After graduation his parents had harshly opposing views concerning his future. His mom wanted him to continue his education while his dad encouraged him to follow his dream. “This is my plan,” Mr. Macdonald remembers Andy saying. “I’ll go to San Diego, I’ll get a job, and try to get sponsored.”

For Mother’s Day, Andy presented his mom with a card that was stapled, locked, glued, and sewn shut. It said, “If you can open this card in ten seconds and not rip it, I’ll go to school next year and forget about all this silly skateboard stuff.” Logically speaking, Mrs. Macdonald had the right opinion: skating was at a low, her son had no major sponsor, little money, and few contacts in San Diego. But Andy wasn’t paying attention to logic; he still had a death-grip on his dream, and that dream fueled him for years while he banged his head against the skateboard door until it eventually caved in.

Even though she opposed the move, Mrs. Macdonald gave Andy her 1982 Nissan Sentra to drive across the country in. It had a broken radiator, so he drove the entire way with the heater on full blast, sitting on vinyl seats with bottles of Gatorade beside him. He arrived in Ocean Beach and hooked up with a group of local pool skaters (with whom he still regularly skates) and lived in a variety of crappy apartments. He worked in the blazing sun inside a bulky, fur-covered Shamu costume at Sea World, did low-budget promotion for the infamous Spike and Mike’s Festival of Animation, and finally got a job at a surf/skate shop called The Green Room. With tough times and scare money, Andy’s dream was deflating by the day.

But he hadn’t spent his entire teenage years sustaining the dream to let it go unattended. He kept skating with pros, learning tricks daily – and got nowhere. People were still acutely aware of The Letter. Andy realized that skating ability was only a part of getting sponsored. “I learned the hard way; I thought it was all based on skating ability,” he says. “That’s not it at all. It’s not how good a skater you are, it’s a factor, but not as much as you would think.” He finagled a pass to the Action Sports Retail Expo (where all the skate companies exhibit their goods) and from walked booth to booth passing out a portfolio that included a skating video and a list of accomplishments.

Mike McGill liked what he saw on the trade-show tape and put him on Chapter 7. “I was set up, but it wasn’t really going anywhere,” Andy says. He’d begun to localize the skinny, indoor ramp at the Thruster warehouse ten minutes from his apartment. “The guy who owned it made snowboards and wake boards,” Andy remembers. “He wanted to have a skateboard division and asked me if I’d start and run the whole thing.” Andy could start the company and have a pro model. In 1994, the two started Human skateboards. Andy contributed heavily, but his dream was never to run a company – he wanted to be a pro skater, so he hired a friend to manage Human.

Andy’s salary was well below the poverty line. “When I first turned pro, I didn’t have enough money to pay rent. I was going to contests, and the sponsor wasn’t paying for me to get to the contests. I’d skate hard enough to make the cut, maybe not go for it as hard as I should’ve – I’d skate conservatively, just enough so that I was in the money and had enough to pay for my trip home and the rent.” His first pro contest was the original Vancouver Slam City Jam, where he placed fifth. Thrasher wrote that his father was one of the judges (they shared a last name) – he wasn’t. The next year, Andy placed fifth again in Vancouver. The magazine commented that he never did a trick higher than two feet.

For the first few years of Andy’s pro career he did well in contests, usually placing near the middle or tail end of the top ten; but he was stuck. He actually won a pro street contest before a vert one. But the second X-Games in Newport, Rhode Island changed all that. On TV, viewed by millions, he won the vert contest”When he beat Tony in Newport, I think he gained a great deal of respect in the skateboarding community,” Mr. Macdonald says. “And it boosted Andy’s confidence. He progressed faster than before.”

But Andy felt the pressure the following year. He did amazingly well in the regular contests, placing top-three in almost every one. Then, the reigning champ choked at the X-Games. He failed to even make the cut. Andy had just quit Human and skated the contest sans board sponsor. “I skated horrible,” he remembers. “I bailed the same trick twice. I was disappointed in myself because I let my pop down; he’d come all the way from Michigan to watch.” Mr. Macdonald videotaped the run, and they watched it together, afterward. Andy remembers him being supportive and offering some fatherly advice, “He just said, ‘That’s not the first time it’ll happen.’”

