Big Island Jack | Going The Distance By Keith Holland

Big Island Jack Going the Distance
Global Partner

From the Issue: Standup Journal Winter 2008-2009

Jack Gillen attended Princeton High School in Cincinnati Ohio, and by his own admission, was a somewhat directionless, underachieving, often in trouble kid. Fortunately, Jack found solace and camaraderie on the high school swim team where he was an average swimmer at best. Jack’s teammate, Art Miller, became of one his closest friends.

It was in 1973 that two previous Princeton High grads, Jeff Lischer and Mike Miller (Art’s older brother) moved from Cincinnati to Oahu. Mike would tell his younger brother tales of Hawaii. Art would filter those tales to his close friend and teammate, Jack.

In 1977, after graduation, Art followed his older brothers’ footsteps and went to Hawaii. Jack stayed in Cincinnati. Art called one bleak Cincinnati day and told Jack if he wanted it, he had a job, teaching tourists to scuba in Oahu’s Haunama Bay. Jack quit making donuts on the graveyard shift and flew to Oahu.

Big Island Jack | Going the Distance 1
MIKE MARSOUN (Left) Mid-channel energy bar toss during the Molokai-to-Oahu race.
It was at Magic Island, on Oahu, that Jack looked out over the turquoise water, walked the warm sandy beach, looked up at the crystal clear, bright blue sky and said out load, to nobody, “I am NEVER leaving.”

At Makapuu Jack’s connection, relationship and bond to the ocean became permanent. As a competitive swimmer and scuba instructor, Jack says, “It was natural to put fins on and body surf. It was total love, sliding down the big faces at Makapuu, just me and the ocean… and at one point, it was like an epiphany. I realized I was actually connected to nature and the ocean. My life as a kid with no direction was over. I got a new start somehow, a clean slate.”

Jack eventually did leave Oahu, but not Hawaii. He went south to the Big Island. Other members of the Princeton High Swim Team had moved there from Oahu to “get away from the city and all its various forms of temptation.”

On the Big Island, Jack landed a job lifeguarding at the swank Mauna Kea Beach Hotel. Sweet waves break in the bay off that Hotel, and when Jack wasn’t rescuing tourists, he continued to push his limits body surfing.

Jack eventually got into six-man outrigger canoes. Soon after, single man outriggers got his attention.

After 25 years of body surfing and paddling canoes, Jack saw a picture of someone surfing perfect overhead Pipe.

Jack instantly felt that there should be something under his feet, so he took up surfing. He gave surfing a year or two but says, “I never really got it.

When the conditions were good the Big Isle lineups were gnarly and crowded. When the conditions were bad, surfing wasn’t really an option.”

So Jack moved on.

Sandwich Island Composites shaping bay
DAN RAYBURN: Jack (on right) in the Sandwich Island Composites shaping bay with Maui designer Mark Raaphorst (in back) and New Zealand’s Campbell Farrell (5th in the Naish Maliko race), discussing Gillen’s new F-18, a 17’6” x 26-1/2” distance-racer, displacement bow that features a planing-tail for wave riding. “How do we go faster, farther with fewer strokes? That’s always the question,” says Raaphorst.

“I realized I was actually connected to nature and the ocean”

Determined to keep his connection with the ocean, he bought a stock 12-foot prone paddleboard from legendary prone (laying down) paddleboarder, Bob Hogan. Seven days later Jack entered a three-mile paddleboard race on the Hilo side of the Big Island. After the race, Jack returned the paddleboard to Bob and said “Paddleboarding is way too grueling” and he was “done with it forever.”

But Jack eventually gave paddleboarding another shot, and the second time around he actually trained before racing and realized “it was doable…” Jack paddled 12-foot prone boards then moved to 18-foot Australian knee paddling. Once on the knee paddling boards, things changed for Jack. “I could see what was going on, look around a little. I could change my body position more, it was more comfortable for me, and the glides were incredible.”

