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Andy MacDonald – the Mac Daddy! | Retro Rippers

Andy MacDonald is a really interesting character in skateboarding. He doesn’t really fit in with most pro skaters. He’s a really hard-working professional skateboarder in every sense of the word. In the intro to his book, Tony Hawk makes an interesting point. He basically says that everyone wants their pro skaters to be amazing at skating, but they don’t want them to try. Meanwhile, Andy trains and drills tricks to keep them consistent. That’s not weird when talking about a regular sport, but it makes you a weirdo in skateboarding. But Andy is actually kind of a weirdo in quite a few ways.

He grew up around Boston and spent his summers in Michigan with his dad. He was one of the first skaters in the area with his brother and a few of his friends. They built a lot of homemade ramps and stuff. From an early age, Andy was completely convinced that he was going to eventually become a pro skater. It was his only dream. He didn’t do great in school and even got held back once. He never thought about going to college or training for any kind of career. He just took whatever jobs he had to to get by.

Luckily, his parents were supportive, helping him get to amateur contests and stuff like that when he was still in school. But his plan, as soon as he graduated high school, was to go straight to California and pursue skateboarding full time. But he had to take some jobs as a dishwasher somewhere and he worked at Woodward camp too.

He finally had enough, and he was ready to leave. But before he did, he wrote… The Letter. This is something that followed him around for years, and people still bring it up. So I have to cover it. Before he moved to California, he wrote a letter talking about how you better watch out because he’s going to take over. This is his first impression on most of the skate industry. He had a mention in Transworld once in a contest article, but nobody really knew who he was. Here’s his story:

“It was full of the same dry humor that even today people have a hard time understanding. I wrote and mailed out copies of the letter without giving it too much thought. I even sent it to a few skaters in California that I didn’t know very well. I just figured it was a good way to let them know i was going to be in town. My family knew me and understood where I was coming from when I wrote things like, ‘Andy MacDonald, the skateboarder extraordinaire you all know and love.’ But remarks like this were completely misunderstood by people in the skateboarding community. Taken literally, it sounded like I was some conceited jerk telling everyone, ‘Watch out! I’m coming to California to take over!’ To them, the letter seemed so unbelievably weird that it was faxed out across the skate industry as a joke. Every team manager and bigwig in the business got to laugh at my little letter. I had become a laughingstock before I even left Boston.”

I tried really hard to track down a copy of this letter. It got sent all around and it’s a completely infamous story about his life. But I have never seen quotes or a scan from it. And I wish I could, because he said it was full of Teenage Mutant Ninja Turtles style 90s slang.

Onscreen -Paul Zitzer says “It’s like Greek mythology: you’ve heard so much about it, you don’t know what’s true. The main thing was how Andy’s coming to California, and everybody had better watch out.”

So he basically sabotaged himself before he even went to California, but he had a lot of other stuff working against him. He was really clean cut, not into parties and drinking and stuff like that. He was really focused on putting in practice time, and the way he dressed was too dorky. People didn’t like his helmet and stuff like that. Although he was probably the best dressed person there. When he finally got to San Diego, someone he knew got him a XXL shirt and size 40 pants to wear so he would fit in with everyone else. That probably helped his cred even though it looked much worse in retrospect.

Let’s take a little break and take a look at Andy Mac’s book! I picked this up from the library, but I had to order it from another branch and wait a month for it to come in. So I was really hoping that there would be some great information in here that was worth waiting for.

What did I learn? Not much that was useful. If you want a really deep dive into Andy’s elementary school life, then you’re in luck. He tells a lot of stories about how he stood up to a bully without violence because of his studies into the teachings of Ghandi – in second grade.

About a third of the way through the book, he finally starts skating. He talks about how he stole plywood to build a ramp, and it was such a huge regret. He also talks about turning down marijuana because he got a contact high on accident once and it made him skate worse, so he says he doesn’t smoke ‘dope’. His word.

The whole book is written like it’s for 8th graders or something. But it also comes across really arrogant. Not so much in his actual attitude, although there’s a lot of that too. But it’s just the way that it’s written as if there are deep lessons in everything that’s happened in his life. Almost like you’re studying the life of a huge historical figure like Abraham Lincoln, or Moses or something. But he’s just a dude who really likes skateboarding who got good at it and won contests and got sponsored by everybody like and stuff.

But that just seems to be his personality. He talks about how he moved to California while his girlfriend was still in school. He wrote her love letters once or twice a day. But when he saw her again, she didn’t know they were still a couple because he only wrote about himself.

So I pulled a couple of quotes from the book for the video. But don’t bother trying to pick it up, even for free from the library.

OK, back to the story. It’s about 1992. He’s a weird outsider already, and…. He skates vert. Vert was about as dead as it could get. You’d have a video part here and there from a big name, but it wasn’t growing. Nobody was looking to sponsor new vert skaters.

So Andy gets to California and skates his heart out, but it wasn’t really going anywhere for him. He was working crappy jobs, sleeping on the floor, stealing food and just wondering if he made the right move.

