John John Florence’s new racing catamaran was absolutely hauling along the east side of Oahu. Or at least it seemed to be. There were 15 boats in the race, and I watched from the cockpit as John John worked the wheel, defending a position near the front of the pack.

We’d just rounded Kahuku Point, and the shelf fell away, turning the water from sky blue to dark

purple. There were now 90 miles of open ocean between us and the finish line on Kauai.

I looked over at Joey Cabell, 80. The 1960s surf legend seemed restless. Bored, even. He hung back in the cockpit and watched dully as John John took advice from Patrick Murray, the professional sailmaker he’d invited along to coach him.

Joey’s eyes drifted to the billowing sails, the darkening clouds, and the assorted guys sprawled across the aft sofa.

“You want some coffee?” came a voice from the sofa.

The octogenarian eyed the espresso machine next to the Vitamix, the distended bag of gourmet beans. “Sure,” he said. We got the impression he thought we were soft. The sailmaker said something to John John, who shouted the translation over the wheel to the pit, where musician Jack Johnson and professional waterman Kai Lenny, keen to learn the ropes, were cranking winches and cleating sheets.

At 25, John John was widely regarded as the best surfer in the world. By the age of 12, he’d already been on the cover of Surfer magazine and was making six figures in sponsorships. His earnings helped support his family, and the industry saddled him with predictions of a career that sounded like fantasy. The pressure on him as a kid was tremendous.

He’s certainly not the first surf prodigy from Hawaii to get smothered in hype, but he’s arguably the first to have ridden out of it well. And that’s led to questions. Like, why didn’t he try to punch the release valve with drugs or hide out in a myriad of dysfunctional relationships? The list of prodigies who’ve so fallen is staggering.

I have a theory. I think he survived by finding immense satisfaction in arenas beyond surfing.

He’s remarkably well read. He’s fascinated by analog photography to the point of building a darkroom in his garage. He sails Hobie catamarans so hard that the company sends him boats to test.

While others may have found themselves contained by surfing, defined by it, John John seems more expansive, more intrigued by the vastness of learning, trying, and adapting. Surfing, it seems, is just one outlet among many.

I think that’s why, when he tore his ACL during a 2018 free surf in Bali, rather than dwell on all the comps and waves he was going to miss, he simply turned his attention to other passions. He added prone paddleboard racing to his list of hobbies and quickly became competitive in it.

Whether or not you buy that theory, what John John had accomplished is indisputable. He’d fulfilled the commentators’ wildest predictions and then some, winning back-to-back world titles in 2016 and 2017. His earnings had afforded him the Vela — the 50-foot South African gunboat, which he’d bought from pro snowboarder Travis Rice, and at whose helm he now stood.

The sky darkened. The swells grew taller, tighter. Mist shot over the gunwales. Bright constellations of foam formed on the surface of the deep. Joey watched silently as the radio crackled with news that two crews were withdrawing due to the conditions.

Finally, Joey spoke. “Are we racing?” he asked. “Or just cruising?”

We all glanced at each other.

“We’re racing,” John John said.

“Oh,” Joey said. He sipped his coffee.

The cockpit was quiet. John John made a few uncertain

adjustments with the wheel, turned to look back at Joey, and said, “What are you thinking?”

The old man looked triumphant.

Joey is a legend among surfers and sailors. He’s quietly articulate and, like John John, he is both singular — almost tunnel-visioned — in his drive and sweepingly well-rounded

in his pursuits.

Decades ago he was unbeatable in surfing and alpine ski racing. He bounced back and forth between Hawaii and Colorado, competing as he co-founded the first Chart House restaurant in Aspen.

While building out the second location in Honolulu, he decided to compete in the Duke Kahanamoku Invitational Surfing Championship as a way to promote the grand opening. The night before, he shaped and glassed a board in the kitchen of his unfinished restaurant and rode it that morning — still tacky — to a first-place finish.

The restaurant succeeded. In the following decades, Joey’s drive pushed him into auto racing, spearfishing, and sail racing. He still holds the speed record for sailing from Tahiti to Hawaii in a catamaran he built himself.

Joey told John John exactly what he was thinking. “I want more sail. Let’s hoist the full main.”

The young man nodded, and the crew scrambled from the sofa. The mainsail flapped in the wind and twisted around bodies and ropes until they got it raised.

Then Joey said something about the spinnaker. There was more commotion, and we were really running now. But unlike monohulls, catamarans can capsize. You have to stay on it. Joey stepped forward and stood beside John John. They both spoke calmly and gestured with long, wiry arms; both wore Mad Hatter grins as they peered out at the waves. They were Renaissance men. 

“Ease up,” Joey said. “Ease up. Hold. Now fall off, just a little. Don’t overcorrect.”

The Vela rocketed up a wave, pointing straight at the sky. Then it tipped and we were plunging, aimed into the abyss.

The sails howled. The force of the wind pulsed down the mast and hummed right up through the floor into our shins. The sailmaker looked nervous. The rain began to fall. After an hour or so, John John asked Joey if he wanted the helm. The old man’s eyes lit up, he grabbed the wheel, and with a few tweaks, everything tightened up. The halyards creaked, the sails hissed, water seethed over the hulls. Waves smashed up through the trampoline. It was a different vessel entirely. The sailmaker started saying, “Oh shit, oh shit,” under his breath.

Joey was whispering something, too. “Pushing it,” he said. “Pushing it.”

The rain got heavy, and Jack and Kai came in from the pit, soaked. We crowded around as Joey conducted the Vela like some enchanted wizard, his gray hair raked by the wind, his ice cube eyes shot wide and unblinking.

We’d taken a route 3–5 miles north of the other competitors and hadn’t seen any other boats for some time. But as we closed in on the finish at Nawiliwili Harbor, two sails appeared.

The wind abated, the waves petered, and we saw we wouldn’t catch the leader. But there in second place was our friend Dawson Jones.

John John retook the wheel and we began hunting him. About a mile from the finish we were neck and neck, and it was a game of chicken to see who would drop their spinnaker first. We went for it, and our spinnaker halyard was severed. The massive sail blasted about, weaving a web of tangled lines and fabric, and someone shouted at Jack to cut it. “Cut what?” he shouted back.

“The spinnaker sheet!” 

Jack found a knife and finished the work, but we were now a boat length behind Dawson.

John John tried to close on him, calmly giving orders, but we gained no ground. The harbor entrance and the finish line were just ahead, and we all held our breath, thinking, “They

have to drop it sometime, right?”

And just like that, their spinnaker plummeted, unspooling into a nest of ropes and sails. Dawson’s boat lurched sideways, and it looked like someone went overboard. We hooted and

yelled and pinned it past them into the harbor, taking second.

The race wasn’t an important one. There were no news crews, no stakes, just a competition for its own sake. It ended with a simple barbecue deep inside the harbor.

Between mouthfuls of burger, John John pestered the hosts about the second-place medal. He didn’t want to leave without it. Sure, it was just a piece of kitsch from an obscure race that

no one aside from the competitors would remember. But it meant something to him: progression, a totem of his drive. 

Some time later, John John and his crew were back on the Vela. A boat pulled up beside us, and a passenger asked, “Who’s the captain?” We looked at John John. He poked his head out of the cockpit and paused, thinking.

Then a smile found his face. “We all are,” he said.