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Michael Jordan at the 1988 Slam Dunk Contest at Chicago stadium

Sometimes It’s Better Before It Gets Good

The Madhouse on Madison, Then and Now

When I was growing up the original stadium where the Bulls played wasn’t the posh, corporate United Center. It was Chicago Stadium. Though they could barely afford it, in December of 1990 my parents got me the best Christmas gift I have ever received. My Dad and I went. Jordan scored 42. Pippen 34. Bill Cartwright was the player of the game. When they introduced MJ it was the loudest thing I have heard, at any arena, ever. It still is to this day. It was only then that I properly understood why they called that place The Madhouse on Madison.

When we opened up at 488 Madison this week, at 52nd & Madison, my brain went laterally back to that day. On the way to the game, my dad freaked me out by telling me how dangerous the neighborhood on the pre-gentrified city’s West Side would be. It was only a few blocks off the Eisenhower, but 11 year old me was terrified as we approached. After the Bulls victory we emerged into the icy, bitter Chicago cold. A street vendor shouted “get your Pistons suck t-shirts”. We walked quickly. Though we had beaten the Warriors that night, getting past Detroit was the entire city’s focus. It’s funny how the mind works, that this week I would find in a recessed drawer of my memory what a street vendor said 26 years ago. It’s even funnier how life works. Madison is our 26th guideshop.

I still don’t know how the captain of his high school scholastic bowl team became the most unlikely fashion CEO of all time. Or how a decidedly un-”cool” kid built a “cool e-tailer.” All I know is if I could go back to that brutally cold night in Chicago and do it all again, I would. Little did my dad and I know then, as we drove home, that the Bulls would go on to beat the Pistons and win six championships. When we finally vanquished Detroit, they wouldn’t even shake our hands. From there, the six titles. It’s only in retrospect that you realize: sometimes it’s better before it gets good.

Spirit animal @bonobos, swan hunter @redswan, brother @monicaandandy. I love cilantro but love even more the people that hate it

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