The Cubs have reached the final week with their October ticket nearly punched, needing either one more victory or one Arizona loss to lock up a National League Wild Card berth. The opponent and site for that opening round remain unsettled, but Chicago’s larger question is already in view: can this roster find enough late-game pitching and lineup length to survive a crowded National League field?
With six regular-season games left, the Cubs are trying to line up a postseason staff behind a club that has leaned heavily on Pete Crow-Armstrong’s remarkable all-around season. The Brewers, Dodgers and Braves are among the contenders standing between Chicago and its first World Series appearance since 2016, and the Cubs’ margin for error will shrink quickly once October begins.
The ninth inning remains Counsell’s biggest puzzle
Manager Craig Counsell has used 14 different pitchers for saves this season, a measure of both the bullpen’s flexibility and its unsettled finishing order. Jacob Webb leads the team with nine saves, but Daniel Palencia has recently pushed himself back into the late-inning conversation.
Webb was nearly untouchable for a long stretch, making 24 consecutive scoreless appearances from June through August. His recent work has been far less stable: he has surrendered 11 runs across his last 7 2/3 innings, spanning nine outings.
Palencia, a former closer, has thrown 6 1/3 scoreless innings in a row and delivered two scoreless frames in one of his strongest appearances of the year. Chicago entered its series in Cincinnati having converted only four of its previous 12 save chances, making the search for dependable late outs more urgent.
Trade-deadline addition Ryan Zeferjahn and left-hander Ryan Rolison could also be part of Counsell’s late-game mix. But the potentially most intriguing relief option is Edward Cabrera.
Cabrera’s bullpen move could change the equation
Cabrera returned on Sept. 15 after another blister issue on his pitching hand, and the Cubs have shifted him into a multi-inning relief assignment for the stretch run. The club hopes shorter appearances will help keep him available while possibly adding a little life to his velocity.
His initial bullpen appearance was uneven, as he allowed two runs in 2 1/3 innings. He followed it with a much cleaner outing Sunday, needing only nine pitches to work a scoreless inning.
The Cubs are hoping the temporary transition unlocks a high-impact October weapon, much as Roki Sasaki did for the Dodgers. Cabrera’s starting season has been difficult, with a 5.68 ERA in 15 starts and three injured-list stints, but there is still time for him to become a meaningful part of the relief corps.
Crow-Armstrong has carried the offense, but October needs a full lineup
Crow-Armstrong’s Sunday homer pulled him even with Philadelphia’s Kyle Schwarber for the Major League lead. The Chicago center fielder has been the centerpiece of the Cubs’ lineup, leading the club in average (.280), home runs (45), RBIs (107), stolen bases (38), runs (118), on-base percentage (.371), hits (170), triples (eight) and games played (156).
It is the kind of season that has placed Crow-Armstrong at the front of the National League MVP discussion. Still, postseason pitching does not permit one player to carry an offense alone. Chicago will need Seiya Suzuki, Dansby Swanson, Ian Happ, Alex Bregman and Michael Busch to create traffic and turn Crow-Armstrong’s production into sustained scoring.
The rotation starts with Holmes and Boyd
Clay Holmes and Matthew Boyd stand as Chicago’s clearest top two postseason starters, though Counsell has not named a Game 1 pitcher. Holmes looked ready to claim that role after returning from a right fibula fracture that sidelined him for nearly three months. In August, he posted a 1.55 ERA in five starts.
September has been a different story. Holmes has allowed 16 earned runs in 15 1/3 innings over three starts, good for a 9.39 ERA during the month. For a team without unlimited starting-pitching depth, that late stumble is a concern heading into the playoffs.
Shota Imanaga has regained steadier footing after a difficult August, while veteran Kevin Gausman gives Counsell an experienced arm capable of covering multiple innings in whichever postseason role is needed. The Cubs are close to clinching, but their October identity will depend on whether those arms—and a bullpen still looking for a closer—can hold leads for an offense built around Crow-Armstrong.



