You don’t have to do much coaxing to get me to speak romantically about October. Whether it was watching Magglio Ordoñez send a walk-off bomb into deep left field under the lights of Comerica Park or witnessing the magic and moments of the 2016 Cubs World Series run, playoff baseball hits different. We’re not quite there yet, but it’s starting to feel that way. By the time you read this, Craig Counsell and the Chicago Cubs will have just one month of grind-it-out contests remaining to punch their playoff ticket. Wha happens after that, nobody knows. This past week was a missed opportunity to open things up a bit in the scramble for playoff seeding, but there were good things mixed in with the bad. Will this group provide us a lifetime of new memories, or force us to spend a lifetime wondering what could have been?
Enjoying the jubilation of their sweep over the Los Angeles Angels last Sunday, the North Siders traveled to San Francisco for the second leg of their West Coast road trip. Unfortunately, it looks like the Giants have this team’s number. It showed in game one of this three-game series. The first contest featured future Hall of Famer Justin Verlander taking the bump opposite surprise Cubs ace Matthew Boyd. Though Verlander spun one that was far from “Vintage JV”, his counterpart suffered one of his worst outings of the season, going just 5 1/3 innings and coughing up five earned runs to the Giants’ offense. For the North Siders, the struggles from inside the batter’s box persisted, leaving eight men on base. San Francisco took the opener, 5-2.
Things got uglier in the second game of the set. The 12-3 loss came on a night where the Cubs’ run-scoring opportunities came few and far between. On the other hand, Rafael Devers and his squad ripped the cover off the ball, slugging with tremendous efficiency. Wasting one of Nico Hoerner‘s few long balls of the season, and in his home state, Chicago failed to make up ground on the Brewers; the division slid fully and finally out of reach.
By the time the club got out of McCovey Cove, it was three steps forward, three steps back. As you’d expect, Shota Imanaga put his side in a reasonable position to win, going seven innings and punching out five batters. The North Siders stranded over 33 baserunners this week, though, and that same failure to knock in guys in scoring situations stymied them in the last game of the Giants series. But what actually spoke louder in this contest was the astonishingly poor performance of the bullpen. Closer Daniel Palencia could not put the ball where he wanted it, and swung the door wide open in the ninth inning for the Giants to deliver the knockout blow to the Cubs. The 4-3 defeat marked the first time in the 2025 campaign in which the North Siders were swept in a three-game series.
The Cubbies lifted their spirits after traveling to the Mile High City for the first of a three-game set with the MLB-worst Colorado Rockies. It’s been some time since they have enjoyed a no-drama victory. Things were no different in this one. Dansby Swanson and our favorite play, the home run, took center stage like a performer at Red Rocks. Offensive pop has become a puzzling rarity for the lineup in the second half of the season, but it came back with a vengeance in this tilt. Cade Horton helped his squad get out to a 9-2 lead with five respectable innings. In a throwback to their early-season woes, the bullpen was slightly rocked by the Rockies, giving up five runs and making things far more interesting than they should have been. All told, however, the relievers provided a sigh of relief to the faithful in securing a victory, 11-7 over Colorado.
A key piece of Chicago’s formula for success in 2025 has been the remarkable reliability of its back-end rotation pitchers (Ben Brown not included). Still getting up to cruising altitude after missing much of the season due to injury, Javier Assad has been admirable in his recent starts. Trouble is inevitable, yet somehow, Assad continues to build an eyebrow-raising reputation of resilience, as he can routinely get himself out of a jam. He tip-toed his way out of adversity like Tom Cruise in Mission Impossible. Making it possible for the pen to come in and slam the door shut in breathtaking fashion, Ian Happ delivered an RBI double. It was one of the most clutch hits I’ve seen since the season started in Tokyo. The Cubs guaranteed the series victory with a 4-3 triumph. One more word on the bullpen; This is a unique amalgam of veterans and youngsters, and if they pitch in the playoffs like they did in this one, they’ll beat whoever they face in October.
Before returning to the warmth and welcome of Wrigley Field, Boyd and the Cubs took the field in Denver for one more versus the Rockies. With a winning road trip already under their belt, could the North Siders pull off the bookend sweep?
No. Boyd, despite going six innings and striking out five, wasn’t sharp. Chicago went 2-for-8 with RISP. An early clutch knock from Seiya Suzuki put the weary travelers out in front 2-0 early. After trailing 5-2 for what seemed like a whole holiday weekend, Iam Happ launched a game-tying three-run bomb to left field, breathing new life into the group. Capping off what was a concerning week to say the least for the young fireballer, however, Palencia allowed the leadoff runner aboard in the home half of the ninth, and Mickey Moniak drilled a ball into the deep corner in right-field. It gave baseball’s worst team a salvage game, and gave the Cubs a stark reminder of what happens when you let even the most lowly of squads a chance to get off the mat. The North Siders dropped the last game of the trip, 6-5.
In the space I’m provided to recap each week of Cubs baseball for you, I attempt to uphold an air of optimism. But one thing I will never do is sell you on false hope. This squad faces adversity both externally and internally, but with the final month of the regular season upon us, with more sports options to divert our attention, they are still a team worth paying attention to. The last-minute warchest the team’s top decision-makers are building right now should provide all of the evidence you need to prove that this club is still chasing October romance, and has just about caught up to it once more.