Nico Deportago-Cabrera first took up cycling around Chicago in 2004 after losing his driver’s license. Four years later, when the band he played in broke up, Deportago-Cabrera started working as a bike messenger and began racing alleycats against fellow couriers. Riders would speed from checkpoint to checkpoint across the city in unsanctioned races, completing various tasks along the route.
Deportago-Cabrera won the North American Cycle Courier Championships in Boston in 2009, and again in Brooklyn in 2016. He signed on as a Red Bull-sponsored athlete, and has competed in the Cycle Messenger World Championships. His racing seasons each year now pivot from messenger-style races to cyclocross, gravel events, and ultra-endurance. September’s Bay Climb race was a short sprint straight up De Haro Street in San Francisco, with gradients exceeding 23 percent—very different to his flat hometown.
He still lives and works in Chicago as a bike messenger. Over the last decade he has seen the courier industry forced almost out of existence, and then evolve and flourish as the app-driven gig economy has grown.