Chicago Cubs get brutal playoff task after flubbing end-of-season push

The Chicago Cubs have flown out to St. Petersburg, Florida for what—as things have turned out—is a meaningless final game of the season against the Boston Red Sox.

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On Saturday, the San Diego Padres clinched home field advantage in the National League Wild Card series with a win over the Arizona Diamondbacks. The Philadelphia Phillies, meanwhile, are still vying for the third Wild Card seed with the Arizona Diamondbacks, with their fate to be determined this coming last game of the regular season.

The Padres, by taking the top Wild Card spot, will have home field advantage over the Cubs throughout the three-game series (starting Tuesday evening at 9 pm CT). And if the Cubs do make it past the red-hot Padres, they’ll have to play three of five possible games in the next round in Milwaukee against the Brewers.

To say the least, this does not bode well for Chicago’s chances in the postseason. As a matter of fact, many are writing off the Cubs—who will, on top of everything else, have to fly cross-country to get to their series in San Diego—entirely.

A disappointing end

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This is, without question, a disappointing way to end a season that began with expectations of winning the NL Central Division and even with some World Series chatter floating about. But, ultimately, the situation in which they find themselves is of their own doing, with everyone from the players to the coaching and front office bearing responsibility. In mid-August, they had a 6.5 game lead atop the Wild Card standings, but played sub-.500 ball the rest of the way to facilitate the loss of that important position.

Even heading into the final two series of the season, the Cubs essentially had their fate in their own hands, but responded with a 1-4 run.

Michael Cerami of Bleacher Nation recently laid out the realities of the North Siders’ 2026:

“Not only did the Cubs fail to achieve their goal of winning the NL Central this year, but they also won fewer games than last season, entering the playoffs as a lower seed with no home-field advantage in Round 1. We can talk about all the injuries (and there were a LOT), but they came up short this year. And that stinks.

And now their path to the World Series is extremely challenging…

Moreover, it isn’t usually easy when the Cubs travel west under normal circumstances, but their recent travel schedule has been nuts: they just went from Chicago to Boston to Tampa Bay for Sunday’s meaningless regular-season finale against the Red Sox. And now they’ll have to fly all the way back across the country to San Diego for this series. Brutal.”

What’s ahead

The slightest sliver of optimism heading into Tuesday is that the Cubs hold a 5-1 edge over the Padres in head-to-head play this season, with a 2-1 record at Petco Park. They also have some potentially explosive lineup assets who could carry the team on their shoulders with a big series.

And that’s about it.

The Padres are 17-6 this September, the Cubs are 10-13. They also have a .625 winning percentage at home this season.

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