LATER THAT DAY, MacKenzie bounds up to the first tee with a round of "Hey, bros" for his partners, Eric Axley and Chris Smith. Like any serious golfer, he takes his time lining up his shots. He sprinkles grass blades to check the wind, settles his feet, steps back and repeats the process. But once he strikes his ball, he's back to being Willy Mac: shouting hello to a player on the next fairway over, flipping Spencer the bird and then quickly blowing her a "just kidding" kiss, giving me the classic bro shake after sinking a putt.

"I just think of it as snowboarding out there," he says. "Right to left, left to right. I try to envision the grass like a sea of fresh powder, and I'm going to point it into that beautiful wind lip and make one huge heel-side turn. That's how I work the golf course. But then I space out between shots. If I had to just dwell on golf the whole time, I'd really go psycho."

When MacKenzie first left North Carolina in his white 1986 Toyota minivan, he had no particular plan. He simply drove to the Rockies and began resort hopping. His first stop, Taos, New Mexico, seemed nice but didn't allow snowboarding ("See ya, Taos"). He continued on to Telluride, Colorado ("OK"), Crested Butte ("Hmmm, nice"), the resorts in Summit County ("Nah, this place is lame"), Steamboat ("Wasn't steep enough"), and Utah ("The vibe was just sort of dicey there"). He stayed in Jackson Hole, Wyoming, for a while, but mostly because he ran out of money and had to work at a Taco Bell ("Giving burritos to all the kids"). Finally, a month after leaving Greenville, he pulled into Big Sky, Montana ("Goddamn, this place is heaven"), parked his van in an empty corner of the ski-area parking lot, and unfurled his zero-degree bag.

"It wasn't unheard of for people to sleep in their cars there, especially in summer," recalls Jason Frounfelker, who worked with MacKenzie at Big Sky until MacKenzie got fired for showing up late. "But he was a rare breed in those winters. And he was a dirtbag. Tried to work whatever angles he could."

MacKenzie proudly claims that he was on his way to becoming Dirtbag King, a title bestowed upon the crustiest local every season. "You have to be a little older," he admits. "But I was already kind of legendary for having a couple of seasons when I didn't have a pass but still did like 100 days by poaching in the lift lines."

In the warmer months, he became a Class V kayaker and soon had work as a raft guide, following the spring and summer flows from Montana's Gallatin River to West Virginia's Gauley and, eventually, to the rivers back in North Carolina. At one point, he had to duct-tape padding onto his heels so he could paddle the day after a 15-foot rock-climbing fall. "We used to call Will our migrant worker," his mother recalls. "The snows would melt in Montana and he'd start heading south."

But one year he altered his orbit. In 1998 MacKenzie saved enough money to drive to Alaska, though not enough for lift tickets or lodging, let alone the helicopter rides he was after. So he built a snow cave outside Valdez, fired up his gas stove, and hoped for the best.

"I was hitching one day and this van picks me up," he says. It was pro snowboarders Noah Salasnek, Mike Devenport, and Johan Oloffson, who were in Alaska shooting with Standard Films director Mike Hatchett. "They gave me a ride back, and I broke down and said, 'Look, fellas, I came here to ride something sick. Is there some way I can get in y'all's group for one mission?' "

"We felt kind of sorry for him at first," recalls Hatchett, who ended up taking MacKenzie into the Chugach several times over the next three weeks. "But all the pros were stoked on him, because he was a really good rider and totally cool to hang out with. That's the only time we've ever taken anyone up for free."

MacKenzie still refers to Alaska as the best trip he's ever taken, both for the riding and for the career turning point it would prove to be—after five seasons, he decided not to return to Big Sky for another winter. Instead he moved back home, making enough cash selling Christmas trees to fund a three-month surfing trip to Costa Rica. There he met a tourist from California who said he'd made a fortune importing stretchy Costa Rican hammocks into the U.S. Three months later, MacKenzie had gone broke trying to sell them door to door in North Carolina, home to Hatteras Hammocks, the largest hammock company in the world.

"That didn't work out so well," he recalls, chuckling. "I was having an early midlife crisis, like, Am I going to be a dirtbag forever?"