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Cubs Bullpen Concerns Reach Boiling Point in Walk-Off Loss to Brewers

Another bullpen meltdown in the 9th allows the Brewers to walk off the Cubs in the 10th
Sean Sears|
Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs pitcher Jacob Webb reacts after giving up a walk off home run against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images
Aug 25, 2026; Phoenix, Arizona, USA; Chicago Cubs pitcher Jacob Webb reacts after giving up a walk off home run against the Arizona Diamondbacks at Chase Field. Mandatory Credit: Mark J. Rebilas-Imagn Images | IMAGN IMAGES via Reuters Connect

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Chicago Cubs

Jacob Webb was one out away from closing a 3-1 win for the Chicago Cubs. One changeup later, the game was tied.

The Cubs (81-65) dropped another one to the Milwaukee Brewers (90-56) in a 4-3 extra-inning loss. The Brewers responded to the Cubs each time they scored, with the Brewers never leading until they won the game in the bottom of the 10th.

A tough loss for the Cubs, who saw another win slip through the hands of their bullpen. Thankfully, the Phillies lost as well and remain just a half-game up for the final Wild Card spot. Nevertheless, the Cubs now sit nine games back of the top spot in the division, meaning their focus must shift to home-field advantage in the Wild Card series.

Here are three takeaways from the Cubs' 4-3 extra-innings loss to the Brewers on Tuesday night in Milwaukee.

Confidence level in bullpen at all-tiime low

Chicago Cubs pitcher Jacob Webb
Chicago Cubs pitcher Jacob Webb (71) watches a two-run home run by Milwaukee Brewers left fielder Jackson Chourio during the ninth inning of their game Tuesday, September 8, 2026 at American Family Field in Milwaukee, Wisconsin. | USA TODAY Network via Reuters Connect

It's another blown save for Jacob Webb, marking his 7th of the year, after he was only one out away from notching his nine save of the year. Webb was able to strike out Joey Ortiz and retire Garrett Mitchell on one pitch, but Christian Yelich pinch-hit for Cooper Pratt and got on with a single. Jackson Chourio stepped up to the plate and fouled off the first change-up he saw, only to send the second one into the left-field seats, tying the game 3-3 in the bottom of the ninth.

The 22nd home run of the year for Chourio was a no-doubter, crushing all the momentum the Cubs had built up in the previous half-inning. Caleb Thielbar would enter in the 10th but would only register one out despite facing four batters, allowing two singles, including the walk-off hit from Luis Lara.

Since August 1st, only the Mariners have had a worse bullpen than the Cubs, with a 0.5 fWAR. The Mariners are also the only bullpen with a higher HR/FB than the Cubs' 16.1 percent since August 1st, as well.

The Cubs lack swing-and-miss in their bullpen and recently haven't been able to work out of jams with runners on base. And with one clear-cut lockdown arm in the bullpen, Craig Counsell has been trying different arms in tough moments. Regardless, when asked whether or not he trusts this group of arms, the Cubs skipper preached confidence.

On that note, Aaron Civale and Ryan Rolison gave the Cubs some clutch innings, Civale covering the 6th and 7th inning, while Rolison had one of the biggest strikeouts of the game to end the 8th inning.

But with three weeks left in the regular season, now is not the time to be working through bullpen roles, especially in the midst of a Wild Card chase.

Bottom of the lineup puts up a goose egg

Chicago Cubs second baseman Pedro Ramírez
Chicago Cubs second baseman Pedro Ramírez (75) hits an infield single during the ninth inning of their game against the Milwaukee Brewers Tuesday, September 8, 2026 at American Family Field in Milwaukee, Wisconsin. | USA TODAY Network via Reuters Connect

The Cubs offense only managed seven hits, and three of those came in the top of the ninth inning. Jacob Misiorowski added another solid start to his Cy-Young campaign, striking out nine Cubs in 6.1 innings.

The Cubs managed to load the bases for Miguel Amaya, who was pinch-hit for by Carson Kelly. The catcher delivered in the moment, driving a ball off the wall and giving the Cubs a 3-1 lead in the top of the ninth. Kelly's go-ahead hit was the Cubs' lone hit coming from the bottom half of their lineup.

Alex Bregman, Ian Happ, Matt Shaw, Tyrone Taylor, and Miguel Amaya all went 0-fer, and only Kelly and Seiya Suzuki had extra-base hits. It was always going to be a tough night to score runs regardless, but the Cubs are struggling to score runs when Bregman, Suzuki, and Crow-Armstrong don't drive the offense. Not surprisingly, the Cubs are 6-13 in games that trio doesn't drive in a run.

And when Happ, Shaw, and Amaya combine for 7 strikeouts, along with the top of the lineup driving in zero runs, the Cubs aren't going to win many of those games.

Suzuki giveth and Suzuki taketh

Chicago Cubs right fielder Seiya Suzuki (27) is tagged out by Milwaukee Brewers shortstop Joey Ortiz (3)
Chicago Cubs right fielder Seiya Suzuki (27) is tagged out by Milwaukee Brewers shortstop Joey Ortiz (3) during the tenth inning of their game Tuesday, September 8, 2026 at American Family Field in Milwaukee, Wisconsin. | USA TODAY Network via Reuters Connect

Seiya Suzuki had an up-and-down night in Milwaukee. A major high was this amazing throw to home plate that kept the game tied 1-1.

It was a great throw from Suzuki to give Amaya a chance to grab the runner at home, but an even more impressive effort from Amaya to reach and tag the runner. It was also Suzuki's 8th assist of the season, which would be a career high for the gold-glove candidate.

Suzuki had a low on the base paths, however, getting thrown out at 3rd trying to advance on a fly ball in the top of the 10th.

The Brewers turned the double-play after Suzuki was unable to remain on the base. It was a back-breaking moment for the Cubs as the Brewers and their fans were visibly amped up after the play. Former Cubs infielder Jason Kipnis didn't love Suzuki's aggressive base-running in the moment, discussing it on Marquee's postgame show.

Kipnis is 100 percent right: This Brewers team does not beat itself and thrives on teams making mistakes. Suzuki gambled in a moment he really didn't need to and cost the Cubs a scoring chance in the top of the 10th.

You hope games like these are learning moments for a Cubs team that still has playoff hopes. But some of the Cubs' concerns are more serious than baserunning gaffes, and right at the top of that list is the bullpen. Fans will be watching for names like Edward Cabrera and Shelby Miller to be added to the group soon, but Counsell has three weeks to find his guys before the playoffs start.

Not ideal but that's baseball, or so they say.

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Published
Sean Sears
SEAN SEARS

Sean Sears is a contributor for Sports Illustrated Cubs who previously wrote for NBC Sports Chicago and FanSided. He also worked as a producer at 104.3 The Score, running baseball shows like Hit & Run and Inside the Clubhouse. A graduate of Iowa State University, Sean lives in Chicago’s Lakeview neighborhood and spends his free time walking his dog around Wrigley Field and listening to Cubs games from his patio.

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