The Winner

Teddy Wayne

May 28, 2024 
The following is from Teddy Wayne's The Winner. Wayne is the author of six novels and a winner of a Whiting Writers’ Award and an NEA Creative Writing Fellowship as well as a finalist for the Young Lions Fiction Award, PEN/Bingham Prize, and Dayton Literary Peace Prize. A frequent contributor to The New Yorker and a former columnist for the New York Times, he has taught at Columbia University and Washington University in St. Louis. He lives in Brooklyn with his family.

The road beyond the white security gate, fringed by the rich green foliage of June, curved gently out of sight.

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“The code?” Conor couldn’t remember anything from John Price about a gate code. “That’s not an intercom?”

The cabdriver shook his head. “You need a code to get in,” he said. Conor tried calling John, but the connection immediately failed—just a lonely bar of finicky service. The driver’s phone wasn’t picking up a signal, either.

“Maybe you can walk,” the man suggested as his flimsy mask slipped down his nose, as it had many times throughout the ride. Conor was glad his mother was safely cocooned in their apartment back in Yonkers, where nearly everyone was still covering up in public spaces. The map on his phone wasn’t loading, so he didn’t know where exactly to find John’s house on this two-mile pinkie of land jutting from the southern shores of Massachusetts. He had to transport an overstuffed backpack, a rolling suitcase with one wonky wheel, his three-racquet tennis bag, and, most cumbersome of all, his twenty-five-pound tabletop stringing machine in another bag. Each leg of the journey he’d taken on foot since that morning—from his mother’s apartment to her Mitsubishi, the car to the Metro-North train, out of Grand Central to hail a taxi to Port Authority, boarding the bus to Providence, Rhode Island, exiting the station to this cab—had required him to shuffle along like a caterpillar.

But it was either walk or wait, with the meter running, for another car to open the gate. Conor paid, collected his bags from the trunk, and passed through an opening for pedestrians. A wooden sign nailed to a tree greeted him in cursive: 

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Private Property
No Trespassing, Please
cutters neck association

Single-lane Cutters Neck Road, bisecting and snaking down the peninsula, was quiet except for birdsong and the metallic chirr of insects. Roadside honeysuckle sweetened the tangy ocean air. To his left, a sailboat drowsed in the calm bay. The Atlantic was visible on the other side of the stiletto-shaped neck, too.

Conor had seen aerial photography of the place from real estate sites, but he hadn’t been quite prepared for the essentially unspoiled beauty of what he was now walking through—for what, incredibly, he was about to live in (on?) for the summer. He snapped a picture of the ocean to send to his mother once he had service.

He passed the first driveway, a gravel arc before a house studded with porthole windows, its slate-gray shingles blackened in spots like overripe bananas. The porch reassuringly featured a black lives matter sign; he’d had no idea what to expect politically from a gated community in deep-blue New England.

The next few houses shared the same architectural style, though there were no more adornments except for one porch flying a massive American flag that twitched in the breeze.

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Conor set down the stringing machine and rubbed his sore arm. He regretted bringing it; he might not even have any use for it over the summer. A sporting goods store in town was still restringing racquets, but he couldn’t tolerate paying for anything he could do himself.

The first sign of human life in this idyllic landscape came from a golf cart whizzing by, captained by a preteen blond girl, with two younger and even more towheaded children next to her. Conor smiled and waved in neighborly fashion, hoping they might offer him a lift on the back, but the trio only stared at him as they passed, deadpan as child actors in a horror movie.

He finally reached the mailbox for John’s address, whose number he’d fortunately remembered. Midway up the grassy driveway through a stand of trees was a short perpendicular path into more woods. There, tucked away in a clearing within sight of John’s house, hid a squat cabin, Conor’s free living quarters until Labor Day.

Or not quite free, but paid in kind. Having no luck on the job market and panicked about repaying his $144,000 in law school loans once the pandemic-triggered federal freeze was lifted, Conor had reached out in May to the Upper East Side tennis club where he’d worked summers in college. The lockdown had forced the place to close, but his old boss passed along an opportunity that had just come in: a member would put someone up in his waterfront guesthouse over the summer in exchange for lessons six days a week, and the instructor could turn a profit by charging other willing residents in the area.

And now he was here. The door was ajar; when he’d asked about getting the keys, John had told him no one locked their doors on the neck, unnerving the native New Yorker used to the nightly ritual of deadbolts and chains. Inside the one-room cabin were a twin bed and a desk, a kitchenette, and a small bathroom with a shower. John had stocked the fridge and cupboards and provided a bicycle with a basket for the twenty-minute ride to the village market.

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Few frills, but also few distractions: an ideal headquarters for hunkering down for eight-hour days of studying for the bar exam in between tennis lessons.

Conor’s phone was picking up service now, though still just one bar, and its seven-year-old battery was nearly dead. He sent the ocean picture to his mother and texted John that he’d arrived.

A few minutes later there was a knock at the door. When he opened it, a lean man in his sixties was standing a dozen feet back. He wore a dark jacket and tie paired with salmon-colored shorts and sockless loafers.

“Welcome to Cutters,” John said.

“Nice to meet you, Mr. Price.” Though they were at a safe distance, Conor fished his mask out of his pocket and strapped it on as a show of respect.

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“It’s John, please. And no need for the mask if we’re outside.” 

“Of course,” Conor said. “My mom has diabetes, so I wear a mask everywhere.”

His eyes drifted down again to John’s lower body. He’d never seen a man in pink shorts before.

John evidently noticed. “I’ve been in Zoom meetings all day, hence the Bermuda businessman look. I suppose the pandemic is the new casual Fridays.”

“I’ve been on a bus from Port Authority all day. Hence . . .” Conor gestured at his wrinkled attire.

“That Providence station isn’t much better,” John said with a chuckle. “Someone here once parked his car around there, broad daylight—stolen in fifteen minutes. Did I not recommend you take Amtrak?”

He had, but the cheapest train ticket was one hundred and nineteen dollars versus thirty-four for the bus.

“I’ve always been a bus guy,” Conor said.

John ran through the cabin’s quirks and said he’d walk over with him to the tennis court in the morning.

“Oh,” he said after taking two steps. “There’s a party on the neck tonight. Outdoors, obviously. Please consider yourself my guest for any social events here.”

“Thank you very much,” Conor said. “I’m pretty beat, so I’ll probably stay in.”

“You sure? I know standing around with a bunch of stiff Wasps may not be the most exciting night, but you might meet some new clients. Assuming you don’t mind mixing business and pleasure.”

Conor had only three tennis lessons lined up in addition to John’s unpaid sessions. Even if all of them turned into weekly appointments, he’d need to make much more money this summer.

“As long as the Wasps don’t sting,” he said.

After a harrowing couple of seconds in which Conor worried he’d offended him with his bad joke, John smiled.

“If we do, we’re numb to it ourselves,” he said. “God’s frozen people.”


From The Winner by Teddy Wayne. Copyright © 2024 by Chico and Chico Inc. To be published on May 28th 2024, by Harper, an imprint of HarperCollins Publishers. Excerpted by permission

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