The Mastermind Behind Dime Glory Challenge’s Insane Obstacles: An Interview with Casey McDonald

The Dime Glory Challenge in Montreal is the annual spectacle where the world’s best skateboarders gather to push their limits, not with points, but with pure, unadulterated audacity. Forget the meticulous scoring systems; this event is about going big, tackling obstacles that seem straight out of a skater’s wildest dream—or perhaps a nightmare. While the spotlight often shines on the skaters like Chima Ferguson, who are defying gravity, it’s crucial to acknowledge the brilliant minds behind the creation of these death-defying ramps. At LongBoards Guide, we believe in giving credit where it’s due, and today, we’re highlighting Casey McDonald, the ramp builder extraordinaire responsible for the Dime Glory Challenge’s insane contraptions.

After some digging, we connected with Casey, a seasoned skater and builder with a rich history in the Canadian skateboarding scene. Despite his low profile, Casey’s work speaks volumes. We pestered him until he agreed to discuss the planning and building process behind the Glory Challenge’s legendary obstacles.

Can you share a bit about your background in building and engineering?

I’m a skater first and foremost. That’s been my life. About 18 years ago, I got into building skateparks. I’m still building parks, both indoors and outdoors. That led to the event scene where I’ve worked on various events in Montreal.

You were a professional skater, weren’t you? Who did you ride for back then?

I used to be a pro for Control Skateboards here in Canada. I went through the pro circuits in the early 2000s. I turned pro in 2000. I also skated for Osiris for a long time and bounced around with a lot of different sponsors. Being a Canadian pro skater was a very different experience than being in the US.

Were you able to make a good living as a pro skater in Canada?

Hell no [laughs]. It was mainly about getting product. A lot of the time, I had to hustle – get stuff, sell stuff, and keep what I needed. But I did get to travel, had my expenses covered, and experienced a lot of the world through contests and skating. It’s a life of passion. Much like skatepark building, it’s a life of passion.

How did you get involved with Dime?

I’ve known Antoine [Asselin] for a long time. We used to skate and compete together. I grew up skating with them all. They started the whole Dime program, which became the company it is today. They did their first Glory Challenge in 2015. I was involved in that one, and I’ve been building for them ever since.

When does the build process for the Dime Glory Challenge begin?

It varies. This year, we began three or four months in advance because the ramps were more complex. We wanted to fine-tune everything perfectly. The company I work for, Stacked, starts much earlier with all the event organizing. Josh Clark, one of the co-founders of Stacked, has been involved since 2015 too. We started building the first test in May and spent the summer fine-tuning, making it better and safer, and trying different things at a local indoor park in Montreal.

Are you involved in the initial idea generation for the obstacles?

Dime and Stacked come up with ideas together. Josh does all the 3D renderings and sends me previews of the challenges. We discuss what’s feasible, what won’t work, and then settle on the ones we want to build. Once that’s done, they hand it to me and say things like, “Make that giant rainbow rail not vibrate when they skate it. Make sure no one gets hurt if they fall.”

Do you think the Dime guys have a few drinks and get high when they come up with these ideas?

[Laughs] I couldn’t tell you. I just wait for the phone call like, “This is what we’re doing.” Cool, let’s do it.

Who is the test crew for these massive obstacles?

Antoine and all the Dime guys test them first. They’re the priority. If they’re happy with everything, that’s a good sign. If I feel like it, I’ll try the obstacles too, but usually only the early stages. Even Josh [Clark], the project manager of the whole event, tries them to make sure everything flows and the angles are right. This way, we can fix what’s not working. Everything has to be flawless, since all of the obstacles have to be moved in and out within 10 minutes during the event.

Were you prepared to make the rainbow rail bigger for the contest? Or was there a point where it became too dangerous?

There’s a point where you have to say enough is enough. From a time perspective, there’s only so much we can do during the event. Also, when someone is doing a 22-foot long, 8-foot high rainbow rail, do we really need to see a bigger one? Our rule with Dime is that we’ll build to the maximum, and then we’ll build two more levels because the skaters who come to the Glory Challenge are just amazing. There’s always someone who will push it. Seeing them go higher and bigger than we thought always makes it a good time. If we hit a point where no one can do the sixth stage, we stop it. But we make sure we’re ready for the next stage. The longest wall ride, Zered was doing it switch. We were like, “What the hell?” These guys are awesome.

What are your tips for skating something as massive as that rainbow rail?

