Issue 9.3: June/July 2006

King of the Hills

story by Ric Valdez
photo by Sergio Goes


It’s just your basic Friday afternoon over at Justin Lono’s place in Papakolea, the Hawaiian homestead neighborhood that sits in the shadow of Honolulu’s Mount Tantalus: Reggae playing from the boom box; cans of Hawaiian Sun juice lying around; a small crew of skaters hanging in the backyard, eyeing the rain-heavy clouds and discussing the possibility of an afternoon run down serpentine Tantalus Drive. Among them is Darryl Freeman, who is currently lounging in a hammock under a large mango tree, both hands tucked behind a mane of curly blond hair and his left leg confined in a blue fiberglass cast.

“I was skating down one of my favorite nighttime runs,” he says with a mischievous grin, when asked of his latest incapacitation. He swings out of the hammock, balancing on his one good leg. “I went down on my first power-slide: at about thirty-five (m.p.h.) my front foot slipped off my board. I cracked my ankle and caused extensive soft tissue damage. It’s been a few months since I walked, but I tried skating yesterday—I can’t walk, but I can still roll!”

Out of the water, stand-up, downhill skateboarding—“bombing”—is the closest thing to the thrill and danger of big wave surfing, and Honolulu’s Darryl Freeman is one of the sport’s kings. Since 1998, he’s been competing on the professional downhill skateboard circuit, covering the globe to challenge the best in the world … and winning: In 2002, he took a gold medal at the Gravity Games, which are widely considered to be the world championships of the sport; that year, he finished the world tour at first overall, a placing he would narrowly miss two years later.

All of which is pretty remarkable considering there is not one officially sanctioned downhill race in all of Hawai‘i—in fact, depending on the place and circumstances, street skating of any sort is only marginally legal in the Islands … and bombing is not at all. Let’s just say it: Most Honolulu residents, if they were to see Darryl on their street, would think he’s just another punk.

Bob Freeman says his son has always been fearless. “At three or four he would slide down the stairs on a boogie board, crash into the walls and do it again.” Darryl grew up on Maunalani Heights, at the top of Wilhelmina Rise—one of the state’s longest, straightest and steepest paved strips. When he needed to get down the hill, he simply skateboarded to the bottom. Long before he was competing, Freeman became a fixture on the hills of Honolulu, adorned in his helmet and thick welding gloves (far superior to standard skating pads when it came to breaking his falls), carving his way down at all hours and in all conditions.

But the world of professional downhilling is miles away from Wilhelmina Rise, both literally and figuratively. Founded in 1996, the International Gravity Sports Association’s world tour now covers the Continental United States, Canada, Europe, Brazil, Japan, Australia and South Africa. In the controlled racing world, competitors can reach speeds of more than seventy miles per hour on roads that are closed off and lined with hay bales to absorb the shock of high-speed crashes. Racers wear aerodynamic helmets and full-body leathers similar to those used by grand prix motorcycle racers. The courses themselves sometimes hit grades of up to twenty-five percent—by way of comparison, in most towns the steepest roads are in the six percent range; in Hawai‘i, to find roads that hit twenty percent, you need to climb Mauna Kea or descend into Waipi‘o Valley.

Berkeley Steve photo
Though it looks like mayhem, this is actually
a controlled braking slide by a trained

professional—in other words, don't try
it at home. Darryl Freeman, Honolulu.

Darryl’s first professional race was almost a missed opportunity. In October of 1998, he scraped together enough money for a plane ticket to Los Angeles, but had no ride to the competition site, 100 miles away in the parking lot of San Diego’s Qualcomm Stadium. Hopping a bus, a train and then hitchhiking, he reached the site of the X-Games just minutes before the first heats began.

“I ran up the hill with no idea what I was about to see,” he says. “At the starting gate were six riders wearing these leather suits and speed helmets. These guys didn’t make unnecessary turns or break speed at all: Within fifty yards they were beyond fifty miles per hour. They just blew past me: I didn’t even know that speed was possible.”

Actually, under normal circumstances, it’s not possible.

“Our boards are slightly longer than your average street skateboard, and are designed for racing at high speeds,” Darryl explains. “The bearings we use are made from a high tech ceramic that doesn’t transfer heat, so you don’t have to oil them on a short course [any run under a minute]. The wheels are made of an advanced urethane that can handle the high speeds without disintegrating—it would be disastrous to have your wheels overheat and melt down when you’re going over sixty.”

Darryl has known his share of disasters: Concussions, broken bones and so many scrapes on so much of his body that it’s as if he’s reading a road map as he recounts their various origins. Even so, he continues to win: In late 2004, back home in Hawai‘i on a break between the European and the South African leg of the tour, Darryl suffered a spinal disc-injury while free-skating at an O‘ahu skate park. Unable to compete in the World Finals in South Africa, he nonetheless ended the season with enough overall points to finish second in the world.

Darryl’s most recent injuries forced him to miss the entire 2005 season, but he admits that the time away from skating has affected him in some positive ways.

“I always have these good ideas of what I should do for the sport, but can never sit still long enough to take care of business because I just want to go ride my board. So now I’m designing a Web site, organizing events, getting equipment to amateur riders in the Islands and designing some new racing boards.”

After eight years on the racing circuit, Freeman allows that downhilling is still very much an underground sport, even on the professional level.

“There’s nobody making a living off of downhill skateboarding right now,” he says. “It’s a professional sport only in terms of the level of competition—you can win cash prizes, but usually they’re so minor, you’re lucky if it pays for your plane fare.”

And in spite of his youthful appearance, this stubble-chinned, thirty-year-old daredevil admits that past injuries are catching up.

“These last two injuries have been the most painful I’ve had. The back injury has been deadly: It had me lying on the floor for a month. I had some broken ribs, too, and any sneeze or cough hurt so bad. I think it’s time to start doing some light-weight training, more stretching … maybe yoga,” he says with that same playful grin. After so many injuries, one might wonder if it isn’t time to take up something a bit safer. But asked if he sees himself skating down Tantalus when he’s fifty years old, the smile only widens.

“Definitely … as long as I can.” HH

Darryl Freeman can be reached at