But he had a plan – win the NSA vert competition. Back in the early 90s, NSA contests were huge. If you won, your sponsor was basically obligated to turn you pro. Or, if you didn’t have a sponsor, you’d get one, guaranteed. So this is what Andy planned on doing. But here’s his story:

“In ‘92, I had won second place in vert and second in miniramp, but I still had no sponsors. Maybe this year it would be different. I won first place in vert and second in miniramp. In years past that would have gotten me a sponsor on the spot, but not anymore. Skateboarding was still in a slump. Even the NSA went out of business after that competition, and because vert skating especially was dead, not many companies wanted to crank out boards that weren’t going to sell.”

That sucks. That’s like growing up with a passion for working at a newspaper, only to graduate right when they went out of business.

But he stuck with it, and just kept working. He had a plan. He went to a trade show and handed out resumes. Here’s the story:

“I put together a portfolio of my skateboarding experience. I included a list of all the contests I’d entered, and I added magazine photos and stories that included my name. Then I walked around the Action Sports Retailer trade show to give out copies to all the companies I thought I’d like to ride for.”

To hear him tell it, this is where the aftermath for his letter really kicked in. People already thought he was weird, and now he comes up to you with a resume and clippings from Thrasher?

In a way, this plan made a lot of sense. It’s not about your skating so much as who you know. And the people he knew didn’t like him. He did manage to get a small sponsor though. Chapter 7 skateboards. It didn’t really go anywhere though.

Later he started working with a company called Thruster and helped launch a brand called Human. He worked closely with the company, but it didn’t go great. They were missing paychecks and they even forgot to buy him a plane ticket to a contest overseas and he missed it. But he did start traveling a lot and hitting a lot of contests whenever he could.

“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.”

In his first pro contest, Slam City Jam, he placed fifth. Thrasher reported that his father was one of the judges. But he wasn’t. He just had the same last name and Thrasher made it up. He placed fifth again the next year and Thrasher complained that he didn’t get any higher than 2 feet.

But Andy’s contest performance was really calculated in these early days. All he cared about was getting a high enough placement that he got a little prize money. Fifth was good enough to keep his bank balance from hitting zero, and he needed it. He couldn’t risk trying going too big and bailing. So he did his consistent stuff low and collected a minor check.

He got second in vert in the first X Games in 1995. But that wasn’t enough to win him any respect in the skate industry. In April 1996, Thrasher put Andy on a list of the top 10 most hated skaters. This is what they said,

“6. Andy MacDonald. The Mac Daddy, as he calls himself, makes it a point to out-train and out-do everyone else at a given contest. He will bust out the devil sticks, juggle and alley-oop body varial anything to get the attention that his parents think he deserves. He even sends newsletters to his sponsors keeping them abreast of the tricks he has learned and the friends he has made.”

Andy said they later gave him the opportunity to rebut what they’ve said about him before, and they basically just told him he skates too much. He joked that he runs 5 miles a day and drinks a glass of raw eggs every morning, and they took that quote and used it as a caption. Not only was he hated by the industry, but apparently didn’t judge well either. Tony Hawk said,

“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.”

The next year, he actually beat Hawk and won gold in the X Games. But the media’s attention was on the upset and about Hawk, and he still didn’t get a ton of respect.

But as far as sponsors go, he was finally taken care of. He got on Powell, which had been his dream since back in the Bones Brigade days. But he also started to take on lots of non-skating sponsors, which is kind of weird. Over the years, he worked with SoBe drinks, LEGO,, and all kinds of other corporate sponsors. He gets called a sell-out a lot because of stuff like that. You can kind of imagine why he does this stuff though. After years of struggling and having to steal food and stuff, it’s tough to turn down a paycheck. And this is what he has to say about it:

“But I know that as long as I’m being true to what I believe in, that’s all that really matters. I pride myself on making sure that the sponsors I choose give something back to the sport that has given me so much. For example, before I signed with LEGO, I convinced them to sponsor the California Amateur Skateboard League. Sonja Catalano, the woman who runs the CASL, came up to me at an event and gave me a big hug. ‘Thank you so much,’ she said. ‘LEGO’s been the best sponsor. We’ve had more success this year than ever.’ Corporate sponsors are the reason many more of us can make a living doing something we love. Compared to any other sport, pro skateboarders are still just getting started. If I had wanted to be rich, I would’ve played golf.”

I don’t think he plays golf at a professional level, but alright. I can see where he’s coming from to a degree. If the X Games was ONLY sponsored by skate brands instead of Rite Guard and stuff, then that money is coming from you, as the skater who buys those products being advertised. So in a way, I can get what he’s saying. But it always feels weird to see a dude shredding a pool with a sticker for on his board, you know? Getting those brands to sponsor events is fine, but taking a paycheck from them when their product has nothing to do with skateboarding feels weird to me. I get offers from weird Chinese companies all the time who want me to review stuff. But it’s never skateboarding related – makeup, cheap graphics cards and stuff like that. At some point, you have to say no to stuff that isn’t going to help anyone.

