Each month Gary Wilensky writes “Seven hundred and fifty and no/100 dollars” on a check printed with a picture of a log cabin in the mountains—rent money for his Manhattan studio apartment.
There are twenty-nine floors below him and five above him. In the seventies, Donnie Brasco took up residence in the building during his undercover infiltration of the New York mafia. In the eighties, two men tied together by a bedsheet passed Gary’s window on the way down.
The windows in his apartment face east in the direction of the river. He has a galley kitchen, hardwood floors, and an alcove that separates the sitting area from the sleeping area. In less than a year, officers will raid his home, climbing over stacks of vintage tennis magazines, to haul out evidence: boxes of VHS tapes—including homemade videos starring Gary Wilensky in compromising positions—and a stack of books—Peterson’s Summer Opportunities for Kids and Teenagers; November of the Soul: The Enigma of Suicide; The Joy of Sexual Fantasy. For now, however, he isn’t known to have visitors.
The Ruppert Yorkville Towers is composed of four buildings that stretch between East Ninetieth and East Ninety-Second Street on Third Avenue and up into the sky. The redbrick towers were erected in 1975 as part of a city housing plan to provide moderate- and middle-income residents, who would otherwise be forced out of the neighborhood by rising costs, an affordable place to live.
Just two blocks west of the towers is Park Avenue, with its scrubbed prewar apartments. Beyond that is Madison Avenue, home to three girls-only private schools, and the Daughter’s public school. Past that is Fifth Avenue, the museums, Central Park—an urban garden maze that divides the East and West Sides of Manhattan—and some of the wealthiest homeowners in New York.
To the east of Gary’s building, within walking distance, is the mayor’s house, the East River, and two more girls’ schools—one where he teaches, the other where he picks up one of his students in his junior program. (“Pippa,” he mistakenly scribbles on the invoice.)
For Gary, the apartment is a deal; for others in the neighborhood, the building is the dividing line between the “good” neighborhood and the “bad” one. When you’re rich, the less fortunate are what frightens you the most. But Gary is used to living modestly under the shadow of other people’s fortunes. As a teenager in the Long Island hamlet of Roslyn, not far from the Gold Coast mansions that inspired Fitzgerald’s Gatsby, he lived in a small apartment complex with his father, a divorced garment manufacturer. The town wasn’t then as wealthy as it would become, but the Victorian homes were still more elegant and fuller than where he lived.
There are things you can’t control and others you can.
A basketball, for instance. It didn’t matter that Gary was five-eight his junior year, he still brought the varsity team to victory. And tennis. Ping-Pong, even. Give Gary Wilensky a ball and he’ll never give it back. He became his own man on the courts.
Gary’s grades were low compared to those of his Ivy League–bound friends, but he wasn’t working toward his future; he was living it. He was older than the kids in his class, and dressed the part—snappy ties, tailored pants jangling with car keys. Gary had wheels before any of his friends, zipping through town on double dates. And those who doubted his maturity might have second thoughts when they saw him on the dance floor.
He knew all the steps and wasn’t flustered by the nearness of a young woman’s body, wasn’t afraid to pull her close to his chest, to rock her back and forth, to suspend her at an angle above the floor so that she couldn’t catch herself should he choose to let her go.
He was different from the other Jewish boys in Roslyn, who were all bound for top-floor jobs in Manhattan. For Gary, opportunities were closer to the ground.
He started as an instructor at Midtown Tennis on Eighth Avenue. The courts were narrow and space was tight, but in the late sixties and early seventies, it was just about the only game in town. On any given day, there was Kurt Vonnegut Jr. trading shots with Mike Wallace, or Morley Safer in the locker room.
One regular, an ad executive who moonlighted doing PR for Catskills resorts, scouted Gary to run tennis programs at two of his hotels: Grossinger’s and the Concord, a couple of hours north of the city. The Catskills were still elite summer destinations in the seventies. Elizabeth Taylor and Richard Burton made the rounds, and once Bill Cosby flew in for a doubles match. If the Borscht Belt comedy scene was dwindling, the showmanship remained. The resorts advertised former pro-circuit players as instructors, flew in marquee champions for matches, and built A-frame roofs over their courts for twenty-four-hour all-weather play. Soon Gary started having ideas of his own: tennis as a party, a show, a brand.
Back in the city, Gary became Midtown’s tennis director, hosting leagues and late-night tennis mixers with the kind of clientele who were connected to the press, who knew so-and-so at this newspaper or that magazine.
If he had a pet project, it wasn’t long before he was talking it up in the papers.
The Times covered his singles mixers and the short-lived tennis shop he opened on Lexington Avenue, which sold collectors’ items and gear for pros. Newsday did a write-up on his tennis-tip hotline. But in 1979, while he was director of the Central Park tennis courts, he received national attention for his signature gimmick: tying on a pair of roller skates and challenging sneaker-wearing players to a match for sixteen dollars a pop. People magazine’s headline read, “The big wheels in tennis are Borg, McEnroe and Connors. Now meet Little Wheel Gary Wilensky,” and featured a half-page photograph of Gary standing at the net in tennis shorts and roller skates. Though the first line of the article must have burned a little. “An aging tennis pro has got to hustle . . .” At the time, he was forty-one and his business was just beginning to take off.
