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North Side Contributor
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Image courtesy of © Kirby Lee-Imagn Images

When it comes to finding something to do in Chicago, we have a plethora of options at our disposal. Sadly, however, watching Chicago Cubs playoff baseball in October has not been one of those options for several years. That could be changing very soon. Lockdown pitching (paired with an overdue offensive onslaught from the squad's biggest boppers) has the North Siders back to their old selves and racing back toward the front of the National League pack.

If you haven't checked out my comprehensive recap of Chicago's five-game chess match with the Milwaukee Brewers, where have you been? Though the Cubs still trail Milwaukee's best by a full 5.0 games, the North Siders proved that they could be one of the only true foils to Pat Murphy's upstart Crew. The helmet sundaes at Wrigley are incredible, but they're not supposed to be the best part of day baseball at the ballpark; the baseball is. That was not the case in the opener of that long series, as the Brewers employed their signature brand of fundamental baseball to dismantle Craig Counsell's squad. Milwaukee used a four-run eighth to put the Cubs away, on an anemic day of offense from the North Siders. "Cold one" didn't just describe what fans imbibed at Sluggers after the 7-0 loss, but also the feeling they were left with from a flat performance. 

Mother Nature desperately wanted the June 18 game between these sides not to be played—so much that she pushed it back a second time, nixing the nightcap of the doubleheader Monday and pushing it to Tuesday. With the Friendly Confines brimming with an eclectic mix of different shades of blue and "No. 23" Ryne Sandberg jerseys, the home team came through with its best day of baseball in 2025 so far. Matthew Boyd is one of the best pitchers in the league, and proved why in the first game of that twinbill. His stability out of the gate in a 5 2/3-inning outing allowed the Cubs' bats to get going early, without a sense of creeping dread. Utility master Willi Castro belted a three-run homer, which kept the home team out in front, while the bullpen slammed the door on Milwaukee's potent offense. Sweeter than anything on the menu at Tim Horton's, the squad's top prospect Owen Caissie launched a bomb to left-center field, which gave his team the much-needed insurance to push them over the finish line in a thrilling 6-4 victory.

Presented with the opportunity to pull off a doubleheader sweep of their pesky division rivals, the North Siders showed up in the championship-caliber form we've come to expect from them. Jameson Taillon had virtually zero rust to shake off from an extended stay on the injured list. Backed by a sensational, play-making defense, Taillon enacted Prohibition on the Beermakers over six five-hit innings. The offense continued to benefit from its youthful spark, as Caissie supported the efforts of his teammates Michael Busch and Nico Hoerner with a clutch RBI single. The team held on again, this time 4-1.

Chicago claimed a series victory (for the week and the season) in the penultimate contest of the five-game fight. The perpetually underrated Colin Rea looked good, collecting his 10th win of the campaign, while his offense clicked at the right moments. Matt Shaw's meteoric rise continued, unloading a thunderous, eighth-inning tank to the left-field bleachers. Though critics will argue that the series was less relevant due to the Cubs' substantial deficit in the division, the improved optics of the squad playing winning baseball cannot and should not be overlooked. After a 4-3 win, that felt like the biggest takeaway. 

In their final home game before embarking on a nine-game West Coast trip to close out the month of August, the Cubbies found out that good teams are good for a reason. Admittedly, they didn't help themselves much, stranding a dismaying 11 baserunners. The steady and consistent Shota Imanaga put in fine work, going seven innings, but it would be for naught. Despite the Crew's 4-1 triumph in this contest, this series largely heralded the Cubs' return to form, getting them ready for the season's definitive last five weeks.

Dr. Dre's so-called "Wild Wild West" has offered a calm harbor for the Cubs this season, at least in Southern California. Powered by a fundamental tandem of clutch pitching and timely hits, the North Siders picked up an award-worthy victory versus the Halos. The fanbase has collectively, at times painfully, waited for star center fielder Pete Crow-Armstrong to break out of his frustrating slump. In the most clutch, stirring fashion imaginable, Crow-Armstrong drilled a go-ahead solo shot over the wall in right field. It was the kind of cathartic, mental health-boosting release the young superstar and his adoring teammates knew was coming, and did not disappoint. The brilliant Mr. Gasolina himself, Daniel Palencia, slammed the door shut on the Angels in the home half of the ninth to collect the 3-2 victory for the Cubs. 

As the frustrations mounted a few weeks back, easy, relaxing wins came at a premium for the North Siders. But with the outstanding Cade Horton (7 punchouts) toeing the rubber in game two, the offense exploded back onto the scene in a style worthy of a Michael Bay action film. Not far removed from reclaiming his throne with a homer in the series's opening game, Kyle Tucker erupted with a multi-home run game, his first as a Cub. Counsell's squad clogged up the bases with more traffic than "The 101" and constantly made the Halos pay. The North Siders pummeled some shlubby Anaheim hurlers and danced to a 12-1 'W', but the biggest swing of the game came from Reese McGuire, who detonated a ball into right for his first-ever grand slam. Don't overlook the fact that the blast put his club up 6-0, but please do zoom in on the meaning of that swat. Sending the Cubs' dugout into an absolute frenzy, McGuire's dinger officially announced the return of this Cubs team as a contender in the chase for the World Series crown. The heavenly middle game versus the Angels earned the road warriors their third-straight series win. 

Arguably, no one played a bigger role for the Chicago Cubs' 2016 World Series run (and the good parts of their subsequent years, for that matter) than veteran righty Kyle Hendricks. "The Professor" was a calming presence in the clubhouse for years, and a shockingly viable starter even as his stuff began to erode. The final contest of this three-game set brought about the emotional reunion of the Angels' hurler with his former club. The Cubs chased him early, and although they couldn't add on to the four runs they pushed across in the first half of the game, another strong outing from Taillon (plus great work by the bullpen) secured a series sweep.

The wait is over. Playing some very good baseball, the best version of the 2025 Cubs we've gotten to know over 131 games this season is back. What we learned this week is that, yes, this is a playoff team, and no, opponents facing off against this club can not take anything for granted. The job is not done yet, but they're making quicker progress lately.


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