Over the next few years, Andy’s career really started to blow up. In 1998, he won the “Best Overall Skater” award in the “Readers Poll” of Transworld. And although it’s a readers poll, the skaters were nominated by pro skaters, so he did get some kind of respect finally.

But I have to show you something from an interview he did with Transworld after his win. Being the best ‘overall’ skater, the interview is mostly about how important it is to be well rounded. Check out this part:

“Do you ever get bummed that there are guys who only skate one type of thing and make successful careers out of it?
No, because they’re pushing that envelope. I don’t get mad at them, I get bummed for them. For example, Eric Koston is an amazing street skater, pushing the envelope as far as street skate goes, but I know for a fact he can kill a vert ramp. So, I feel sad that Eric doesn’t spend time on vert coming up with amazing stuff. Tom Penny could kill a vert ramp, too–you know he could! I just think they have more to offer.”

Call me crazy, but it sounds like he pities Koston and Penny. Penny could 540 on vert, and it might have been interesting to see how he pushed vert if he focused on it… but he didn’t want to. Implying that he’s missing out in life because of how he skates comes across a little elitist and weird. Like he’s putting his way above everybody else. I’ve seen interviews with people who know Andy and they say that he’s the nicest guy ever. So I don’t know if he actually thinks he’s better than everybody, or if he just puts his foot in his mouth a lot. Hard to say. I’ve never met him.

“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. -Transworld, 1999”

In 1999, he gave an anti-drug speech at the White House, and he was on Jay Leno around that time too.

In 2000, he got his own video game, which I reviewed before. MTV Sports Skateboarding featuring Andy MacDonald. I reviewed this one a while back. It’s not good. But it is very interesting. He worked with MTV on it, and made it to the cover despite other big names being in the game, like Danny Way, Stevie Williams, Josh Kalis, Rob Dyrdek. But just a year before this, this happened:

“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.”

That’s from his pro spotlight in Transworld from 99. I don’t know much about how that event, but it says something.

Over the next few years, Andy got involved in some other businesses, like a new kind of pogo stick that he helped work on. But his biggest new business venture was Andy Mac Skateboards, which he made with Powell. This is what it looked like. The deck was his actual pro model that he used, and it came with generic quality trucks and wheels. The complete was about 60 bucks, and it was designed to be sold in department stores. I think I remember seeing one of these in Sam’s Club when I was a teenager. It was supposed to be good enough for anybody, but it’s also a good basis to upgrade from. Start with one of these, then you can always upgrade the trucks and stuff as you go. But it’ll be good for a long time as it is. And it supposedly came with an instructional DVD to help you get started.

I remember thinking that these were a really good idea when they came out, but of course it was controversial because the money was going to a department store and keeping kids out of a skate shop.

In any case, the brand only lasted for a few years.

So that takes us up to the mid 2000s, but what has he been up to since then? He has still been competing in as many contests as he can. His website said he’s up to 23 medals at this point.

In 2008, he made news getting involved in the Fresh Air Fund, which is a group that helps provide free summer vacations to kids in New York from low income families. He won their “American Hero” award. And he spends time helping teach kids to skate. Also, in classic Andy Mac style, he got his shoe sponsor, Airwalk, to provide a special edition customizable shoe. The profits from that were donated to the Fresh Air Fund.

A little later, around 2012 – I’m not 100% sure – he partnered with and started selling his new brand, Positiv skateboards. His website has this to say:

“Positiv Skateboards is Andy’s brainchild, and brings to focus the many positive aspects of skateboarding and its top skaters.”

From the pictures I found online, it seems like it’s very similar to Andy Mac skateboards, where it’s a complete with branded wheels and trucks. I don’t know too much about this brand because most of the reviews out there are from parents who bought it for their kids or from beginners or toy reviewers and stuff like that. But I’m sure they were fine. This brand only seemed to last until about 2015.

According to his website, Positiv is still his sponsor. I tried to look at his board on Instagram to see what he’s riding, and I learned a few things. He’s heavily involved with, posting lots of ads for them. But he also posts a lot of sick skating. He’s recently been experimenting with body varial grinds, which is cool to see. This stuff reminded me how much I actually love Andy’s skating.

But as far as I can tell, he actually doesn’t have a deck sponsor at the moment. It looks like he might be on a Powell flight deck in this video, but it’s hard to tell. It would make sense. But he’s very direct about his sponsors, and he tags them in everything.

Right now, it looks like it’s Patagonia, Bern Unlimited,, Theeve Trucks, 187 Killer Pads, Clif Bar and Randoms Hardware. And he’s still skating harder than ever.
You know, say what you will about Andy and his sponsorship stuff, but it always seems like he does try to give back, and that he has legitimately good intentions for what he does.

2 thoughts on “Andy MacDonald – the Mac Daddy! | Retro Rippers

  1. hey rad you should do a video in jake phelps like that one time you talked about him

  2. I just saw him in instagram clip riding a Powell flight board.

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