Marsoun Via Sup Boards
MARSOUN Via sup boards, Gillen and others—Laird included—escorted the swim portion of last year’s Ironman World Championships held on the Big Island each October. “Standup boards have become the perfect Ironman security and race vehicle,” says Jack. They are also utilized as pace care: guys on sup boards “paddle in front of the swim pack dragging a long pink tape which the swimmers use to guide them along.”
Fast forward to the 2004 Molokai to Oahu race where Archie Kalepa decides he’s going to be the first guy to ever standup paddle the race. As a knee-paddling competitor in the race, Jack saw the spectacle and comments: “It definitely was not love at first sight, though for me the timing was perfect.

I’d paddled six man and single man canoes. I had been prone paddling for a few years, and now was knee paddling, but none if it was surfing. Prone and knee paddling were great, but I also was missing holding a paddle, though not enough to get back into it.”

Jack ordered his first standup board, and after months of waiting finally got his Ron House, a 12 foot by 26 inch wide, 50 plus pound glass board. The first day Jack went to use it, he couldn’t get it off his truck, it was too big for him to handle by himself.

“So here I am,” Jack says, “I got my new board, I’m in Kukio, near the Four Seasons, and I can’t get my board off the roof of my truck. I find some tourist and ask for help to get the thing down. The tourist was like, ‘you look like a surfer, but you can’t get your board off your roof?’” Jack continues, “The wind is onshore, there is this two-foot junk wind swell rolling in off the point. Of course, no one is out. I somehow manage to get my board to the water, try and stand up on the thing, and it’s way too tippy. I’m just falling off. So I lay down, and with my prone paddling experience I head out through the chop—spray coming over the front of the board—and see if I can get a wave off the point.”

That first ride is etched into his memory. “There was so much happening when I linked up those first few glides… Before I knew it, I’d made it back to the beach, and it wasn’t actually until I hopped off my board that it hit me. The feeling was like I had just received some gift like I found money on the sidewalk or something, and immediately I thought ‘this is IT,’ and ‘I want more of THAT,’ so I paddled out for more…”

It was at Jack’s second Molokai to Oahu crossing (again in the 18-foot knee paddle division) that he saw Kevin Horgan of Kauai become the first ‘official’ solo standup entry in the race. After the event, Jack found Kevin’s contact info and gave him a call. Kevin invited Jack over to Hanalei Bay, to talk story and check out standup gear. He also let Jack know the board used to do the crossing was for sale. Jack’s immediate response was, “I’ll take it!”

On Kauai, Kevin also had Jack try a 9’6” fish. That fish board enabled Jack to get what he describes as “unbelievable rides… That board changed everything.

It felt like surfing… It was not at all like riding a twelve-foot single fin.” As soon as Jack got back to the Big Island, he called Ron House and asked him to shape a 9’6” by 27.5” quad-fin, winged swallowtail fish. That board made it to Jack just before Christmas of 2005 and he could actually stand up and paddle the board, get to where he wanted and ride some waves.

“It was like Tiger Woods asking me if I wanted to join him for a round of golf” –Jack on being asked by Ekolu Kalama to join him on a paddle to Molokai

After that, Jack wanted to talk to anyone who was willing to shape him a board and he started acquiring boards as fast as he could get them. An earlier sale of property Jack had, and a booming Big Isle window cleaning business created the means to stockpile boards at will. Jack’s understanding of the sport, ability, and collection of boards, escalated rapidly.

The 2006 Molokai to Oahu crossing was approaching. Jack was going standup, as were a few other competitors. Ekolu Kalama was one them, and he gave Jack a call suggesting that they train by crossing from Maui to Molokai on their standups.

The week prior, they had entered the Maliko to Kahului race, and their boards now needed to get from Maui to Molokai. “That call from Ekolu was like Tiger Woods asking me if I wanted to join him for a round of golf. Of course, I said yes I’d go Maui to Molokai. I felt like it was an honor just to be asked.”

