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SF Chronicle, By Bruce Jenkins

October 17, 2016 Surfer Kai Lenny at Ocean Beach in San Francisco, Calif., on Monday, September 19, 2016. Lenny will be competing in the Red Bull Heavy Water stand up paddle board competition that has competitors paddling from Ocean Beach to just past the Golden Gate Bridge. Photo: Carlos Avila Gonzalez, The Chronicle

The stage is set for Kai Lenny to meet the challenge of San Francisco’s Ocean Beach. There could be no greater example of man against the sea.

To meet him up close, there’s nothing particularly imposing about Lenny, who stands 5-foot-8. Mostly you notice his charm, breezy confidence and stoked-on-life outlook. But this exceptional Hawaiian waterman is the centerpiece of the Red Bull Heavy Water event, a World Championship Series stand-up paddling race scheduled to begin at 10 a.m. Tuesday.

There hasn’t been an ocean race quite like this one, and it’s safe to say a few of the 40 competitors will not be demanding an encore. Ocean Beach, one of surfing’s great endurance tests, will make sure of that.

Riding thick, 12-foot boards, standing tall and propelling themselves with long, sturdy oars, the competitors will attempt to negotiate Ocean Beach’s relentless surge, paddle around a buoy just beyond the breaking surf and ride waves (just one, with luck) back to shore. Then they’ll be asked to do it again. The event requires a swell producing at least 10-foot faces, so it’s little wonder Lenny calls the challenge “intense. The heaviest stand-up paddle race of all time.”

And, yes, in order to begin the second phase of the race — an all-out sprint to the Golden Gate Bridge — riders will have to paddle out at Ocean Beach a third time. Ask anyone who surfs the place regularly at size; that’s downright sinister.

Great waterman meets Ocean Beach challenge

Media: Bruce Jenkins

With any type of swell in progress — this one figures to be right around the 10-foot criterion — Ocean Beach regulars prepare themselves for an arduous task. The oncoming lines of whitewater rarely stop, and it takes a lull in the action, or perhaps a convenient outgoing riptide, to create a paddling window. It generally takes surfers at least 20 minutes to reach the lineup. Some have dealt with the elements for an hour. The mere act of completing the paddle-out is cause for celebration, and everyone has a story of being denied, paddling back to the beach and hoping for better luck next time.

Remember, too, that conventional surfers ride streamlined boards in the 8-foot range. Trying to clear all this madness while stand-up paddling, on bulky boards hardly designed to “duck-dive” under waves, amounts to a gargantuan feat. A few stand-up surfers have pulled it off on big days, notably Mavericks pioneer Jeff Clark, but it’s a rare sight to see SUP action at sizable Ocean Beach.

“They’re gonna run it when it’s the biggest and nastiest,” said Lenny, smiling broadly, during a recent interview at the foot of Lincoln Avenue. “I love it!”

The start is likely to take place at the north end of the beach, in front of the Beach Chalet restaurant, to allow for maximum spectator viewing. It could be moved to the middle stretch, where the surf is invariably larger, to meet the 10-foot criterion. This is a 7.5-mile event, competitors heading northward past Lands End, racing underneath the bridge, ideally catching a final wave at Fort Point and finishing at the St. Francis Yacht Club.

NEW YORK, NY - AUGUST 20:  Stand-up paddle surfer Kai Lenny competes in SEA Paddle NYC in which TAG Heuer is the Official Timepiece and Official Timekeeper on August 20, 2016 in New York City.  (Photo by Eugene Gologursky/Getty Images for Tag Heuer) Photo: Eugene Gologursky, Getty Images For Tag Heuer
Photo: Eugene Gologursky, Getty Images For Tag Heuer
NEW YORK, NY - AUGUST 20: Stand-up paddle surfer Kai Lenny competes in SEA Paddle NYC in which TAG Heuer is the Official Timepiece and Official Timekeeper on August 20, 2016 in New York City. (Photo by Eugene Gologursky/Getty Images for Tag Heuer)

There are several noteworthy characters in the world-class field, including Hawaiians Zane Schweitzer, Mo Frietas and Connor Baxter, who won the 2014 world-tour championship and holds the lead in this fourth and final race of the series. Denmark’s Casper Steinfath is the current tour rankings leader and Australia’s Travis Grant also represent formidable threats in the open ocean.

