Cubs Week In Review: A Wild Card Test In San Diego Awaits 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 baseball team. Not only did they clinch their second straight playoff berth this past week under manager Craig Counsell, they saw their center fielder become just the seventh player in MLB history to reach the 40 home run and 40 stolen bases milestone in a single season. Despite these marks of excellence, the club's alarming penchant for "go quietly into the night" losses akin to what we witnessed in the last seven days has the spirits of this team's supporters in the doldrums. Though there is much to be desired, make no mistake about it: there is more baseball to be played.

Kicking off what could have been the last three games at Wrigley Field in 2026, the Cubbies welcomed Miami to town for the opener of their tilt with the Fish. Left-hander Shota Imanaga toed the rubber for the North Siders in this one, going five frames, allowing just one earned run and setting down seven Marlins via the strike out. 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, leading to the crushing 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 foul stench left lingering from the previous night, Chicago trotted out veteran hurler Kevin Gausman out on the mound to help secure the squad's hotly-anticipated playoff berth. A cold night at the plate for the North Siders deferred that dream for another day, as the spoiler-minded Marlins, led by the scrappy Kyle Stowers, prevailed at the Friendly Confines 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 sins of the past, and that's exactly the feeling which emanated throughout 1060 West Addison on Thursday afternoon in their series' finale with the Marlins. Pete Crow-Armstrong handled the first order of record-setting business, by 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 repeatedly searched for and squeezed out every last ounce of resolve he could. 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 Cubs' skipper Craig Counsell. The weather did not permit, setting up the first of a doubleheader with the boppers from Beantown. The first of the twin bill saw an intentional 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 arguably 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 shut out 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 as such found them in the series' finale with the Red Sox in Saint 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 homers and a double on a 4-for-4 day, Bregman resurrected the squad's offense at a time that is hopefully just the right one for the Cubbies 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 up. The 6-2 victory, though not material in many ways to what lies before this team, 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.

And now postseason baseball is here. At 9pm Central Time on Tuesday night, millions of screens across the Chicagoland area will light up with the Chicago Cubs taking the field to begin their quest at seizing 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.