Secret Life of an Old-School New York Bookie

Bouncing between darkened drinking dens, one enterprising woman struggles to keep an old-time sports gambling ring alive in the age of DraftKings and FanDuel.

Illustration by Ben Clarkson

“Are you a gambling man?” Vera asks me. She hands an envelope to a bartender in the Meatpacking District as she sips on a whiskey and ginger ale. The envelope contains cash for one of her customers. Vera’s a bookie and a runner, and to be clear, Vera’s not her real name.

She's a small-time bookie, or a bookmaker, one who takes bets and makes commission off them. She books football tickets and collects them from bars, theater stagehands, workers at job sites, and sometimes building supers. Printed on the tickets that are the size of a grocery receipt are spreads for college football and NFL games. At the same time, she’s a “runner,” another slang term to describe someone who delivers cash or spread numbers to a boss. Typically bookies are men, not women, and it’s as though she’s on the chase for new blood, searching for young gamblers to enlist. The paper world of football betting has sunk in the face of the wildly popular, embattled daily fantasy sites like …