4 questions the Cubs should be forced to answer after unceremonious Wild Card exit

If the Chicago Cubs want make sincere changes this offseason, it's start with finding answers to the questions that Jed Hoyer, Carter Hawkins, and Craig Counsell refuse to answer. Tom Ricketts is probably included in that group as well, but after he green-lit the team spending nearly $250 million this past season, it feels like he deserves a lesser share of the blame.

The Cubs are more than halfway through Counsell's five-year deal and there's very little to show for it. Sure, Counsell managed the Cubs to the playoffs in each of the last two years, but it feels like the Cubs reached October each year out of gas.

Here are the hard questions that need to be asked if the Cubs truly want to get to the bottom of their incompetence

2026 was meant to be the "if not now, when" season for the Cubs. Instead, they were 14 games back of the Milwaukee Brewers in the National League Central, backed into the playoffs with a record of 11-13 in September, and it's hard to point to any reason why that expectation should change in 2027.

Is contention window already closing on the current core?

Admittedly, it feels strange to say this, considering the Cubs have made the playoffs each of the last two years, and one of the biggest talking points heading into the season. Of course, it helped that Pete Crow-Armstrong and Nico Hoerner signed extensions at the start of the year.

That said, considering the result of the core for the second-consecutive season, it's fair to ask if the window is already closing. It's a concerning thought, considering the money attached to Hoerner, Alex Bregman, and Dansby Swanson, but one that needs to be considered.

If there's hope, it's that the Cubs could be in a position to inject the core with new arrivals this offseason, considering the potential losses of Carson Kelly, Seiya Suzuki, and Ian Happ.

Even if the contention window isn't closing, it's become clear that their current core isn't a complete strength of the team moving forward.

What was up with the pitching injuries this season?

On one hand, injuries happen. Across the league, injuries happen. Pitching injuries have become the trend, but for the Cubs this season, it felt like there was one box that wasn't being checked when it comes to their training program for pitches.

For that reason, the Cubs need to ask the question of what, if anything, went wrong this season. Just because something is an overall trend, doesn't mean a team shouldn't look in the mirror. The Cubs need to look in the mirror and figure if the injuries were tied to something they were doing wrong, or if it was, by chance, just one of those unlucky years.

What is the vetting process for pitching additions?

Something feels off with the Cubs' vetting process for potential additions to their pitching staff. The are willing to pay a steep price for unfinished products, like the trade for Edward Cabrera, but are only willing to pay for expected results when they can find value in the money allocated.

Even then, there's a question of vetting. For example, Phil Maton was open about his knee issue throughout the offseason, and it was never right during the regular season. Yet, the Cubs felt comfortable to give him a two-year deal.

Perhaps, the answer is less gambles, and more paying for expected results at the top of the market. Sure, there's still risk involved with those moves, but the ceiling is much higher than anything the Cubs have had in recent years.

Is there too much of a reliance on run prevention?

The Cubs' model has been clear for the last several years, run prevention. Along those lines, they've had the best defense in baseball, but it feels like the last two years have proved that isn't a model that can be the primary point of emphasis for playoff success.

Not because the result is the Cubs having a bad offense, that hasn't been the case, but they've had an offense that has been flawed. The flaw is that the Cubs, outside of run prevention, they live and die with home runs. If the Cubs aren't hitting home runs at a regular clip, their offense fades into obscurity.

Valuing defense is still important, but it can't be the calling card for the Cubs.

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