At that point, it’s all about full commitment. No sketchy, half-assed attempts allowed. You can’t question yourself; if you drop in, you have to fully commit. I don’t think I’d want to step to the biggest rail [laughs]. Even putting the last bracket to limit vibrations was a struggle. I had to monkey climb to reach it. It’s huge!

Were the bump-to-bar dimensions this year based on a real one?

We took dimensions from a real bump-to-bar and tweaked it for the course. A normal one is a little bit higher and steeper, but you’re also not coming down a 16-foot roll in to hit it and going 600 mph [laughs]. We had to make a smoother ride-in and enough of a kicker to boost off of it without launching someone 15 feet over it. We also look at who is invited to these things and what they’re going to prefer. For example, with Decenzo coming, we knew he was going to want to skate that.

So who did you have in mind for the bump-to-bar?

Decenzo [laughs]. We knew he was going to destroy it. We built it knowing that he was going to skate it and everyone else would too. It’s a universal obstacle, but we knew that he was going to come with a front three in mind. He claimed it before he even showed up.

Have you considered remaking famous spots, like a Dime LOVE gap?

We did the Josh Kasper gap with the DJ at the bottom, like the one he tried. We actually had a DJ there and everyone was popping tricks over him, so we have done that before. I’m sure everything comes from inspiration, but I couldn’t tell you where some of the stuff comes from [laughs].

So, no Leap of Faith remake?

Yeah, and then expect all the skaters to start jumping down that? You could mimic it or make a smaller version, but something that’s actually sized where maybe only one person could do it isn’t going to work out.

I guess the downside is that if someone does try it, they’re going to get hurt.

That’s the risk, so I spend a lot of time fine-tuning, sanding, and making things as flawless as possible. I’m sending fellow skaters over these things, so I do everything I can to make them as safe as possible. But you also have to realize that anything can happen.

Has anyone ever stepped to something that you knew was too dangerous?

This stuff is big, but we also bring in talented skaters who know their limits. They know when to stop. They’re professionals, and they’ll chill when they see that they could potentially get hurt. Everything we do has to be big. We start small so everyone can skate, then it slowly grows until it’s the most ridiculous thing. It’s almost a Guinness World Record type of thing.

It feels like WWF meets Guinness Book of World Records.

Yeah. It’s a show. Some people call it a contest, but it’s a skateboard show. It’s the greatest skateboard show on Earth [laughs]. Like with the game of SKATE where they had a montage of Wade Desarmo coming down in a helicopter and driving a Lambo. It’s a show where the best skateboarders perform and destroy these things.

What haven’t you done? I guess there hasn’t been a manny challenge yet. Could you see something like that?

The point of the obstacles is usually focused on one incredible trick. It’s about allowing skaters to see their favorites do crazy tricks, but it’s also not to get too complex so that the average person watching can also be stoked and understand what’s happening. For example, when Zered did a switch drop-in, every skater in the room was in awe, but the average person was like, “Eh…” So, if you get too technical, the average person won’t understand.

How much does one of those rainbow rails cost?

Some of that stuff, I don’t inquire about. I focus on the build. I let them do what they need to do, and I do what I need to do. I tell them about the materials, but I just let them figure out the costs.

How much would you say the whole show costs to produce? $1 million?

I couldn’t tell you.

Just fart if it’s over $1 million.

[Laughs] I couldn’t tell you. I know the price of wood was triple this year, but when it comes to containers, bleachers, venues, and all of that, I have no idea. Even the downhill rail needed a permit because the entire road had to be shut down. It was supposed to be dry but as soon as we realized it was going to rain, we were like, “Dope. Let’s just Pat Duffy this thing. Let’s put it up just to see if anyone would skate it.” And people started jumping on it! They were sliding everywhere, and you could see the water kick up behind them. Just surviving the hill was a game in itself. The water was flowing down the hill like a river.

The Dime Glory Challenge is more than a contest; it’s a celebration of skateboarding at its most creative and daring. And behind every jaw-dropping moment is the work of Casey McDonald and his team, ensuring that the skate world has a stage for the extraordinary.


Interview by: Ian Michna
Photos by: Casey McDonald, Dan Mathieu, Josh Clark
Check out Casey’s brand La Vie Skateboards here

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LongboardsGuide Team

Hi guys! We are LongboardsGuide team, welcome to our blog. We are here to help you choose the right gear to ride safely, together with Tom creating helpful tutorials and guides for beginners. Everyday I try to share my knowledge about it with all of you.