Zach Schonbrun ‘05

Adam Nagler’s paddleboard expedition from Virginia to Nantucket, Massachusetts, in 2021 was a natural evolution of years of commitment—and demanded grit and determination. Paddling 724 miles for 34 days on the water required the constant balancing of board and body with every ocean variable, including tropical storms. Nagler’s expedition helped raise funds for a Nantucket community-based mental-health clinic and addiction treatment center.


Photos provided by Adam Nagler except where noted.

Less than two days into the most daring endeavor of his life, Adam Nagler '85 knew he needed to "improvise, adapt, and overcome" like never before. Hurricane Elsa was on his track four days to the south and Nagler was a good three days from the nearest navigable inlet, hauling a 300-pound sled across 160 square miles of shoals.

Nagler's launch from Kiptopeke, Virginia, at the mouth of the Chesapeake, with the sled he had to ditch due to an approaching tropical system.

Nagler's launch from Kiptopeke, Virginia, at the mouth of the Chesapeake, with the sled he had to ditch due to an approaching tropical system.


He had provisioned 28 gallons of water, 50 pounds of endurance "fuel," 20 pounds of medical supplies, and almost as much safety and backup equipment as a Coast Guard patrol boat. Now, with Elsa coming, he was going to have to ditch the sled. Nagler gave himself one hour to triage a year's planning.

Already things had gotten off to a rocky start. His expedition, named "Deep Fog Direct," was originally charted to go from Cape Hatteras, North Carolina, to Nantucket, Massachusetts, following a line to the west of the canyons of the continental shelf—two weeks out of sight of land, across hundreds of miles of open ocean. Alone and standing. On a paddleboard.

But a series of unpredictable early-season tropical systems off Cape Hatteras during the first weeks of the expedition "weather window" made such a route implausible. A fool's errand, Nagler thought. Better to launch from the mouth of the Chesapeake and stick nearer the coast.

A safer trip, but hardly easier. Two pitch black, moonless nights in, he set the sea anchor so he could get some rest. An hour later, hundreds of yards outside the breaker line, a rogue 8-footer tossed him like a piece of flotsam. All his gear was tied down, so he didn't lose anything; but underwater, in the dark, wearing a 25-pound pack, Nagler had to disconnect and jettison the anchor. A parachute with 40 feet of line wrapped around the upside-down 150-pound board and Nagler himself, in breaking waves, in a blacked-out sea, may not have been survivable. Two hours later, having navigated 3 miles of shoals to a barrier island, he came ashore, hard, on an oyster bed, slicing both his feet. The infection set in almost immediately. Within a day his feet and legs below the knee blew up to the size of small honeybaked hams. It would take three more days of paddling plus a day before he received treatment beyond his rather useless topical salve.

He took refuge with a "godsend" who brought him to a hospital in Lewes, Delaware, where he received intravenous antibiotics for cellulitis, while the storm raged outside. By the time he was released late the following afternoon, all that was left of Elsa was an angry sky. At sunrise the next morning, he set out from Cape Henlopen. It was 21 miles across the mouth of Delaware Bay. "Deep Fog" was about to live up to its name. There are many ways to get to the island of Nantucket. Arriving by standup paddleboard, a "stock" 14-footer fully laden, is arguably the hardest conceivable.

For Nagler, 54, it's another notch in a Herculean quest to remake his life—physically and mentally—that began on New Year's Day in 2014. He had gone as hard as he could in the ocean and mountains through his late 20s, until the "desk" took over for too many years. Then, a rare heart infection at 42 led to open heart surgery. As his past life receded, he became resigned to his reality and eventually embittered.

"I'd gotten fat and angry and mean," Nagler says. "I looked at myself in the mirror and said, 'If I don't do something about this, I'm going to die young.'"

He dreamed up the "This is 50 Sufferfest Tour"—a unique series of solo and self-supported, self-inflicted, brutally challenging "epics"—to prove to himself that he could far outdo anything he had accomplished in his "prime"...to take care of "unfinished business." Some might call it a midlife crisis. But the efforts evolved into an ethos, with 15 principles for "building your path," as he calls it.