But it’s Lenny, currently standing third and still in the title running, who attracts special attention wherever he goes. Seasoned observers don’t hold back in their comparisons, calling up the likes of Duke Kahanamoku and Laird Hamilton, for Lenny is a true original, his talents both astounding and distinctive.

By the time he was 10, Lenny was accomplished at longboard surfing, shortboard surfing, windsurfing, kite surfing, stand-up surfing and stand-up paddling. He holds the world record for the treacherous 32-mile SUP race from Molokai to Oahu, and has won three of the past four world-tour championships. He surfed the fabled big-wave spot “Jaws,” on his home island, more than 20 times in giant conditions last winter. And in February, when Mavericks produced perhaps its most spectacular day ever, Lenny was among the standouts taking on 50-foot faces off the coast of Half Moon Bay.

That’s not a personal resume. For a man who just turned 24, that’s some sort of fantasy.

Appropriately named — Kai means “ocean” in Hawaiian — he comes from Maui, where high-wind conditions are prevalent and fairly invite young surfers to expand their options. Growing up around the likes of Hamilton, Dave Kalama, Pete Cabrinha and Robby Naish at the forefront of wave-riding innovation, Lenny had all the inspiration he needed. To have such widespread expertise gives him singular status among his contemporaries, and the aforementioned feats only scratch the surface of his accomplishments.

“Being around all those guys, from the time I was a little kid, I always wanted to do everything that makes a true waterman,” he said. “And I’ve tried to be creative in each sport, trying to figure out new ways of riding waves.”

The Kalama connection points directly to Kai’s father, Martin, who went on a windsurfing vacation from his Santa Barbara home to Maui in 1985 and never left. He and the soon-to-be-iconic Kalama were part of a generation windsurfing Hookipa and drawing worldwide attention. Martin’s wife, Paula, also thrives in the ocean sports, “so Kai was pretty much doomed,” Martin said, laughing. “He was going to be in the water. Not that he minded. From the beginning, he put every bit of his energy into that.”

Martin, who works in real estate, describes his heritage as “Mexican, German and Prussian; I’m pretty much a poi dog. It’s a little more organized on Paula’s side: Italian and Slovakian. So Kai’s got a pretty interesting mix.”

And what really grabs people’s attention, beyond the magnitude of his career, is his personality. “He reminds me so much of Jay Moriarity,” said San Francisco’s Grant Washburn, referring to the storied Mavericks surfer who died on an international surfing trip in 2001. “Just a big smile on his face all the time, and totally genuine.”

Clyde Aikau, at 66, the front man for one of Hawaii’s most distinguished surfing families, calls Lenny “the perfect waterman. Does everything, big waves, small waves. And he’s a nice guy who says, ‘Hi,’ to everybody. He’s not on a high maka maka trip.” (The word means “eye” in Hawaiian —thus to dismissively look down one’s nose at people.)

Kahanamoku was a champion Olympic swimmer and goodwill surfing ambassador in the early 20th century, representing the very best of Hawaii. “Kai seems to have that quality about him,” said Bianca Valenti, the best of a fast-rising class of women surfing big waves in the Bay Area. “I’m so impressed by him. He’s like the modern-day Duke.”

Pacifica’s Steve Dwyer, rich in big-wave experience, was in the water all day Feb. 4 when Mavericks delivered to perfection with at least 50 surfers in the lineup at any given time. “Kai did the best and most intelligent surfing of them all, and it was only the second time he’d ever surfed there,” Dwyer said. “He took off on big, smart waves, consistently, the whole day.”

Because nothing strikes the public’s fancy quite like a human being cascading down a monumental wall of water, that might be Lenny’s most conspicuous calling card. The World Surf League held two of the most significant paddle-surfing events in history over the past year, in near-maximum conditions at Jaws and Puerto Escondido (Mexico), and Lenny held his own in both.

So the question comes to him, as it does to all big-wave surfers: When you’ve been held underwater too long, more than a minute, and you really need a breath, what goes through your mind?

“Well, you can’t panic,” he said. “To start thinking, ‘This is the heaviest thing ever,’ you can’t go there. I know that I wouldn’t be out there if I couldn’t survive anything I get myself into. Usually I’m thinking, ‘This is really uncomfortable,’ (laughter) or ‘After this, I’m definitely gonna take a break.’ Maybe grab a burrito or something. But I usually end up going right back out, anyway.”

Such confidence. Such a man apart. That’s Kai Lenny.

Bruce Jenkins is a San Francisco Chronicle columnist.

