3 Takeaways After the Cubs Score 10 & FINALLY Win a Baseball Game

The losing has finally come to an end on Wednesday night. But, wow, was that a brutal stretch of baseball for the Chicago Cubs! Since May 9th, when the Cubs had the best record in baseball at 27-12 and were on a 10-game winning streak, they have lost 14 of their last 16 games, falling to last place in the NL Central and out of the playoff picture.

Baseball, man.

With today's 10-4 win, the Cubs finally reach the 30-win mark on the season (30-26) and jump to 3rd place in the NL Central. Meanwhile, the Pittsburgh Pirates (29-27) fall to last place in the division. The Cubs will have a chance to break even in this four-game set with the rubber match tomorrow afternoon vs Paul Skenes. For now, though, let's appreciate a win – the Cubs' first since May 15th.

Ian Happ and Cubs bat breakout (FINALLY)

May 27, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs left fielder Ian Happ (8) hits a three-run home run against the Pittsburgh Pirates during the seventh inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

The Pittsburgh kid Ian Happ drove in five runs in the Cubs' 10-4 win over the Pirates. In a back-and-forth game, it was Happ's 3-run home run in the top of the 7th that kicked off a 6-run inning for the Cubs.

The Cubs' bats finally woke up after a deep, deep slumber that saw their team batting average dwindle down to .185 and drop even further with runners in scoring position during their 10-game losing streak (.110). The Cubs had only scored first twice during that slump, and Ian Happ was posting an unbelievable .065 batting average in his previous 30 plate appearances. But Happ bucked all of those trends with a clutch 2-run single in the 1st to open the scoring for the Cubs.

Right before Happ's 3-run home run, Alex Bregman dropped a ball into left field for a double, his 2nd hit of the game – seeing his hitting streak extend to 7 games now. Michael Conforto later followed Happ's home run with a 2-run shot to right-center field, traveling 395 ft. Good to see the pinch-hitting success return!

Everyone in the starting lineup but Moises Ballesteros got a hit tonight with Happ, Bregman, Nico Hoerner, Carson Kelly, and Dansby Swanson all with two hits for a total of 14! Now, it's time to work on sustaining and building off this success against Paul Skenes on the mound tomorrow.

Is Jameson Taillon Becoming a Liability

May 27, 2026; Pittsburgh, Pennsylvania, USA; Chicago Cubs starting pitcher Jameson Taillon (50) delivers a pitch against the Pittsburgh Pirates during the first inning at PNC Park. Mandatory Credit: Charles LeClaire-Imagn Images | Charles LeClaire-Imagn Images

Another so-so outing for Jameson Taillon, who came away with a no-decision in the Cubs' win tonight. While he did make it through 5 innings, it was a forgettable start from the veteran. Taillon allowed 4 runs on 5 hits with 2 walks and 4 strikeouts, which objectively isn’t an awful line, but all four runs were scored off two 1st-pitch home runs.

In the bottom of the 3rd, Taillon would walk the leadoff batter in Endy Rodriguez and allow Spencer Horwitz to reach on a single after falling behind 3-0 in the count. Brandon Lowe would step to the plate and crush a 1st-pitch inside fastball into the right field stands, tying the game at 3-3. Catcher Carson Kelly appeared to be looking for a high fastball, Taillon threw it low and inside, only for Lowe to hit his 3rd home run off Taillon this season.

It felt like a back-breaker.

Especially because the Cubs had just jumped out to an early 3-0 lead, which made the Konnor Griffin solo home run the following inning even more frustrating. He smashed a 1st-pitch 92 mph fastball inexplicably located in the top left corner of the zone. The solo shot tied the game at 4-4 and came off the heels of what was then the go-ahead RBI double from Pete Crow-Armstrong in the top of the 4th.

Taking a look at Taillon’s 75 pitches tonight, only 29 pitches were located in the strike zone, and of those 29 pitches, only 20 were called strikes. Taillon didn’t have great stuff tonight, and it felt like his control was lacking when he did get some bite on his breaking pitches. But he was lucky he faced a Pirates lineup that doesn’t have many bona fide bats yet.

The Cubs don't really have a choice; they have to keep relying on Jameson Taillon despite allowing two more home runs for a league-leading 19 on the season. The Cubs did get some positive news on both Justin Steele and Matthew Boyd yesterday, but Taillon has to eat innings for the Cubs this year if they plan to work their way back into the playoff picture.

Giving Jacob Webb his flowers

May 12, 2026; Atlanta, Georgia, USA; Chicago Cubs pitcher Jacob Webb (71) throws against the Atlanta Braves in the seventh inning at Truist Park. Mandatory Credit: Brett Davis-Imagn Images | Brett Davis-Imagn Images

After the five iffy innings from Jameson Taillon, Jacob Webb entered the game in the 6th and gave the Cubs a shutdown inning. He struck out the side on 17 pitches, throwing 12 strikes. Webb attacked the Pirate hitters, and while Konnor Griffin did put up a fight in a 9-pitch at-bat for the final out, Webb set up Happ and the Cubs to take the lead in the top of the 7th with his scoreless frame.

With another scoreless outing, Webb has put together an impressive streak of games. Today marked his 7th straight scoreless inning of work. And with his three punch outs this evening, it was the 4th time in his last 7 games he's registered two or more strikeouts. He's allowed just one run so far in May while striking out 15 batters and only issuing two walks, dropping his ERA from 4.26 to 2.66 on the season.

Jacob Webb earned the win today. This might be seen as an outdated stat in the modern era of baseball, but after going 10 straight games without one, it was the only stat that really mattered today for the Cubs.

That's right! Breathe easy, friends – the Cubs have finally won a baseball game!

Sign up for our free newsletter to stay up-to-date with all things Chicago Cubs.

Add us as a preferred source on Google