Overhead view of Nagler from drone footage outside Moriches Inlet, Westhampton Dunes, New York. BILLY MACK

"I need to maximize my potential," Nagler says. "When I set out on these expeditions I take a 'blood oath' with myself that I cannot be broken, that I'll do whatever it takes to see the mission through to its end."

Along the way to becoming a world-class ultra-endurance athlete, he never set his sights on any organized event. Nagler instead focused on pushing his limits in ways rarely tested.

"Originality is important to me," Nagler says. "I'm not interested in the FKT—Fastest Known Time—on a well-worn course. I'm about the OKT—Only Known Time—on a course that makes no sense at all."

In July 2017, he set out to quantify his fitness and mindset with two "test pieces." The first, a 140-mile standup paddle from the Brooklyn Bridge to Montauk Point, at the tip of Long Island, which he completed in 74 hours (a time he has since improved to under 55 hours).

Three months later, he in-line skated 122 miles of the Pacific Coast Highway from the Pier in his hometown of Santa Barbara, California, to Malibu and back—in 18 hours and 45 minutes—on one of the hottest, windiest days of the year. The 5,300 feet of combined elevation gain and loss—on skates—was positively frightening. Nagler was only getting started.

He lost 14 pounds and three toenails during the first epic in April 2018, while beach and trail running, mountain biking, in-line skating, and standup paddling 1,000 miles around Santa Barbara for 10 days straight.

Outside Shinnecock Inlet, Southampton, New York. NORM STUMP

Outside Shinnecock Inlet, Southampton, New York. NORM STUMP

Six short weeks later, after running 128 miles from Manhattan to Montauk and then cycling three times that distance, both direct, he reached Nantucket via standup paddleboard for the first time during the second epic—having set off from Manhattan, a distance of 247 miles. After a few days of rest, he paddled 178 miles back to the east end of Long Island.

The expedition he was embarking on now—a natural evolution of years of commitment— would be complex for reasons Nagler had anticipated and some he could not foresee.

Twenty-five miles northeast of Manasquan Inlet, New Jersey, Nagler met a lone boat chumming and fishing for sharks.

But it wasn't the chum slick that concerned Nagler. It was the 15 to 18 knots of wind and 4- to 6-foot seas driving him off his line to Long Island. It would take him 25 hours to complete this leg of the journey: the open expanse east of the tip of New Jersey's elbow forming the main shipping lanes into New York Harbor. The length was equivalent to three laps of the English Channel. He was one lap in, and his right hip began to throb.

Part of what Nagler relishes about the challenge of paddleboarding for long stretches is that it is so often deeply uncomfortable, the constant balancing of board and body with every ocean variable. Simply remaining upright can be an arduous task. Remaining on course when the wind and swell are not with you for hundreds of hours requires uncommon grit and determination.

Out there, in the thick of it, Nagler's body finally said what his mind refused: "Enough." The piriformis muscle on his right side—a muscle deep beneath the glute—"just exploded," Nagler says. "I collapsed. I'm in shock, about to pass out. I'm lying in the water screaming."

On the satellite GPS unit he uses to communicate by text with his on-land safety manager, Kyle Collins, there is a toggle that will deliver an SOS signal to Garmin's International Emergency Response Coordination Center; triggering a search and rescue operation. For the first time, after 10,000 hours and 55,000 miles of training and expeditions, Nagler says, he almost pushed it. "It was close, really close." But as he likes to tell Collins (who winces at the thought), "I've gotta be pretty much dead to push that thing: bleeding out, direct lightning strike, run over by a ship...that kind of stuff."

"I knew first I had to get a wetsuit and hood on," Nagler says. "It was cold enough I was going to be hypothermic in a couple hours regardless, because physically I couldn't get into anything other than a 'shorty.'"

