Jack Schlossberg Completes Crazy Trip Around Manhattan for Charity

Jack Schlossberg, matriculating Harvard Law student and Caroline Kennedy Met Gala date (he’s also her son), recently made his way around Manhattan on a stand-up paddleboard. Why? He explains below.

With beet juice pulsing through my veins and electrolytes and Gu packs strapped to my back, I took to the East River to begin the Sea Paddle, a 25-mile circumnavigation race around Manhattan. The event itself raises money for charities involved in environmental and autism advocacy work. To fundraise, I offered friends and family a deal: Sponsor me, and I’ll write whatever you want on my shirt. I wouldn’t dare reprint their many slogans in this esteemed publication.

The race began underneath the Brooklyn Bridge, but before the whistle blew, I accidentally fell in the river trying to make some adjustments to my board. It’s true what they say: Nothing tastes quite like the East River.

I signed up for the race because I thought it sounded cool. “Paddle around Manhattan? Sweet, man! How hard could it be?” Of course, when I asked around, everyone said it was really hard and that I’d better start training.

I was whipped into shape by a group that I met through Manhattan Kayak Company, a boathouse located on 44th and 12th Avenue, which offers board storage and lessons in stand-up paddle, kayak, and canoe. I’ve lived on Manhattan my entire life, but it wasn’t until I found MKC this spring that I ever got out on the rivers that surround it.

To train for the Sea Paddle, I spent a lot of time on the Hudson trying desperately to catch up to three women half my height and weight — but I never came close. In fact, I spent the entire race on Saturday watching them get farther and farther ahead of me — this, a familiar feeling for a younger brother of two older sisters.

I can’t remember very much from the race day. The coffee, adrenaline, exhaustion, and Elvis hits blasting in my ears must have inhibited memory formation. It took me just under five hours, and I came in eighth in my division.