SF Chronicle, By Bruce Jenkins

October 17, 2016 Surfer Kai Lenny at Ocean Beach in San Francisco, Calif., on Monday, September 19, 2016. Lenny will be competing in the Red Bull Heavy Water stand up paddle board competition that has competitors paddling from Ocean Beach to just past the Golden Gate Bridge. Photo: Carlos Avila Gonzalez, The Chronicle

The stage is set for Kai Lenny to meet the challenge of San Francisco’s Ocean Beach. There could be no greater example of man against the sea.

To meet him up close, there’s nothing particularly imposing about Lenny, who stands 5-foot-8. Mostly you notice his charm, breezy confidence and stoked-on-life outlook. But this exceptional Hawaiian waterman is the centerpiece of the Red Bull Heavy Water event, a World Championship Series stand-up paddling race scheduled to begin at 10 a.m. Tuesday.

There hasn’t been an ocean race quite like this one, and it’s safe to say a few of the 40 competitors will not be demanding an encore. Ocean Beach, one of surfing’s great endurance tests, will make sure of that.

Riding thick, 12-foot boards, standing tall and propelling themselves with long, sturdy oars, the competitors will attempt to negotiate Ocean Beach’s relentless surge, paddle around a buoy just beyond the breaking surf and ride waves (just one, with luck) back to shore. Then they’ll be asked to do it again. The event requires a swell producing at least 10-foot faces, so it’s little wonder Lenny calls the challenge “intense. The heaviest stand-up paddle race of all time.”

And, yes, in order to begin the second phase of the race — an all-out sprint to the Golden Gate Bridge — riders will have to paddle out at Ocean Beach a third time. Ask anyone who surfs the place regularly at size; that’s downright sinister.

Great waterman meets Ocean Beach challenge

Media: Bruce Jenkins

With any type of swell in progress — this one figures to be right around the 10-foot criterion — Ocean Beach regulars prepare themselves for an arduous task. The oncoming lines of whitewater rarely stop, and it takes a lull in the action, or perhaps a convenient outgoing riptide, to create a paddling window. It generally takes surfers at least 20 minutes to reach the lineup. Some have dealt with the elements for an hour. The mere act of completing the paddle-out is cause for celebration, and everyone has a story of being denied, paddling back to the beach and hoping for better luck next time.

Remember, too, that conventional surfers ride streamlined boards in the 8-foot range. Trying to clear all this madness while stand-up paddling, on bulky boards hardly designed to “duck-dive” under waves, amounts to a gargantuan feat. A few stand-up surfers have pulled it off on big days, notably Mavericks pioneer Jeff Clark, but it’s a rare sight to see SUP action at sizable Ocean Beach.

“They’re gonna run it when it’s the biggest and nastiest,” said Lenny, smiling broadly, during a recent interview at the foot of Lincoln Avenue. “I love it!”

The start is likely to take place at the north end of the beach, in front of the Beach Chalet restaurant, to allow for maximum spectator viewing. It could be moved to the middle stretch, where the surf is invariably larger, to meet the 10-foot criterion. This is a 7.5-mile event, competitors heading northward past Lands End, racing underneath the bridge, ideally catching a final wave at Fort Point and finishing at the St. Francis Yacht Club.

NEW YORK, NY - AUGUST 20:  Stand-up paddle surfer Kai Lenny competes in SEA Paddle NYC in which TAG Heuer is the Official Timepiece and Official Timekeeper on August 20, 2016 in New York City.  (Photo by Eugene Gologursky/Getty Images for Tag Heuer) Photo: Eugene Gologursky, Getty Images For Tag Heuer
Photo: Eugene Gologursky, Getty Images For Tag Heuer
NEW YORK, NY - AUGUST 20: Stand-up paddle surfer Kai Lenny competes in SEA Paddle NYC in which TAG Heuer is the Official Timepiece and Official Timekeeper on August 20, 2016 in New York City. (Photo by Eugene Gologursky/Getty Images for Tag Heuer)

There are several noteworthy characters in the world-class field, including Hawaiians Zane Schweitzer, Mo Frietas and Connor Baxter, who won the 2014 world-tour championship and holds the lead in this fourth and final race of the series. Denmark’s Casper Steinfath is the current tour rankings leader and Australia’s Travis Grant also represent formidable threats in the open ocean.