Andy eventually hooked up with Powell, a company he’d wanted to skate for as a kid. Incredibly, until that point, he’d made relatively little money from his major sponsors, except for Airwalk. But now, with a healthy salary from Split, Powell, and Airwalk – not to mention touring money and contest winnings – Andy’s taking his dream to the bank.

At the 1998 X-games Andy won vert.

Walking into Andy’s massive new house in Ocean Beach, California makes you realize he has definitely “made it.” It cost close to half-a-million dollars and he put down a serious 100-grand in cash – most of it earned from contest winnings. It’s three stories, has huge picture windows, wood floors, large rooms decorated with odd furniture, and a large backyard – with a 3,000-dollar, competition-level trampoline. The walls in his room are plastered with skateboard paraphernalia and his living room has plastic, phony TVs and VCRs. (He hates TV with a passion, never watches it, and relies on friends for news updates. He’s never even watched the X-Games on ESPN.) Andy’s had little time to enjoy his house and non-TVs; during the three months following the X-Games, his hectic schedule allowed him to be home for a mere four-and-a-half days.

Even with his incredible house and his accomplishments Andy’s still afraid to slow down and take it easy. Perhaps years of running over obstacles have become such a habit he can’t stop himself. Maybe there’s a lurking fear he’ll lose his dream. But close friends have noticed he’s slowed down … a little bit. “Before, when he’d come back to Massachusetts, he wouldn’t put his skateboard down,” Philman says. “Now, I can see he’s more relaxed; we can actually talk about other things and do other things.”

Andy has even suggested that he and Rebecca might “get a little serious.” The inanimate object is losing some ground.

His dad noted similar changes from the days when he imposed a “no skateboard talk for half an hour” rule, so he wouldn’t go insane on road trips. “I think he’s just as driven as before,” Mr. Macdonald says, “but more relaxed – he knows he’s good. His inner confidence has grown. I think he’s got everything he wanted and said, ‘Good for me.’ But he hasn’t reached his peak and has a lot to learn. He has other interests to pursue that skating gets in the way of.”

“I think he’s mellowed out a bit,” Hendrix says. “I definitely think he’s gotten where he wanted to go – he’s not so aggressive anymore.”

In regard to the cliquey aspect of professional skateboarding – the right clothes and the cool way to talk – Andy has changed very little and continues to keep an arm’s length away from those groups. Whether this can be attributed to his sense of self, or if being vibed by some of the pros earlier forced him to step back as a defense mechanism is hard to tell. It’s probably a mixture of both. “I never tried to fit in with the cliques,” he says defiantly. “I skate pools – no vert pro skates pools. I skate with people who skate purely for the fun and enjoyment. They don’t have aspirations of becoming a pro, or getting free boards, or anything. They pay for all the stuff they get, they love to skateboard – that’s what motivates me, because that’s what 99 percent of the skateboard population does.”

The fact that Andy had a “plan” may be what irks the few skaters who have a problem with him. There are many unwritten laws to being a pro, and being a good skater isn’t the end all. Kids skate, get good, and a company hooks them up – they don’t plan full-scale invasions of California like it was D-Day. Or if they do, they sure as hell won’t admit to it. They definitely won’t write about it, providing documented proof.

He may sometimes break the rules of skating etiquette (he can be a tad overly competitive), but in an age of incredible unprofessionalism, Andy is a professional in the true sense of the word. He skates his best on shitty ramps at demos, he’s nice to kids, and signs autographs for hours on end.

There’s no denying that some people still hold something against him. For example, the MTV skate party is invitation only. Guess who got invited – as an alternate? That’s like having a pick-up game of basketball and not picking Scottie Pippen until the end. Thrasher made an absolutely useless list of the so-called “Ten Most-Hated Skaters,” with Andy on it. Hated? Andy is the farthest thing from an asshole you’ll ever find. His humor sometimes strikes people at odd angles but it’s never malicious. If you know him, even barely, you know he’ll always help you out when you need it. There is even a skater out there who is a racist shitheel, and he doesn’t get treated like Andy has.

People may have a problem with his ease of tricks or their lack of height, but some of his peers have noticed a change. “His skating has gotten stronger, more modern, and technical in the last three years,” Hawk says, explaining how Andy went from the middle of the pack to the top of it. “He makes his tricks look too easy, like he’s not trying – it’s a curse. If someone else did Andy’s run, they’d win hands down.”

