Must Cubs beat Padres for season to be a success? ‘Philosophically’ speaking, yes

The 2025 Cubs won 92 regular-season games, the most on the North Side since 2018. Their plus-144 run differential ranked third in the major leagues. More important than either of those accomplishments, the Cubs made the playoffs — October baseball, the holy grail — for the first time since 2020.

They’ll host the Padres in a best-of-three wild-card series beginning Tuesday at Wrigley Field, where 40,000-plus will pack the joint and party like it’s 1984 or 2003 or 2016. It’ll be epic. It’ll be everything.

Until the Cubs lose, that is.

If they lose, that is. Relax, no one’s saying they will. Then again, no one’s saying they won’t.

On that uplifting note, a question: If the Cubs do fail to advance past the wild-card round, after having come up well short in their division race against the small-market Brewers, should this season go down in the books as having been a successful one?

“That’s a pretty hard question to answer,” shortstop Dansby Swanson said Monday before a team workout. “I’ve learned so much in my career and life, really, about just being able to be grateful and enjoy each and every moment, and that starts with today, being able to enjoy being here with the guys and getting prepped for what hopefully is a long and unbelievable postseason run.”

Translation: “Put me down for a non-answer.”

I put the same question to manager Craig Counsell, who scoffed at it as “deep and philosophical” before indicating that it reminded him of an old “Saturday Night Live” skit. Dollars to doughnuts Counsell was referring to “Deep Thoughts by Jack Handey,” a skit that appeared often in the 1990s, when the 55-year-old skipper was coming of age as a professional ballplayer.

“The philosophy of what [equals] success, I don’t know,” he said. “I mean, we’re trying to win the game. That’s as far as I’m getting, man. We’re trying to win [Tuesday]. I’m not thinking past that. That’s where I’m at. …

“You guys can decide that. Honestly. You guys write whatever you want [and] decide that. It’s not going to bother me.”

Translation: “I was more of a ‘Matt Foley, Motivational Speaker’ kind of guy.”

That’s OK. We don’t need the Cubs to answer this question for us, anyway. No, it’s not enough for the Cubs to grab a wild-card berth and then go over-and-out on their own turf against a foe with a lesser record. No, this season hasn’t been a success yet. The Cubs don’t get off that easy.

The well-heeled, well-positioned Cubs, who ought to be in World Series-or-bust mode a lot more often than they are, haven’t won a postseason game since the 2017 National League Championship Series, when they stole one, and only one, off the Dodgers, who romped in five games.

Before now, president of baseball operations Jed Hoyer hadn’t presided over a Cubs playoff appearance since stepping into Theo Epstein’s shoes after the 2020 mini-season. That didn’t stop chairman Tom Ricketts from sticking a contract-extension offer under Hoyer’s nose before the latter had even had a chance to underwhelm with minor roster tinkering at the 2025 trade deadline, but clearly Hoyer is ownership’s kind of executive. Hey, how’s that Kyle Tucker extension going? Oh, it’s not? Perfect.

If the Cubs lose to the Padres, though? That’s called front-office failure, folks.

Counsell is 1-8 in playoff games since 2018, all of them with the Brewers. That got him a record $8 million a year from the Cubs, with whom he has yet to prove, over one disappointing season and a second one as yet incomplete, that he was a game-changing addition to the club. Here’s Counsell’s opportunity to change that in forever fashion.

Before Counsell, Swanson was Hoyer’s highest-profile swing. He signed a seven-year, $177 million free-agent deal heading into 2023 and has been good, not great, with the Cubs, we’d all probably agree. Swanson would agree with that, too. Well, now’s his chance, too, to make his time here unforgettable.

Winning a little more is the least these Cubs could do, and, boy, could Chicago ever use the kind of October pick-me-up only a baseball team can deliver to a city. What have sports fans here had to latch on to? The Bears haven’t won a playoff game since 2010. Neither the Bulls nor the Blackhawks has won a true postseason series since 2015. The White Sox haven’t won one since 2005. The Sky did win one in 2022, a year after their championship, so we tip our beer helmets to them even though they’ve completely cratered since.

What do we have to sink our feelings into around here at the moment? Let’s see, ICE officers pepper-spraying protestors in west-suburban Broadview. Fatigues-clad federal agents taking individuals into custody downtown. More troops en route to Illinois via the Department of Homeland Security. And playoff baseball.

Yes, we have playoff baseball, too. And thank goodness for it.