RON DAHLQUIST Jack, using his bamboo paddle, placed 11th overall in July’s Naish International Maliko race.
RON DAHLQUIST Jack, using his bamboo paddle, placed 11th overall in July’s Naish
International Maliko race.

Ekolu’s cousin, Dave Kalama, dropped the two at Flemings Beach, on Maui, and off they went. No escort boat, no one else, just the two of them, no problem?

Halfway across the Alanuihaha Channel the wind is howling, the rain squalls are blowing through, and the channel has a building swell. Ekolu is riding one of the first-foot steering standup boards available, while Jack is riding a traditional open ocean board. Ekolu can stay upwind more easily than Jack, and the wind is pushing hard. At one point, the two get separated. Between the swells, they cannot see each other. Ekolu has a higher line, while Jack is being pushed downwind. “And did I mention I didn’t exactly know where we were going?” Jack asks with a grin. “Ekolu’s parents were going to pick us up on Molokai, and Ekolu knew the beach and the course to get there, but I didn’t.

I was trying to follow him, but was having a hard time staying upwind. Then we got separated for what seemed like forever, and after some time, I honestly thought I might die.”

Jack continues, “I just tried to stay focused on what I was doing, riding these enormous open ocean swells, just rolling in across the channel. And finally, I’ll never forget it, in the distance, I see Ekolu, dropping into this BOMB and just riding it FOREVER, and I think ‘Wow, that swell is HUGE, and Ekolu is just RIPPING! This is followed right away by ‘and I’m going to LIVE!!!!!’” Jack’s connection to the water is at the core of what drove him to pursue standup with such passion. And he’s totally stoked about the crossings he’s done, the waves he’s gotten, and the boards he’s collected. But Jack’s greatest rewards have been from the people he’s met through standup paddling. The opportunities he’s had to, as he puts it, “rub shoulders with some truly great watermen.” Jack speaks humbly about a session he had on the Big Isle with surf pro Rob Machado. After being invited to paddle out to an outside reef by Rob, Jack got to “see just an unbelievable and incredible display of standup surfing.

“I might not have all the talent that some of the guys I get to paddle with have, but I am for sure just as stoked”

The guy just took it to another level.” Jack also realizes his good fortune at having Ekolu Kalama take him under his wing. And the time on Kauai with Kevin Horgan, that was a privilege to Jack.

And he realizes if it weren’t for standup, the excitement of working with notable shapers on new designs would not have happened.

Gillen with wife Terry
MAKENA MARSOUN Gillen with wife Terry, a world class hula dancer, after Jack completed the ‘07 Molokai to Oahu race. “She has been at the finish line for all seven of my crossings,” notes Jack.

Another interesting aspect Jack ponders is that individuals currently involved in standup paddling are actually making surf history.

“Think about it” he says, “The sport is evolving so quickly, it’s exploding really, and I am lucky enough to have been there close to standup paddling’s birth, or rebirth, put more accurately.

I’ve been blessed with the means to pursue it. And though I might not have all the talent that some of the guys I get to paddle with have, I am for sure just as stoked. Maybe even MORE stoked on standup than they are.” And stoked he is, his collection of 35 boards attests to that. Yes, 35 standup boards! Jack has the boards spread out, some on the Big Isle, some on Oahu, and a few on Maui. He’s teaching standup to anyone who will let him, and constantly looking at whatever new product is available.

Jack’s created two businesses in the industry: Nature’s Carbon Fiber (NCF), paddles with a carbon blade and bamboo shaft, and Wave Chi, which combines Tai Chi, Indian club swinging, and standup paddling. The guy is totally fired up with no sign of slowing down. He’s just doing what he feels he was, and is, meant to do, and that’s standup paddle in all its forms.

Previous articleUnforgettable Sup Expedition on the Breathtaking Maine Island Trail
Next articleGet Stoked on Summer! Standup Journal’s summer issue “Open Rangers” is ready to land
Standup Journal is the world's first and highest quality sup publication that is passionately following and writing about this special lifestyle, the culture, and the adventure and lifelong friendships we share!