Cubs Week in Review: Squad Set to Begin Wild Card in San Diego After Limping to Finish Line

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Being the flawed individuals we are, we have a tendency to let 'good' be the enemy of 'great'. Such is the case when discussing the 2026 Chicago Cubs. Not only did they clinch their second straight playoff berth last week, but they saw their center fielder become just the seventh player in MLB history to reach the 40-home run and 40-stolen base milestones in a single season. Despite these marks of excellence, however, the club's avoidable losses over the last seven days have the spirits of this team's supporters in the doldrums. Though there is much to be desired, make no mistake about it: this is a good team, and they've earned the right to keep playing.

Kicking off what could be the last three games at Wrigley Field in 2026, the Cubs welcomed Miami to town last Tuesday night. Left-handed ace Shota Imanaga toed the rubber for the North Siders, going five frames, allowing just one earned run and setting down seven Marlins via the strikeout. Early production from the top of the Cubs' lineup wasn't enough for the home team to break through with a serious momentum-shifting rally, though, leading to the heartbreak of what transpired in extra innings. With a chance to advance runners at first and second in the home half of the 10th inning, Matt Shaw (on maybe the worst bunt attempt in the majors this year) popped the ball up for the first out. That out might as well have counted for all three, as the lineup failed to recover from the ill-fated at-bat. A 12th inning bullpen blow up sealed the home team's fate in an 8-2 loss.

Trying to cleanse themselves of the previous night, Chicago trotted out veteran hurler Kevin Gausman to secure the squad's hotly-anticipated playoff berth. A cold night at the plate for the North Siders deferred that dream for one more night, as the spoiler-minded Marlins (led by slugger Kyle Stowers) prevailed once again. The Cubs wasted eight scattered hits, clearly laboring under the pressure of the attempt to realize a postseason champagne bath, and a chance at Crow-Armstrong making history. The Cubs dropped the series and the game in a 3-2 loss.

A rush of triumph has a way of absolving even the nastiest defeats of the past, and that's exactly the feeling that spread throughout 1060 W. Addison on Thursday afternoon in their regular-season home finale. Pete Crow-Armstrong handled the first order of record-setting business, swiping his 40th base of the campaign in the early going. With that weight lifted, the Cubs went to work, highlighted by a masterful seven-inning performance from Matthew Boyd, who searched for and squeezed out every ounce of resolve he could, like scraping the bottom of a bottle of giardiniera. With the plane to Boston waiting for them, Seiya Suzuki and his club basked in the glory of a hard-fought season they ensured would not conclude after game 162.

Threats of a dreaded Nor'easter pushed up the squad's three-game tilt with the Boston Red Sox, much to the chagrin of Counsell. The first half of a Friday twin bill saw an abbreviated outing from starter Clay Holmes, opposite Alec Gamboa of Boston. For a team that (at the time) was still playing for home field in the Wild Card round, Chicago looked like a frustrated, sleep-deprived club longing for winter's reprieve. After plating runs in each of the first two innings, the North Siders went scoreless the rest of the way, leaving eight men on base and delivering just 2-for-11 with runners in scoring position.

With the slate wiped clean for the second game of the doubleheader, the Cubs couldn't generate any of their own thunder with the storms creeping in. David Peterson was as good as you'd like him to be, especially heading into postseason play. He delivered five scoreless innings, issuing just two walks in the process. The 2-0 shutout for Boston was the capper on what had been a putrid stretch of appearances for this lineup at the plate during clutch moments. Forthcoming events from their playoff foe San Diego guaranteed that the first leg of Chicago's postseason run (and perhaps all of it) would occur on the road.

Optimists searching for reasons to remain in that camp found them in the series finale with the Red Sox in St. Petersburg, Florida. Back after his terrifying scare last week, Alex Bregman provided resounding, heartening evidence as to the type of game-changing player he is. Smacking two home runs and a double on a 4-for-4 day, Bregman resurrected the squad's offense at (hopefully) just the right time for the Cubs to hang around the postseason for an extended stay. Braxton Garrett got the lion's share of the work, with five full frames after Imanaga opened things. The 6-2 victory, though not material, was still encouraging from a rhythm and vibes standpoint. Counsell and his staff are clearly doing what they can to preserve the best of what this ball club has to offer.

Now, postseason baseball is here. At 9 PM Central time on Tuesday night, screens across the Chicagoland area will light up with the Chicago Cubs taking the field to begin their quest for the franchise's fourth World Series crown. This is what all 30 MLB teams play for, and though it may not always look like it, as of right now, the North Siders have a shot.