“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 FanDuel or DraftKings.

“Business is down because of FanDuel, DraftKings,” Vera says. “Guy bet $32 and won two million. That’s a load of shit. I want to meet him.” There’s a nostalgic feel to circling the numbers of a football spread. The tickets have what look like traces of rust on the edges. The college season has ended, and she didn’t do that bad this year, Vera says. What’s left, though, are pool bets for the Super Bowl.

Vera began running numbers back when she was fourteen years old at a snack bar where she worked as a waitress. The chef called in on a phone in the hallway and she’d deliver his bets to bookies for horse races. It leant an allure of youthful defiance. The same was true when she first bartended in the ’80s. “Jimmy said at the beginning, ‘I’m going to use you. Just so you know,’” she says, remembering a deceased boss. “‘You go into the bar, bullshit with the boys. You can talk football with a guy, you can pull them in, and then they’re yours.’” Jimmy died of a brain hemorrhage. Her second boss died of brain cancer. Vera says she beat breast cancer herself, even though she still smokes. She underwent radioactive treatment and refused chemo.

Dead bosses left behind clients to run and she’d oversee them. Other runners despised her at first. They couldn’t understand why she’d have more clientele than them. “And they’d say, ‘who the fuck is this donkey, coming over here taking my job?’” she says like the men are throwing their dead weight around. Sometimes the other runners duped her, for instance a runner we’ll call “Tommy” kept winnings he was supposed to hand off to her for himself. “Tommy liked to put coke up his nose, and play cards, and he liked the women in Atlantic City. He’d go and give Sam $7,000 and fuck off with the other $3,000. He tells the boss, ‘Go tell the broad.’ And I says, ‘Fuck you. It’s like I’m just a fucking broad to you. I don’t count.’” It’s of course forbidden for a runner to spend cash or winnings meant for customers on personal vices. But fellow runners and gambling policemen trust her. She never speaks bad about them, their figures, winnings, or names. She never whines if she doesn’t make commission.

She says she can “keep her mouth shut” which is why she’s be a runner for nearly 25 years.

When she pays customers, she exchanges in person, never secretly leaving envelopes of cash behind toilets or under sinks in tavern bathrooms. Over the years, though, she’s lost up to $25,000 from men not paying their losses. “There’s a lot of losers out there,” she said, “just brazen.” For the football tickets, she funds her own “bank” that’s self-generated, almost informally, by building her worth on the success of the college season’s first few weeks of bets in the fall.

“I ain’t giving you no figures,” Vera says and drinks from her black straw. Ice cubes turn the whiskey to a lighter tan. She reaches for her cigarettes and zips her coat. She questions the recent alterations in the spread for this weekend’s Super Bowl between the Carolina Panthers and the Denver Broncos and squints at her drink and pays the bartender. Her movements lumber, as her thoughts do. The favorability of the Panthers has shifted from three to four-and-a-half to five quickly in the past week. She wants the Panthers to win by six or seven in order for her bet to be a success, and predicts Cam Newton will lead them to a double-digit win over Peyton Manning.

Outside, she lights a cigarette before moving to a new bar. Someone she didn’t want to see had sat down in the first one. She says there’s a man there who tends to harass her. She continues further north.

At the second bar, a poster tacked to the wall beyond the counter shows a 100-square Super Bowl grid or “boxes.” “Are you running any Super Bowls?” Vera asks.

To win a Super Bowl box, at the end of each quarter, the last digit of either of the teams’ scores need to match the number of your selected box in the grid. The bartender hands Vera the grid. The bar lights brighten. Vera traces her finger across its outline, explaining that if the score is Broncos, 24, and Panthers, 27, by the third quarter, that’s row 4 and column 7. Prize money varies each quarter, and the pool only works properly if bar patrons buy out all the squares.

Vera recalls a pool in 1990, the Giants-Buffalo Super Bowl XXV. Buffalo lost 19 to 20 after missing a field goal from 47 yards. All the Bills knelt and prayed for that field goal. “Cops in the 20th Precinct won. It was 0 and 9,” she says, describing the box numbers that matched 0 and 9. But her deceased boss squandered the $50,000 pool over the course of the year, spending it on rent, gas and cigarettes. Bettors had paid installments throughout the year for $500 boxes.

Nobody got paid. There was a “contract on his life.”

The bartender stows a white envelope of cash before pouring an apricot-honey mix for Jell-O shots. Vera rolls up a napkin and spins it in a beer that looks flat to give it foam.

“For the first bookie I worked for, my name was ‘Ice,’ long before Ice-T,” she says, holding out her hand, rubbing where the ring with her codename would fit. “He got me a ring, which I lost. Twenty-one diamonds, made ‘ICE.’” The bookie told her he had it inscribed ICE because she was “a cold-hearted bitch.”

* * *

James K. Williamson is originally from South Carolina and a master’s candidate at Columbia University Journalism School. To read more of his work, visit www.jameskwilliamson.com.

Ben Clarkson is an illustrator and filmmaker who lives in Montreal. Follow him on Twitter @benclarkson.