boston due to nasty storms on their way to the East Coast. Sadly, the Cubs are limping into the postseason with a 10-13 record this September.

Overall, there was not a lot of good from either of these two games, but it was encouraging to see Alex Bregman return to the lineup as a DH in the first contest, despite him going 0-for-4 with a strikeout. At this point, the Cubs' focus should be to try to get as healthy as possible for Tuesday – no matter where they play.

The Cubs power is non-existent right now

Sep 25, 2026; Boston, Massachusetts, USA; Chicago Cubs first baseman Michael Busch (29) hits a single during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | IMAGN IMAGES via Reuters Connect

After two games in Boston, Tyrone Taylor is the only Cub with an extra-base hit – stop me if you've heard this story before. The Cubs' bats failed to string together hits on Friday, struggling to produce the big knock needed in either game to take control. The Cubs did score off Taylor's double in the first inning of Game 1, but only managed singles for the remaining 17 innings they played on Friday.

A total of 14 hits on the day, seven in each game, the Cubs went 2-for-15 with RISP across both games, stranding 14 batters in total on the bases. The Cubs walked five times today, but only once in the final game. The bats went cold after the second inning of Game 1 and felt like they accepted their fate in Game 2.

Craig Counsell recapped both games in his postseason session with the media, pointing out that the weather was a factor in the Cubs' doubleheader losses.

Craig Counsell addresses the media after the Cubs were swept in today's doubleheader: pic.twitter.com/dVUUHvPGoy
— Marquee Sports Network (@WatchMarquee) September 26, 2026

Credit to Boston's pitching after a bullpen game to open the doubleheader and then using just two pitchers in the second game. However, the Cubs' sudden lack of power as of late is a concern. This is especially true when we consider the Cubs' numbers over the last 30 days, where they've ranked 3rd in home runs (41) & RBI (139), 5th in walk rate (10%), 2nd in strikeout rate (18.4%), and 1st in team fWAR (6.8). They should have been better in these two games.

A poorly timed bad week from the offense reminds us how important it is for the Cubs to be the offensive powerhouse they've been at times this season. Their bullpen can't be relied on to maintain leads, and this off-week has cost the team a chance at hosting a playoff series.

Cubs starters are inspiring confidence

Sep 25, 2026; Boston, Massachusetts, USA; Chicago Cubs starting pitcher David Peterson (19) pitches during the first inning against the Boston Red Sox at Fenway Park. Mandatory Credit: Bob DeChiara-Imagn Images | IMAGN IMAGES via Reuters Connect

Clay Holmes, David Peterson, and even Javier Assad looked good. Peterson, in particular, is making a strong case to get a playoff start should the Cubs advance past the Wild Card series.

David Peterson’s last four starts:

4.1 IP | 6 H | 1 R | 3 BB | 4 K
6.0 IP | 3 H | 1 R | 3 BB | 7 K
6.0 IP | 3 H | 1 R | 1 BB | 7 K
5.0 IP | 3 H | 0 R | 2 BB | 6 K

A 1.27 ERA over that span has been HUGE for the Cubs down the stretch 🐻 pic.twitter.com/AD6rcMoTnJ
— Just Baseball (@JustBB_Media) September 25, 2026

The left-handed Peterson threw five innings of three-hit baseball with six strikeouts, allowing zero earned runs. He's been nails in his last four starts, allowing one run or less in all four with 6+ strikeouts in Peterson's last three starts.

Holmes only went 4.1 innings, allowing three runs (two earned) on five hits. He was pulled with runners on first and second in the bottom of the fifth. It wasn't a super clean outing, as only going 78 pitches in a doubleheader was not what Craig Counsell wanted to see. I actually wouldn't mind Holmes being pushed to the bullpen, especially in the upcoming Wild Card series.

Having experience as a starter in the playoffs and as a closer in the World Series is a huge plus for both sides and could help offset some of their bullpen deficiencies.

Off-Day Saturday, season finale in Tampa Bay

Sep 25, 2026; Boston, Massachusetts, USA; Chicago Cubs center fielder Pete Crow-Armstrong (4) steals second base ahead of the throw to Boston Red Sox second baseman Nick Sogard (20) during the fifth inning at Fenway Park. Mandatory Credit: Gregory Fisher-Imagn Images | IMAGN IMAGES via Reuters Connect

With the doubleheader on Friday, the Cubs will have an off-day on Saturday before playing their season finale with the Red Sox in Tampa Bay to avoid the Nor'easter coming to the Boston area.

I'm interested to see if Justin Steele will get a chance at a rehab start. He did travel to Boston and will likely be a part of the team in an unofficial capacity through the rest of the playoffs. It's likely out of the question to expect Steele to come back to the Cubs and pitch meaningful innings in the postseason ... but, boy, would that be fun!

It's also a massive boost to the Cubs' arms to see their former staff ace back and competing. But realistically, I simply want to see Steele in a major league game in any capacity. We can save the Kyle Schwarber 2016 comparisons for another article.

As for the current NL Wild Card standings, the Padres are close to clinching the top Wild Card spot. This means that if the Cubs finish in second place in the Wild Card, they will head to San Diego for a rematch of the 2025 Wild Card series. If they fall to third, they would head to Atlanta to face the NL East division champion Braves.

We'll see how Saturday shakes out and if the Cubs truly have something to play for on Sunday, or if their playoff destiny has already been decided.

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