Cubs punched their Wild Card ticket but can't escape uncomfortable regular season reality

The Chicago Cubs are here again. The Cubs reached the playoff through means of stumbling into the fifth seed in the NL Wild Card race, and have a series against the San Diego Padres on deck. Considering the Cubs spent most of the season without Cade Horton, Justin Steele, and Ben Brown, making the playoffs certainly feels like an accomplishment.

But is that the reality the Cubs are forced to live with? Sharing the same division as the Milwaukee Brewers, have we reached the point where simply finding an invite to the dance is enough?

It shouldn't be and as a recently as last February, it wasn't. Tom Ricketts made it clear what the goal was this season, make the playoffs by winning the NL Central division.

“We want to win the division. We should win the division. We should be right there. You want to win the division for a lot of reasons not just because its aggravating not to – but you want to put yourself in the best position for the playoffs as well.”

By their own standards and expectations, the Cubs' regular season was a failure

Going line by line, did the Cubs win the division? No. Should the Cubs have won the division? No. Did they put themselves in the best position for the playoffs? No. They finished the regular season 14 games back of the Brewers.

Whether Jed Hoyer's end-of-season press conference is later this week or later this month, injuries can't be used as the excuse for why the regular season was a failure. Yes, it's remarkable that the Cubs found a way to the playoffs, considering the circumstances that unfolded during the regular season; but for what the goal was in spring training, the regular season was a failure for the Cubs.

The uncomfortable realilty is that injuries weren't the reason why the Cubs were once again out-classed by the Brewers. The Brewers are a machine and the only way for the Cubs to overcome that reality is to spend on expectation.

They started to do that last offseason, signing Alex Bregman to a contract worth $175 million. There was an expectation that came with Bregman's arrival. It's that same expectation that is needed when the Cubs address their need for pitching this offseason. It's time to step outside their comfort zone when it comes to their pitching pursuits.

Case in point, last offseason, the Cubs bowed out of the bidding for Dylan Cease once it reached $200 million. Certainly a steep price for starting pitching, but Cease spent most of the 2026 season as a Cy Young candidate in the American League.

The Cubs have taken gambles with their pitching, but when you do so in low-risk fashion, there's an immediate path to doom if things don't work out. That was the case with Edward Cabrera, Phil Maton, and Hunter Harvey. Yes, the Cubs gave up their top organizational prospect for Cabrera, but his track record with the Miami Marlins reeked of him being an unfinished product.

This offseason, if the Cubs' reality is going to change, they need seek expected results and be willing to pay for that expectation. In other words, for the pitching staff, find the equivalent to the Bregman signing last winter.

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