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Midnight Madness

“Midnight is coming.”

So began the rather ominous-sounding subject line of our first email from Game Control. This is what kicked-off the final week of preparation, anticipation, excitement and frenzy leading up to a once-a-year event called Midnight Madness, that stormed New York City this year on October 5th. On that cool autumn evening, 30 teams of 10 people each, drawn from every level of several well-known banks and hedge funds, were let loose on an epic brainteaser/scavenger hunt that raised $2.9 million for Good Shepherd Services, traversed the city and unfolded over the course of more than 16 hours through the night. We were united by the Type A competitive over-drive you might expect of such professionals, but also by a tremendous geek-love of puzzles and brainteasers commingled with a desire to see new parts of New York City in an entirely different light…or perhaps more accurately I should say, through the night hours devoid of light, and into the dawn.

Did we know what to expect? Not really. I think all of us were taken by surprise at the level of complexity and devilish, esoteric specificity of the puzzles bestowed upon us. The first puzzle was a 3×7 grid wherein we were required to match a tiny snapshot of a movie scene to the proper type of film as well as the correct narrative arc. Identifying each movie (ranging from well-known “Forrest Gump” to virtually-impossible “Suspiria”) was the first step, but placing each in the precise, correct spot of 21 possible spots confounded us for several hours. A series of bizarre images posted on the wall of an underpass in midtown upon close examination would each translate into a color of an NYC subway line and the names of two stops. By counting how many stops during regular hours existed between those two points, you would derive a number, and thus derive a corresponding letter, and thus build the right words in total.

As the hour approached midnight, on Pier 25 strange metal boxes that we had received at the start line emitted musical notes that had to be played to mimic the sounds coming from a boat lingering offshore. Pier 25 is in Tribeca, nearly directly across the street from the office where I have worked for over 10 years, and that was the first time I had ever walked (or in this case, ran) down its length, marveling at all that I saw. Another diabolical puzzle anagram brought us to the “Bloody Angle,” a bend in the middle of tiny Doyers Street in the heart of Chinatown. In 1994 the New York Times said this was the site of more violent deaths than any other intersection in the United States.  Standing there in a literal bend in the road, it was strange and eerie to imagine so much bloodshed along this tiny, ordinary-seeming road and to imagine the weight of that kind of history contrasted to the current day.

Between the approximate hours of 3:30 to 5:00 am, sitting out on the sidewalk on Park Avenue, we pondered a complex puzzle masquerading as a cocktail and beer menu…as others who had clearly been partaking of actual drink menus hobbled, stumbled, and wove their way past us in search of taxis, homes or hotel rooms. My teammates and I would look up occasionally, shake our heads, smile and say, “God, I love New York!” It was just a regular Saturday night here in the city—we were the components that were out of place, not them—and then we’d return our gaze to the puzzle and play on. On the whole, New Yorkers mostly took our presence in stride. Some were curious, others intrusive, but overall the city absorbed our freneticism with its usual aplomb.

As the night and day wore on, a safe was cracked, doors were opened, a cemetery was explored, mannequins and M&Ms were pondered, hints and clues were traded and teams split up and reconvened together countless times in order to explore Chinatown, the East Village, the West Village, Fifth Avenue, the Lower East Side and many other NYC neighborhoods before finally crossing the finish line at 7 World Trade Center—a fitting end to a uniquely New York event. After all was said and done, and we’d returned to our desks and everyday existences, we all went through an odd bit of withdrawal. My team has already reconnected twice in just the few weeks since the Madness officially ended, to reminisce (or commiserate) about how impossible most of the puzzles were, cheer each other on again for cracking some of them, and most importantly, to start strategizing even now about how we will approach the game next year.

Because after all, midnight is coming…

Amy found her way to NYC over a decade ago and fell irrevocably in love with the city.  She admits to now being stricken with a full-blown case of Midnight Madness as well.  

For more details:

For the official story, photos and more insight into each puzzle: Midnight Madness 

NY Times



Midnight is coming.

Destination Details