Skateboarding at 50 years young: Andy Macdonald and his Olympic tilt - “It’s a Hail Mary long shot”

By Chloe Merrell
8 min|
Andy Macdonald at the 2023 Rome World Championships
Picture by Garry Jones Photography

“I can show you interviews, like TV interviews I did when I was 30, and the question was: ‘How long do you think you can keep doing this?' And I honestly answer, maybe 32, 34?” Andy Macdonald recalls with laughter on a February morning from a hotel room in Dubai.

The 50-year-old skateboarding legend, professional since 1994, good friends with Tony Hawk and proud owner of the record for most X Games vert titles, is in the United Arab Emirates to confront a crucial junction in his pursuit of the Paris Olympics.

The Games are not exactly a “dream” for the British American, but a welcome second chance to do what he has loved for the past 30 years.

And the veteran is thriving off it.

“Here I am, 50 years old and still finding a way to have fun and meet new people and skate new places and travel the world,” he continues. “It’s the best experience.”

Just how Macdonald ended up on the cusp of making it to the second phase of the Olympic qualifying process started two years ago when he learned he was technically eligible for a British passport through his Luton-born father.

With that, he realised he could plausibly try out for the British team opening the door to a tilt at the Olympic Games.

It was an exciting idea, and with money no longer coming in from his professional skateboarding status it was an ideal option. But Macdonald first knew he had to clear the decision with his wife. When an understanding was reached that any money spent would be Macdonald’s own and not taken from the family’s savings, they reached an agreement.

Securing his wife's blessing, was the first part of the equation. The second - which Macdonald concedes he still very much has to work on - is adapting to the park format.

The years he spent successfully plying his trade in vert, a discipline of skateboarding that invites riders to tackle near-vertical surfaces like half pipes with the tricks being performed mostly while the skater is airborne, haven’t quite proved as useful as he might have hoped.

“A vert ramp is 14 feet high and the deepest bowls in park skating in the Olympic Park series are nine feet high. So it's like taking everything I know from vert skating and trying to apply it to like, a much smaller, quicker, genre and that is like learning to do it all over again.

“I can do tricks on the very first try every try. And I go to the smaller bowl and it takes me ten, 15 tries to do it once. And it's just maddening, but challenging at the same time,” he continues smiling, revealing the competitor inside.

“So as long as I keep a positive attitude and I'm up for the challenge, that's what I'm learning.”

Watch WST Skateboarding Dubai Park LIVE | Sign up now to get live stream access

Andy Macdonald: Just a 50-year-old having fun

When he is whipping around the park bowl, egged on by the quips of approval from the legions of young skateboarders seeing a legend at work, Macdonald hardly looks as if he is entering his sixth decade.

He insists, that when he’s skating, he also doesn’t feel it.

“Mentally I’m there. I’m a teenager like they are when I’m out there skating,” he says without hesitation. It just takes me longer to heal, that’s all. “We take the same slams, but I’ll just be like, ‘Oh’ for two weeks, and then I’m like, ‘Yeah, let’s go.

“That’s the main thing with being an older skateboarder. And that’s about it. It’s the same level of fun certainly.”

What perhaps does underline his age, if it isn’t his expertise, is the small fact one of his teammates also in the running for Paris 2024 is 37 years younger.

13-year-old Tommy Calvert, who, like Macdonald, lives in the spiritual home of skateboarding in sunny San Diego, often trains alongside the veteran and the two often cross notes.

“I met Tommy when I decided I was going to try and learn how to skate the smaller discipline in skateboarding. And I started going to a place near my house called the California Training Facility. And I met Tommy, who was also going out for the British national team. So we started training together, Tommy was 12 at the time, and I was 49 at the time. And it was neat.

“I mean, in what other sport do you really ever see that happening where where you're competing against, people that are that age disparity? But very much on the same level, you know? Yeah, I have more experience, but he's got more balance,” Macdonald continues chuckling. “So, it's been neat.”

Andy "Mac" having fun at the 2023 WST: Park World Championships in Rome

Picture by Garry Jones Photography

Skateboarding: A truly global sport

Getting to bed himself in the British team and helping support the younger skaters has been one of the highlights of the Olympic qualifying process, Macdonald says.

Just two weeks before Dubai, the squad made a trip to Southern California where the legend hosted them for a training camp. Watching the riders receive the support to pursue their skateboarding dreams has been something, more broadly, he’s been approving of.

Having had a front-row seat to the skateboarding industry, particularly in the 1990s when the sport surged commercially, Macdonald can appreciate the tension between the Olympic dimension of skateboarding and the cultural side.

“Olympic skateboarding is over here,” he gestures to one side.

“It's far away from what some people would call core skateboarding. Where the industry is, the media and the endemic skateboard companies and culture is over here,” he points to another.

“I’ve always been of the mindset that skateboarding needs to be grown. There's a mindset that's like skateboarding came from the streets, in the backyards, and that's where it needs to stay. And I went through this with the development of the X Games. The first explosion in skateboarding in my career was the X Games. I turned pro in 1994. X Games started in 1995. Tony Hawk won the first year. I won the second year he won the third year I won the fourth year. We teamed up for doubles and won doubles for six years straight. And that was like my career. And my career was through, and married to non-endemic companies and sponsorship through television.

“As far as the Olympics is concerned, that's only bringing more of that. And then add to that the national teams that are supporting athletes. There are definitely, athletes today who have support that can make a living skateboarding through either their national teams or through sponsorships. They get through a potential Olympic bid that just wouldn't even be possible, in the endemic skateboarding world. So it's, it's allowing for more athletes to make a living riding their skateboards,” he continues.

“I was on the first pro skateboard tour to Malaysia, for example. And there are some Malaysian skaters with Olympic bids this year.

“It's just been amazing to share skateboarding globally because for the first time now, I mean, it is truly a global sport. There's a Team Nigeria; there are skateboarders from all over. If there's cement there, there's skateboarding there. And when I picked up a skateboard in 1986, that was not the case.”

Paris 2024: a Hail Mary long shot

Back to the subject of his own quest for Olympic glory, it’s clear that for Macdonald, the Games are more the cherry on top of the cake than anything else.

A committed family man, his children - all more grown than some of his British teammates - play on his mind and he justifies his Parisian chase.

Currently sitting in 46th in the Olympic World Skate Rankings, just two spots away from the 44th place cut-off for the next phase of qualification, he knows he has to do better than he has so far if he wants to proceed to the Olympic Qualifying Series. That test will come on Thursday (29 February) but it won’t be a burdensome one.

“If I make it awesome, I get to go continue this journey, and the next one's in China and then Hungary, and, who knows, maybe Paris.” Macdonald muses.

“But it's a Hail Mary long shot and I knew that from the beginning. So if I don't, I get to go home and be with my kids where I kind of should be and feel good about the experiences that I've had.

“It's kind of a win-win, you know, whether I make it or not.”