A strike from victory, bullpen issues cost the Chicago Cubs a 4-3 loss to the Milwaukee Brewers in 10 innings

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MILWAUKEE — For two months, Jacob Webb was nearly untouchable.

Webb became a stabilizing force in the Chicago Cubs’ bullpen when a banged-up pitching staff needed the veteran reliever-turned-closer the most. His stretch of 24 consecutive scoreless outings between June 24 and Aug. 21 helped establish the team as one of the best in the National League.

The last 2 ½ weeks have been a different story.

Webb found himself in a position that has become too familiar. Two costly changeups turned into another blown save and loss for the Cubs on Tuesday night at American Family Field when Webb, one strike away from locking up a win, gave up a single to Christian Yelich, then two pitches later watched Jackson Chourio take him deep for a game-tying two-out, two-run home run in the bottom of the ninth.

Carson Kelly had appeared to be the hero in the ninth, delivering a pinch-hit two-run double with the bases loaded against Brewers closer Trevor Megill. But the Cubs failed to score in the top of the 10th — hurt by Seiya Suzuki over sliding third base on a tag up for the second out — and Luis Lara’s bases-loaded single off lefty Caleb Thielbar in the bottom half of the frame handed them a 4-3 walk-off loss.

In his last six outings since the end of his scoreless innings streak, Webb has allowed nine runs, including three home runs, in 4 2/3 innings. Chourio’s home run was the first Webb allowed on his changeup since June 10 and just the third of the season against the pitch.

“I’m tired of letting the team down, to be completely honest,” Webb said afterward. “It’s pretty tough to watch every time I give up a homer.”

Holding on for the win would have moved the Cubs (81-65) above the Phillies for the first wild-card spot in the National League; instead, they enter Wednesday’s series finale riding a three-game losing streak. The bullpen faltered for a second consecutive day, part of a tough stretch for the group that largely has held it together since the All-Star break (3.80 ERA entering Tuesday, 13th in the majors).

“This is how you have to win games in the bullpen, you’ve got to get outs,” manager Craig Counsell said. “It’s our job, they’re going to do it. It hurts when it happens. It hurts when it happens consecutively, but we’ve got nine guys down there. They’re the ones we’re going to rely on and we’ve got to figure it out.”

The Cubs’ offense had the tough challenge of again facing NL Cy Young Award contender Jacob Misiorowski, who allowed a lone run over 6 1/3 innings on Michael Busch’s RBI single in the first. That lead was brief as Brice Turang responded in the bottom half with an RBI single against left-hander David Peterson.

Peterson did enough to work around traffic on the bases, holding the Brewers to one run on six hits and three walks in 4 1/3 innings. Four strikeouts and two double-play balls aided that effort. Right-hander Aaron Civale gave the Cubs two big shutout innings in the sixth and seventh, striking out four of the six Brewers he faced.

For as much as the bullpen has been getting it done this season, weaknesses and regression have been exposing the unit. The Cubs have relied on a mix of pitchers taking on new roles as their projected top relievers have dealt with injuries most of the year, particularly to high-leverage options Daniel Palencia, Phil Maton and Hunter Harvey.

Asked whether changes need to be made to the Cubs’ bullpen by calling on options at Triple-A Iowa, Counsell replied, “The answers are not there, I mean, we can’t do it.”

“These are our guys,” Counsell continued. “They’re going to get the outs. You go through tough stretches in the season. It hurts when it happens right now, it hurts when it happens right at the end of the game with two outs, hurts a little bit worse. And it tests you and you have to use the test and you have to use the hurt to get you to a better place, and it can. When you get knocked down and you can get back up, that’s an even better feeling.”

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The playoffs beginning in three weeks adds to the uneasiness of the bullpen’s performance over their last 17 games, featuring a 5.40 ERA in that span. Perhaps the Cubs, attempting to be judicious in the veteran’s return from a second Tommy John surgery, would be better served continuing Shelby Miller’s build-up in the majors to add velocity to the bullpen rather than on his rehab assignment at Triple A. Left-hander Justin Steele is scheduled for his third rehab outing with Iowa on Thursday, but the Cubs aren’t sure what his impact might be down the stretch.

If anything, the Cubs’ recent bullpen implosions are more of an indictment of the organization’s inability to develop high-leverage arms from within their farm system.

Palencia, coming off an electric 2025, had this year hampered by two injuries and hasn’t been able to recapture his explosive fastball or confidence on the mound. Porter Hodge delivered a 1.88 ERA in his 2024 rookie season but struggled last year (6.27 ERA) and missed this season following elbow surgery. They ultimately gave up on hard-throwing lefty Luke Little by designating him for assignment in August after the 26-year-old showed promise with a 3.46 ERA over 30 appearances in 2024. Pitching prospect Jaxon Wiggins, slowed by elbow inflammation early in the season, hasn’t become a late-season viable arm out of the bullpen.

Bullpens can be notoriously volatile and difficult to project year-to-year. The lack of internal options at this point of the season, though, adds to the uncertainty of what this group can provide in the postseason. They’ve got three weeks to figure it out.

“We’re gonna get back on track,” Webb said. “I have confidence in myself. I have confidence in this team, the bullpen, the pitching staff, the hitters. I’m just tired of letting the team down right now. It’s piss poor.”