Why I Hate the Playoffs

A season proves who you are. The playoffs decide what you are remembered for.

Baseball is an organizational game. You build depth. You manage fatigue. You celebrate converting 81–81 seasons into 90–72 seasons and then 92–70. You believe that over enough time quality shows. In that realm I feel at home.

Yet when the calendar flips to October everything changes.

It becomes a game of snap judgments, high leverage, and momentum. A cold bat, an ill-timed error, or a bullpen meltdown can erase everything that was built over six months. One hundred sixty-two games of structure and planning do not guarantee anything when the rules of the season are rewritten.

That is where my brain rebels. In business I plan long. I track trends, not isolated days. I expect my strategy to carry me through adversity. So why should the culmination of a baseball season be decided in such a narrow fashion.

Because that is the beauty and the brutality of the playoffs.

The Brewers are this year’s proof of concept. Their regular season dominance argues they deserve October validation. The only guarantee in October is uncertainty. Will their depth matter more than hot streaks. Will role players step up or wilt. Will composure beat fire.

I think back to Seattle in 2001. They won 116 games, tying a record. They dominated across months, across metrics, across everything. Yet their season is remembered by the games they did not win. In five October games they lost the ALCS to the Yankees and went home. All that structure and excellence undone by small swings. That for me is the heartbreak of the postseason.

And yet even knowing the odds I cannot look away. Because in those moments character shines brightest. The pressure reveals truth. The players who hold steady when everything is magnified show us something we can carry beyond the game.

So yes, I hate the playoffs. I hate that they distort the narrative. I hate that so many brilliant seasons end in what feels like randomness. And yet that is also why they fascinate me. Nothing else in baseball or in business comes with that kind of pressure.

This October I am pulling for the Brewers. They deserve it. But I am rooting for my Dodgers. Either way I will be watching every pitch, every swing, and every moment. Heartbreak or glory.