“I always thought he was way cooler and nicer than the heat he took,” Miller says. “People are harsh. In skating there isn’t as much room for the individual. It used to not matter if you were Craig Johnson or Neil Blender – there was room for a variety of people. Andy was just being himself when he wrote the letter; he was young and excited about what he was thinking. The good thing about Andy is he is who he is and has a strong sense of himself.”

Regarding his skating career Andy has a single regret: “If I could do it again, I wouldn’t have written the letter.” But, a little later he backtracks and corrects himself with a tinge of Nietzschean philosophy: “Ultimately, it had a positive impact: it made it harder to get where I am.”

Speaking of where Andy is, his crazed schedule forced our last interview to be squeezed into a half-day layover before he jetted off to Europe. We went out to eat, and he gave me a handwritten letter of the people he wanted to thank. I forgot it at his house. He retrieved it and gave me shit. During the meal he commented that he hadn’t sent a letter to his parents since The Letter. “I send e-mails now,” he said. “Nobody reads them but the person you’re sending them to.” At the restaurant, I forgot the letter, and, once again, was scolded when he retrieved it. I dropped him off at the airport, and as Andy heaved his massive skate bag over his shoulder and headed into the terminal, he turned and said, one last time, in a serious tone – almost paranoid, “You’re sure you’ve got that letter, right?”

r all the stuff they get, they love to skateboard – that’s what motivates me, because that’s what 99 percent of the skateboard population does.”

The fact that Andy had a “plan” may be what irks the few skaters who have a problem with him. There are many unwritten laws to being a pro, and being a good skater isn’t the end all. Kids skate, get good, and a company hooks them up – they don’t plan full-scale invasions of California like it was D-Day. Or if they do, they sure as hell won’t admit to it. They definitely won’t write about it, providing documented proof.

He may sometimes break the rules of skating etiquette (he can be a tad overly competitive), but in an age of incredible unprofessionalism, Andy is a professional in the true sense of the word. He skates his best on shitty ramps at demos, he’s nice to kids, and signs autographs for hours on end.

There’s no denying that some people still hold something against him. For example, the MTV skate party is invitation only. Guess who got invited – as an alternate? That’s like having a pick-up game of basketball and not picking Scottie Pippen until the end. Thrasher made an absolutely useless list of the so-called “Ten Most-Hated Skaters,” with Andy on it. Hated? Andy is the farthest thing from an asshole you’ll ever find. His humor sometimes strikes people at odd angles but it’s never malicious. If you know him, even barely, you know he’ll always help you out when you need it. There is even a skater out there who is a racist shitheel, and he doesn’t get treated like Andy has.

People may have a problem with his ease of tricks or their lack of height, but some of his peers have noticed a change. “His skating has gotten stronger, more modern, and technical in the last three years,” Hawk says, explaining how Andy went from the middle of the pack to the top of it. “He makes his tricks look too easy, like he’s not trying – it’s a curse. If someone else did Andy’s run, they’d win hands down.”

“I always thought he was way cooler and nicer than the heat he took,” Miller says. “People are harsh. In skating there isn’t as much room for the individual. It used to not matter if you were Craig Johnson or Neil Blender – there was room for a variety of people. Andy was just being himself when he wrote the letter; he was young and excited about what he was thinking. The good thing about Andy is he is who he is and has a strong sense of himself.”

Regarding his skating career Andy has a single regret: “If I could do it again, I wouldn’t have written the letter.” But, a little later he backtracks and corrects himself with a tinge of Nietzschean philosophy: “Ultimately, it had a positive impact: it made it harder to get where I am.”

Speaking of where Andy is, his crazed schedule forced our last interview to be squeezed into a half-day layover before he jetted off to Europe. We went out to eat, and he gave me a handwritten letter of the people he wanted to thank. I forgot it at his house. He retrieved it and gave me shit. During the meal he commented that he hadn’t sent a letter to his parents since The Letter. “I send e-mails now,” he said. “Nobody reads them but the person you’re sending them to.” At the restaurant, I forgot the letter, and, once again, was scolded when he retrieved it. I dropped him off at the airport, and as Andy heaved his massive skate bag over his shoulder and headed into the terminal, he turned and said, one last time, in a serious tone – almost paranoid, “You’re sure you’ve got that letter, right?”