When dollar bills flutter from a boat deck in Chicago’s Playpen, they’ll float for a while before they sink, Captain Enoch Morgan tells me as a group of women twerk nearby to “Looking for the Hoes (Ain’t My Fault),” by Sexyy Red, singles tucked into their bikini tops.
“We had somebody do a scuba dive because somebody had lost their phone,” Morgan says. “Didn’t find their phone, but they found a drone, a $20 bill, and a pair of Gucci sunglasses.”
Morgan held a small plastic cigarette holder between his teeth as he watched over the birthday party unfolding in the Playpen, the no-wake party zone abutting Chicago’s historic Gold Coast and nouveau riche Streeterville neighborhoods, where flotillas can stretch as far as 50 boats long.
The floating, daytime club has become synonymous with debauchery and danger. Multiple partygoers have gone missing. Boating mishaps have resulted in severed limbs. This summer, a Chicago alderwoman proposed a life-jacket law after a woman drowned in the Playpen in June.
Lacking access to a vessel of my own, I borrowed an inflatable kayak at the last minute from a former Franciscan priest. Accompanied by my co-captain, Graham, I paddled out from Ohio Street Beach to see whether the Playpen lived up—or, more accurately, down—to its reputation.
Although the Coast Guard polices the Playpen, there seems to be little consensus among boaters around which force has jurisdiction. As a Chicago Police Department boat drove by, revelers openly smoked marijuana.
“There’s no rules. It’s like the Wild, Wild West out here,” says Edith Bayran, who lounged at the end of a sleek, 63-foot yacht. Bayran and her husband started with a more modest, 38-foot boat before slowly working their way up to their latest craft.
A native Chicagoan, she complains that new, inexperienced boaters have changed the Playpen. Professional captains echo that sentiment, noting the growing, poorly regulated market in slipshod boats for hire.
As the owner of a water-taxi service, Liam Poczatek ferries passengers to their boats. But on some weekends in the Playpen, his water taxi often converts into an emergency service. He says the Playpen’s transformation began about four years ago, when a rise in charter services shifted the bay from a family-oriented boating spot for private vessels to a more commercial, reckless environment.
“They’re trying to run illegal charters and things of that nature, without necessarily having the skill set that will align with that,” says Poczatek, who saw a charter boat run into the concrete wall bordering Lake Shore Drive this past weekend.
Throughout the day, I heard Playpen veterans describe these careless operators as “a few bad apples” amid an otherwise lively, even wholesome atmosphere. Meet Teddy Piekut. A local legend, Piekut rises high above the boats every weekend in a water-propelled jet pack. A proud Polish immigrant, he flew a half-Polish, half-American flag and tied up to another yacht, waving a Ukrainian flag.
Sitting on the deck, Piekut’s friend Daniel Golonka rolled his eyes at the next flotilla just beyond them, where one boat was decorated with a pair of enormous flags, one with the revolutionary “Join, or Die” snake, and another with the text of the Second Amendment.
Piekut glided through the air like the Green Goblin. He dove into the water with ease, then grabbed his girlfriend from the yacht’s deck. The pair waltzed gracefully in front of the Chicago skyline.
“You have to try it,” his friends said.
Ignoring my fears of a lost arm or leg, I strapped on a life jacket and braced for Piekut’s arms. Suddenly I felt my feet leave the deck, and my toes searched for a spot on the board. As we spun around in the air, I thought at any moment I would end up like a pair of Gucci sunglasses, stuck at the bottom of Lake Michigan.
I would like to report that my view from above the Playpen gave me the fullest picture of the party scene, but I closed my eyes nearly the entire time. I landed back on the boat and collapsed on top of a cooler.
“Have a drink,” somebody says, not for the first time that day.
Leigh Giangreco is a Chicago-based freelance journalist. Her work has appeared in The Guardian, The Washington Post, and Politico magazine
