James' World 2

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First you hear the collars, like a chorus of bells softly ringing. Then, the patter of paws. You look up and see a mirage of floppy ears, wagging tails, and fur—it’s a pack of dogs approaching, shepherded by their seemingly fearless leader: the dog walker.

On any given day in New York City, there are countless dog walkers out and about, tending to some of the city’s estimated 600,000 dogs. And aside from caring for the beloved pets of New York while their owners are at the office or otherwise occupied, many dog walkers are a fixture of their neighborhoods—bringing a daily jolt of joy to kids at the bus stop, holding the door for postal workers, generally keeping an eye on things. They know the rhythm of the city, and they help keep things in tune.

For some, dog walking is a part-time job; for others, it’s a trade and a passion. For many New Yorkers, it’s a way to make ends meet so they can pursue creative interests as artists, performers, and writers. No matter their backgrounds, though, every good dog walker has one thing in common: a love of animals. They care about them, and connect with them. They’re able to divine things from the dogs, based on a tug of the leash or the tiniest twitch: Riley’s riled up; Cookie wants to fight; Lou needs to pee.

Costello Caldwell, 78

Costello Caldwell has been walking dogs on the Upper West Side since the early 1980s.

He grew up next door to a boarding kennel in Maryland, where he worked after school and during the summer, and quickly fell in love with dogs. When he moved to New York, he worked in fashion, retail, and restaurants until he got sick with pneumonia. As he recovered, he would sit in the park and see dog walkers who seemed happy. One day, he had an idea.

“I bought uniforms for five of my friends, dressed us all the same way, borrowed all the dogs in the neighborhood that I knew, and we took a walk down Amsterdam and Columbus Avenue. I called it ‘goin’ fishing,’” he says with a laugh. He had business cards with his business name—Royal Wolves Academy—made, and he styled not only the people but the dogs, too, with special leashes.

“This is New York City, and they love a drama. They see five people walking down the street with a bunch of dogs all dressed the same way, they will stop their conversation and pay attention.” It worked. By the end of the day, he had his first seven clients. “That’s how it all began.”

Caldwell, 78, who is an artist and has made headlines for his eye-catching style, lives in the neighborhood. He walks dogs in Riverside Park, seeing the same people every day. “They call me the mayor of this area,” he says.

“Clothing is part of my art,” he says, describing his look as an eclectic mix, like Indiana Jones meets the Marlboro Man, meets Peaky Blinders. “It’s easy for me to love walking dogs because I put fashion into it. I give them leather collars and leather leashes, and I write their names on everything. I make diaries for the owners to look at in leather-bound agendas. I burn their names into the leather. So to me, all of this is art.”

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“They call me the mayor of this area,” says Costello Caldwell, a dog walker on the Upper West Side known for his eclectic style. Photographed by Peter Fisher

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