Andy Macdonald had a dream from his early days of skating in Massachusetts, and he used that dream as a battering ram to smash through the dramas of his professional career. From penning an ill-received letter, being shunned, and living in roach-infested apartments to being exalted in front of millions, giving international interviews, and owning a house worth close to half-a-million dollars. He wished upon a star and made damn sure it came true.
It all started with a letter. As a seventeen-year-old high school senior in Newton, Massachusetts, Andy Macdonald drafted a letter explaining his future plans. “I wrote a form letter to all the members of my family,” Andy says. “It said, here’s what I’ve been doing, this is what I’m going to do. It’s ’92, I’m graduating next year, I’m going to work at Woodward skate camp, and then I’m going to move to California.” He wrote the letter in a vague, sarcastic tone (as is his sense of humor–easy to misinterpret), and it could have read like he planned to travel across the country to conquer the California skateboarding pros. Known to write things such as “Andy Macdonald, the skateboarder extraordinaire you all know and love,” the letter was what an enthusiastic kid would tell his parents as he was being tucked in for bed. He sent copies to family, pro skaters he barely knew, and skateboard companies he wanted to ride for.
It was like a letter from the Unabomber; it exploded all over the skateboard world. Immediately, people were faxed and mailed copies or heard through the grapevine about Andy’s bold proclamations.
“I’ve never even seen it,” Paul Zitzer says. “I’ve heard about it for ages. It’s like Greek mythology: you’ve heard so much about it, you don’t know what’s true.” Zitzer remembers the gist of the infamous letter: “The main thing was how Andy’s coming to California, and everybody had better watch out.”
“It wasn’t all about skateboarding,” Neal Hendrix, who actually read an original, remembers. “It talked about graduating, and his grad party, and his recent contest placings. It wasn’t stuck-up; it was more like, ‘Hey, check me out.’ I couldn’t believe it–I thought it was a joke that somebody did to him, like somebody else wrote the letter and put his name on it.”
Andy mailed Tony Hawk a copy, too. “I just thought it was weird because it seemed personal, for the family, not something he’d send around,” Hawk says. “I didn’t think it would be a detrimental move.”
Chris Miller also received Mac Daddy mail. Andy had stayed at his house previously, so Miller already was aware of his sense of humor. “I just laughed,” Miller says. “I didn’t think it was a big deal.”
Andy’s girlfriend at the time, Rebecca Philman, a transplant from San Diego who’d recently moved to Massachusetts, heard about the seismic reaction to The Letter from friends in San Francisco. “When I read the letter, it sounded normal–it was just him talking about his dream,” Philman says. “I can see how other people see him and hear him, and how they’d take it, but they just don’t understand.”
Andy’s letter did indeed do what it intended: it announced to California that he was coming out. Only, rather than encouraging the welcome mats, it painted a black “X” on his door. He was a leper in Rector pads to most of the skateboard world–the one world he wanted to join more than anything else in his life. He’d unintentionally exiled himself from the club before he even got into town. And the club, to some extent, still doesn’t welcome him. So, he’s made the club, and everything surrounding it, come to him.
Andy Macdonald’s parents divorced the year he was born. Along with his brother Kyle, who’s three years his senior, Andy grew up spending his school year with his mother in Summerville, Massachusetts, and his summers with “Pops”–as he calls his dad–in Ann Arbor, Michigan. Though divorced, his parents continued to be friends.
An active boy with a healthy imagination whliked Star Trek and turned into Condorman shortly after he saw the Disney movie of the same name, he burned off his childhood energy on the soccer team, swim team, basketball team, and in gymnastic class. Close to his brother, Kyle never seemed to mind if Andy tagged along with him and his older friends.
At age eleven, Andy got the skate bug. “I saw a guy riding one of those wide boards at a basketball court,” he recalls. “All I had was a banana board. He let me try it and I thought it was the coolest thing, so I asked for one for Christmas.” His brother had also showed an interest, and shortly after Andy unwrapped a “wide” Variflex under the Christmas tree, Kyle’s friend gave him a used Madrid.
“I’d just skate around town and try to keep up with my brother and his friends. He had friends who were actually into skating–the whole scene; they got magazines and stuff,” Andy remembers. He made friends with skaters, and together they immersed themselves in their new obsession. When Andy and Kyle visited their dad in Ann Arbor, they skated their first ramp, a sketchy backyard halfpipe. They borrowed pads for the first few weeks until they got their own.
Supportive from the get-go, Mr. Macdonald helped them build an eight-foot-high, eight-foot-wide quarterpipe at their mother’s house. Andy quickly established himself as the motivational leader. “He was always the last guy to stop skating,” Joe Roman, a childhood friend, remembers. “There would be snow on the ground; we’d all put skating off for a day, but Andy would be out there shoveling the snow.” They built a four-foot-high jump ramp and tried to jump Mrs. Macdonald’s car. Eventually, the gang carried the quarterpipe three blocks and handed it over Joe’s fence into his backyard. They built an identical quarterpipe, some flatbottom, and Andy Macdonald had his first halfpipe.
Soon after, he began taking the train to Maximus (a skatepark that housed a nine-foot-high vert ramp), entering contests, and traveling to skate spots. Mr. Macdonald chauffeured his sons to various spots during their summer visits–a four-hour drive to a skatepark wasn’t out of the norm. One summer they went all out with the A.K.R. Tour (Andy, Kyle, and Rod–Mr. Macdonald’s name). A., K., and R. traveled up the East Coast for three weeks. Dad videotaped his sons who’d watch themselves to see how they could improve. “I remember being scared to drop in,” Andy recalls. “I actually have a video of me just slamming. My dad filmed it and is going, ‘All right, get back up on the horse, do it again.’”
By age sixteen, Andy garnered some attention through contests and a TV commercial for Fluff (an East Coast sandwich spread consisting of marshmallows and peanut butter).
Kyle moved to San Francisco to go to college, leaving Andy minus a friend and skating partner. He still skated Maximus and began hinting to his parents that after graduation he wanted to move to San Diego and pursue his dream of becoming a pro skateboarder. And it was straight-up dream. Skating was dying, with vert already in the ground under three feet of dirt. Andy was sponsored briefly by Who Skates before they went out of business. He won the 1993 Amateur Finals in vert and placed second in mini-ramp with no sponsor. Vert was deemed “next to useless” by most of the industry, and Andy was not a true street skater in the eyes of sponsors.
During spring break of his senior year, he visited California. He stayed at Chris Miller’s house as well as the Blockhead house. He skated with Kris Markovich (who gave Andy some clothes because he thought Andy’s pants were too tight) and other pros. Even though he definitely had talent, he was still a vert skater, so no major sponsor showed interest.
Back in Massachusetts, Andy was finishing his last year of school, skating, and hanging out with his girlfriend, Rebecca Philman, also a skater. He peppered her with questions about Southern California. Their first “date” consisted of going street skating together. Even though Andy liked Philman, he was always clear about his love life: “It will always be a contest between them his girlfriends and an inanimate object, and they’ll lose.”
going street skating together. Even though Andy liked Philman, he was always clear about his love life: “It will always be a contest between them his girlfriends and an inanimate object, and they’ll lose.”