Are you ready for both the Cubs and the White Sox in the playoffs?
For God’s sake, somebody has to be.
Are the Cubs themselves ready? It’s a bit hard to believe in that after they spent the final days of the regular season losing back-to-back critical games at Wrigley Field to the going-nowhere Marlins, then gagging on both ends of a doubleheader in Boston, to rob themselves of a sweet chance at home-field advantage in a wild-card series against the Padres that starts Tuesday.
Instead, off to San Diego they went after a meaningless 6-2 win Sunday against the Red Sox in St. Petersburg, Florida — look, don’t ask — a 2,000-plus-mile flight during which a travel-weary Cubs team was left to wrestle with some uncomfortable questions.
“Can we hit anymore?”
“If we have an ace, where might he be hiding?”
“Bullpen? What bullpen?”
And then there are the Sox, who are as experienced at playing postseason baseball as the average bob of seals is at filming TikTok dances. They’ll be in Houston, also starting Tuesday, against a .500 Astros team that owns the distinction of being the worst division champ, by record, in major league history. Despite that, the Sox are the betting underdogs, presumably having something to do with the fact they lost approximately 8.4 billion games from 2023 to 2025.
Unlike the 89-win Cubs, though, this year’s 84-win Sox finished strong, winning back-to-back-to-back series against the Tigers, Royals and Rockies. Alas, it wasn’t enough to out-sprint the Guardians to the finish line for a division title simply because the Guardians woke up one mid-September morning having inhabited the bodies of the 1927 Yankees. Maybe this is Cleveland’s year to end the majors’ longest current World Series championship drought? It would be a shocker, but it’s possible.
The Sox, on the other hand? Bless their hearts, they’re just babies.
Still, you might as well take everything you’ve read thus far in this column, wad it up and drop-kick it onto the nearest trash pile, because this is no time for negativity. It’s only the fourth time both Chicago teams have made it to the postseason, which makes this a mighty big occasion. And can’t we all agree our city was home to baseball’s best two stories this season — the out-of-nowhere emergence of the Sox and the all-out explosion of Cubs MVP-to-be Pete Crow-Armstrong?
What a thing these Sox have pulled off. Back on Opening Day in Milwaukee, I watched them lose 14-2 to the Brewers and thought: Here we go again. But even though general manager Chris Getz and manager Will Venable wouldn’t talk then about what improvement would look like in terms of a number of victories, some around the team were openly confident. TV analyst Steve Stone, a self-described psychic, told me the Sox were going to win “well above” outside expectations. Radio analyst Darrin Jackson thought 80 wins was possible. And second baseman Chase Meidroth had the temerity to use the P-word — “playoffs” — freely.
“We’re going to compete our asses off,” Meidroth said then.
I didn’t buy any of it.
Yeah, well, go suck an egg, Greenberg.
Despite Getz going in on starting pitcher Luis Castillo at the trade deadline — a failed move — the Sox’ season has been a success no matter what happens against the Astros or, if the Sox actually survive that series, against the Guardians after that.
Not so for the Cubs, who won’t have anything compelling to hang their hats on if they don’t advance further in Craig Counsell’s third year as manager and Jed Hoyer’s sixth year as president of baseball operations than they did in 2025.
Last season’s Cubs were good enough to beat the Padres in the wild-card round at Wrigley, but they couldn’t measure up to their prime tormentors, the Brewers, in the divisional round after that. This year, the richest team in the division finished so far behind the small-market Brewers — 14 games — it might take all the gumption the Cubs have just to show their faces in Milwaukee should they get past the Padres again.
The Cubs were 10-13 in September, but they’ve been less than impressive for a lot longer than that. Over the last four and a half months, they’ve been essentially a .500 team.
It won’t be as painful in San Diego as the last time the Cubs played playoff baseball there — yep, 1984 — but I don’t think they’ll make it to Milwaukee. An underwhelming season is nearing the end.
I’ve got the Astros in three, too.
Either that or a Red Line World Series, right?
Here we go.
