Words and photos by Eric Deakin
The 10th annual Dime Glory Challenge was the biggest yet. A long weekend’s worth of shenanigans included a rambunctious block party, some soggy street spectacles, all leading up to an extravagant showdown at Montreal’s IGA Stadium.
A brainchild of MTL’s very own, Dime, and the skate shoe giant, Vans; The Dime Glory Challenge (DGC) regularly recruits some of the hottest names in skateboarding to run the gauntlet and show off their abilities through a handful of unique trials.
Pros and Joes alike flocked to the island from near and far to attend and celebrate a decade of the ballistic battle. Personally, I bought my ticket on a whim for $12 USD, and was fortunate to find myself in the mix.
These are some perspectives from the sidelines.
True Anti Heroes, Victor “Doobie” Pellegrin and Petar “Stewie” Stantchev repping hard for the EU. Congrats to Petar, a new addition and good fit for Team 18.
What better way to spend the first day? Travelers came and went as the session tapered, breaking off to Raymond-Préfontaine skatepark or perhaps some dinner reservations. I returned to my hostel, just in time for a spontaneous, golden-hour group activity trip up to Saint Joseph’s Oratory of Mount Royal.
That’s Deandre “Lil Dre” Thebpanya, diplomat of the Yay Area and Girl Skateboard’s latest pro. On the come up for some time, Dre now boasts a catchy Hip Hop album, two signature Adidas colorways and two pro models decks under Caroll’s camp.
Headlined by Darude, the legendary Finnish DJ known for “Sandstorm”; the hit lead single of his 2000 debut album Before the Storm. Considering what was in store for the weekend, it was only right. “Sandstorm” ensues.
Back at Peace Park, but this was no stumble-upon situation. It was the first scrimmage of DGC weekend and after a morning’s worth of rain fell over the city, there was work to be done.
Place was packed, but crowd control made sure there was room to broom. It had to be done, the show must go on. Anybody bring a towel?
Thankfully, both the Sun and the crew were moving diligently in the drying efforts. That includes Big Sexy, a handsome chunk of talented skateboarder and a pillar of the Dime community; He’s not afraid to get his hands dirty, either.
Eventually, the main ledge dried up and the challenge began. As the masses moved in and claimed the best seats in the Park, I filtered out and watched from afar, noticing some familiar faces on Rue Saint-Dominique.
There are a handful of skateboarders in this world that you just can’t help but gravitate towards when you see them in person.
Ryan Sheckler is one of them. Many of us grew up skateboarding, watching him grow up skateboarding, and through his experience he remains a legend to this day. I’m grateful I met him; Sheckler is a true gem and has long solidified his name in the game.
Ishod Wair is another magnetic character; A down to Earth, friendly fellow, I caught him outside the dépanneur (French for convenience store) chatting it up with some Euro homies. We were posted for a cool minute, shooting the breeze and chatting about family, photography, and BMW E30’s as grom after grom approached him for a photo. Cheers, Ishod.
And of course, the newest addition to the Dime family, The Boss. Andrew Reynolds has secured his spot as one of my all time favorite skateboarders, and takes it further by continuing to push those leading values onto the younger generations.
The grinds and slides were long and buttery and the vibes were high. But word on the street was that the big wigs were headed up the block to the infamous Av. de l’Hôtel-de-Ville, aka Challenge Hill. Shit just got real…
Stewie got speed.
Before long, dusk fell over Challenge Hill. Most contestants quickly bit the bullet and made the most of the dwindling light; Viral descents such as Alexis Lacroix’s Valdez tribute and Madars Apse’s handstand bomb. Through the shadows, however, a handful of brave souls opted to hop the handrail, landing right in the crust and barrelling straight to glory.
Dusk led to darkness and it was time to call it. I queried for the nearest convenience store and on the way back, ran into the people’s champ himself, Charles Léon. Charles sent it down the hill twice and ended up with not only severe road rash, but also an unforgettable attitude and overall performance.
Let the games begin!
First up, the big bank challenge. It started as a handful of stairs and a short down rail into the bank, and it grew into a bunch of stairs, with a giant down rail, and a super long flat bottom. Not for the faint of heart, but I’m pretty sure Jamie Foy did the hard part first try.
Can you spot your favorite skateboarder? The lineup was truly stacked.
After an intermission of construction by the hardworking hardhat team, the next event was the pyramid challenge. This one started as an innocent, bank-flat-bank pyramid, but then the flatbottom became a trapdoor. Through the smoke, a sarcophagus was revealed (supposedly that of Joe Valdez?…) which grew taller and taller as contestants tried their luck over it.
Another intermission of construction, made possible by DeWalt, and before you know it, everyone’s throwing bright yellow dodgeballs. It helped to break up the tension.
Wrapping up shortly after, the 2025 Dime Glory Challenge had come to a close. Many scrambled for the fabled Big Sexy afterparty at Apt. 200, where Lil Dre and Ryan Sheckler each took home MVP and a $1M Canadian prize.
Personally, I was exhausted after the big day, but was able to stick around town for a bit and get some exploring in. Montreal is a beautiful, forward city, some claim the best in North America. It’s home to a healthy skateboard scene and has helped to grow the Dime Glory Challenge into what it is today, a sight to behold, to say the least. Big thanks to everyone involved. Here’s to another decade.