But it’s Lenny, currently standing third and still in the title running, who attracts special attention wherever he goes. Seasoned observers don’t hold back in their comparisons, calling up the likes of Duke Kahanamoku and Laird Hamilton, for Lenny is a true original, his talents both astounding and distinctive.

By the time he was 10, Lenny was accomplished at longboard surfing, shortboard surfing, windsurfing, kite surfing, stand-up surfing and stand-up paddling. He holds the world record for the treacherous 32-mile SUP race from Molokai to Oahu, and has won three of the past four world-tour championships. He surfed the fabled big-wave spot “Jaws,” on his home island, more than 20 times in giant conditions last winter. And in February, when Mavericks produced perhaps its most spectacular day ever, Lenny was among the standouts taking on 50-foot faces off the coast of Half Moon Bay.

That’s not a personal resume. For a man who just turned 24, that’s some sort of fantasy.

Appropriately named — Kai means “ocean” in Hawaiian — he comes from Maui, where high-wind conditions are prevalent and fairly invite young surfers to expand their options. Growing up around the likes of Hamilton, Dave Kalama, Pete Cabrinha and Robby Naish at the forefront of wave-riding innovation, Lenny had all the inspiration he needed. To have such widespread expertise gives him singular status among his contemporaries, and the aforementioned feats only scratch the surface of his accomplishments.

“Being around all those guys, from the time I was a little kid, I always wanted to do everything that makes a true waterman,” he said. “And I’ve tried to be creative in each sport, trying to figure out new ways of riding waves.”

The Kalama connection points directly to Kai’s father, Martin, who went on a windsurfing vacation from his Santa Barbara home to Maui in 1985 and never left. He and the soon-to-be-iconic Kalama were part of a generation windsurfing Hookipa and drawing worldwide attention. Martin’s wife, Paula, also thrives in the ocean sports, “so Kai was pretty much doomed,” Martin said, laughing. “He was going to be in the water. Not that he minded. From the beginning, he put every bit of his energy into that.”

Martin, who works in real estate, describes his heritage as “Mexican, German and Prussian; I’m pretty much a poi dog. It’s a little more organized on Paula’s side: Italian and Slovakian. So Kai’s got a pretty interesting mix.”

And what really grabs people’s attention, beyond the magnitude of his career, is his personality. “He reminds me so much of Jay Moriarity,” said San Francisco’s Grant Washburn, referring to the storied Mavericks surfer who died on an international surfing trip in 2001. “Just a big smile on his face all the time, and totally genuine.”

Clyde Aikau, at 66, the front man for one of Hawaii’s most distinguished surfing families, calls Lenny “the perfect waterman. Does everything, big waves, small waves. And he’s a nice guy who says, ‘Hi,’ to everybody. He’s not on a high maka maka trip.” (The word means “eye” in Hawaiian —thus to dismissively look down one’s nose at people.)

Kahanamoku was a champion Olympic swimmer and goodwill surfing ambassador in the early 20th century, representing the very best of Hawaii. “Kai seems to have that quality about him,” said Bianca Valenti, the best of a fast-rising class of women surfing big waves in the Bay Area. “I’m so impressed by him. He’s like the modern-day Duke.”

Pacifica’s Steve Dwyer, rich in big-wave experience, was in the water all day Feb. 4 when Mavericks delivered to perfection with at least 50 surfers in the lineup at any given time. “Kai did the best and most intelligent surfing of them all, and it was only the second time he’d ever surfed there,” Dwyer said. “He took off on big, smart waves, consistently, the whole day.”

Because nothing strikes the public’s fancy quite like a human being cascading down a monumental wall of water, that might be Lenny’s most conspicuous calling card. The World Surf League held two of the most significant paddle-surfing events in history over the past year, in near-maximum conditions at Jaws and Puerto Escondido (Mexico), and Lenny held his own in both.

So the question comes to him, as it does to all big-wave surfers: When you’ve been held underwater too long, more than a minute, and you really need a breath, what goes through your mind?

“Well, you can’t panic,” he said. “To start thinking, ‘This is the heaviest thing ever,’ you can’t go there. I know that I wouldn’t be out there if I couldn’t survive anything I get myself into. Usually I’m thinking, ‘This is really uncomfortable,’ (laughter) or ‘After this, I’m definitely gonna take a break.’ Maybe grab a burrito or something. But I usually end up going right back out, anyway.”

Such confidence. Such a man apart. That’s Kai Lenny.

Bruce Jenkins is a San Francisco Chronicle columnist.

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