By the next decade, Gary was selected, along with a handful of other coaches around the country, as a United States Tennis Association Master Professional—a title he’d later tack to the résumés on the back of his invoices.
Prince, the athletic company, had hired him to promote and coach customers who purchased their special edition $1,000 rackets. “For the very serious player, that’s not really so much,” he told a UPI reporter.
By then he’d given up working for clubs as a tennis director—there was more money to be made renting out courts as an independent instructor. Though his dismissal from Midtown—where, according to one staffer, Gary tried turning fellow pros against his boss in order to take her job—likely contributed to the decision.
Between referrals from his adult students—some of whom enrolled their children in his junior program—and the growing roster of Manhattan girls he’d recruited working at camps up north, his client list grew.
By 1992, Gary Wilensky had narrowed his focus to younger players, firmly affixing himself as an Upper East Side institution. Now he does well for himself, pulling in a solid six figures. And occasionally he gives back, teaching underprivileged kids about the basics of tennis—a move that served him when he was called before a judge, four years back.
Still, he lives modestly. Ramshackle car. Rent-controlled apartment. Low overhead, minimal expenses, no family to support.
He spends his money like an adolescent with a new allowance—collecting vintage tennis memorabilia and costumes and ordering takeout food. Mostly he splurges on his students—doling out gag gifts, movie tickets, candy, and pizza dinners. Over time, his students have come to expect this. He’s their Santa Claus, their Grandpa Gary. That’s what the girls call him, though he’s only fifty-six.
Fuddruckers, a chain of family-friendly burger joints, opened an outpost on the ground floor of his building. Planted out front is a yellow-and-blue mushroom, tall as any ten-year-old. It might as well be a dog whistle for kids. Gary hears it. Every now and then, he takes one or two students there for burgers and shakes. Afterward, he’ll drop them off at home and drive back along Third Avenue—the night lit by a patchwork of storefronts still glowing from the inside.
At home, he peels back sticky labels printed with his phone number and the promise of a “new tip every day!”
Gary launched his tennis-tip hotline years ago, and it’s still going strong. He records a new message on his answering machine every day. Usually he welcomes callers and offers pointers on the game, sprinkling his message with some patented Gary humor.
“Rhythm is very, very important,” he once said in a recording on his hotline. “In tennis you have to synchronize the toss and the backswing. You must get the body to relax . . . Gynecologists may disagree, but rhythm works.”
When his hotline was first covered in the papers—the New York Times, Newsday—he was mostly coaching adults and noodling around with new ways to drum up business. That was almost fifteen years ago. Now his target audience is kids.
When he presses his number onto index cards addressed to his students—Park Avenue, East Seventy-Second, East Eighty-First—he might think of the scrubbed prewar brickwork on their buildings and the glass doors that open for them when they run from his car, tennis rackets bumping at their sides.
He might picture the rest of what they call home: the clean, elegant foyers lit softly by Tiffany lamps leading to long oval dining tables blooming with centerpieces; the bedrooms with tucked-in sheets, ironed and folded underneath two propped pillows, crisply encased in white linen, waiting for hands, heads, and cheeks to press them down. And maybe on a desk beside the bed or pushpinned to a bulletin board overhead is the index card with his number on it. The phone, a portal from their home to his.
He stacks the index cards before dropping them in a mailbox.
In the morning, the Third Avenue bus rolls up outside his apartment building, releasing a gigantic sigh when its doors open. This is not the flashing, screeching, pummeling underground subway system that speeds from borough to borough, but a kinder, gentler MTA for the very old and the adolescents who have graduated from school bus to soft public transit.
Block letters request passengers reserve the seats closest to the driver for the elderly or the disabled.
Starting at seven a.m., students in kilts and blazers crowd into the M98. The bus crawls up Third Avenue, stopping along the Upper East Side where the private schools are clustered. Dalton, Nightingale-Bamford, Spence, Brearley.
They load inside, pushing each other’s JanSports, flashing soft pink bus passes, hunchbacked from their textbooks, shuffle-stepping to the seats in the back, as far away from the adults as possible.
Somewhere among them is Gary Wilensky, perhaps slouched in one of the backseats, or gripping a silver bar overhead, scanning the new arrivals as they collect around him.
By the time the bus reaches Ninetieth Street near Gary’s building, most of the kids have cleared out. An empty Snapple bottle might roll around on the rubber floor, or a hardened pink splotch of Bubblicious might stick to the edge of a blue seat. And beside it, a candy-colored strip of paper no bigger than an index finger, printed with a phone number. No name, no explanation, just seven numbers in a row—prank-call bait for anybody of a certain age with a certain sensibility.
He has written his number on colored paper and cut it into strips. They are scattered onto seats, waiting to be discovered. A clue in a scavenger hunt. The case of the mysterious phone number.
When he is gone, multiple bus riders will report finding these colored strips of paper, which trace back to Gary Wilensky’s home phone. By then we will only assume what his intentions were. We will only imagine him lying in bed when the answering machine picks up, listening to the feathery sounds of their breathing.