Though barely able to bend his leg, Nagler gritted through the morphine-worthy pain, and found a little bit of support in that area, the compression, helped after the suit was on.

Somewhat. Enough.

"I'm going to make it," Nagler told himself.

He paddled for 17 more hours until he reached the beach a couple miles east of Fire Island Inlet at first light. Even in a delirious state and barely able to stand, he went through his checklist, as he always did, ferrying equipment in stages to a spot well above both the high water line but below the dunes, and sent Collins their procedural safety check. He got into his silver-lined bivy bag, shaking from hypothermia, and fell fast asleep. Eight hours later, he woke up, and tested the right hip. Horrendous. He said to himself, Here we go, Nags—we're headed to OT.

Morning scene at Shagwong Point, Montauk, New York.

Morning scene at Shagwong Point, Montauk, New York.


How does he do it? How? Stroke after stroke, hour after hour, day after day. Alone. Carbohydrate powder for food, rationed water to drink. Between a relentless sky and an unforgiving sea. Physically drained but mentally stoked, constantly running down a navigation checklist of wind switches and swell movements. Lots and lots of math. And still there is "enough time out there to think about probably every thought I've ever had," Nagler says.

Nagler often says what drives him to pursue his ultra-endurance endeavors are the prospects of "brutality and beauty right next to each other."

The moments when the sunrise bathes the whole sky in pink and orange and there is nothing else visible except the water stretching toward the horizon as calmly as a carpet. Such rare visions reward the many hours of torturous effort, through the darkness and the cold. "Diametrically opposed forces are right next to each other pretty much the whole time," Nagler says.

Nagler's epics also always have a "mission," in this case raising funds to support those islanders who cannot afford to pay for services at a Nantucket nonprofit called Fairwinds, a community-based mental health clinic and addiction treatment center. The choice was obvious—Nagler doesn't hesitate to discuss his own struggle with depression and psychological challenges, and remains committed to removing the stigma around therapy and mental health.

"I believe therapy has value for every person," Nagler says. "Don't shut it out just because it hasn't been in your life before or you feel it's voodoo. If you shut it out, you will have limitations on your personal growth for the rest of your life."

He ultimately raised $74,600 for Fairwinds, more than twice his goal.

The stretch between Menemsha, Martha's Vineyard, and Nantucket harbor is 41 miles, took 19 hours to paddle, and like many other legs, it was hairy. Hundreds of seals danced around his board as he passed Muskeget Island and then crossed the Madaket flats, which put him on high alert for "Whitey Bulger," says Nagler. He never did see a fin, but you can be sure "the fins" saw him.

Nagler's arrival at Brant Point Light with a welcoming crowd after his long journey to raise funds in support of Nantucket counseling center Fairwinds. FAIRWINDS-NANTUCKET'S COUNSELING CENTER

Nagler's arrival at Brant Point Light with a welcoming crowd after his long journey to raise funds in support of Nantucket counseling center Fairwinds. FAIRWINDS-NANTUCKET'S COUNSELING CENTER


Around 6 p.m. on July 27, Nagler could finally see it—the Brant Point Lighthouse framing the inner harbor. A boat came out to greet him and families cheered from shore. He had grown a thick beard and lost 37 pounds on the 24-day journey, but he cracked a wide smile when his friend, Jim Mondani, doused his head with Champagne. "I couldn't really collapse in a heap, because I had this group around me shaking my hand, and I still had to go through the checklist."

Nagler gets gets doused with Champagne by a friend after arriving at Nantucket's Brant Point. KIT NOBLE PHOTOGRAPHY

Nagler gets gets doused with Champagne by a friend after arriving at Nantucket's Brant Point. KIT NOBLE PHOTOGRAPHY

Four hundred and sixty-five miles were behind him. And yet Nantucket was only the turnaround point, a place to recuperate for four days before he cast off to suffer again. He finally stopped in Sagaponack, New York, another 260-mile push.

But Adam Nagler is nowhere close to finished.

Zach Schonbrun '05 is a senior editor at The Week magazine.