We witnessed total skateboarding carnage

Mainstream skateboarding contests are usually pretty pretentious affairs: a bunch of pseudo-celebrity skaters going through the motions of timed runs they’ve rehearsed a million times in front of a bunch of TV cameras, nasal commentators and judges critiquing their every calculated move. And now, skateboarding is officially a sport in the Olympics, the original jock contest. One might wonder, is there any hope for an actually legit skateboarding tournament, one testing super speed, cat-like agility, inner strength and warrior gladiatorship?

Enter the Dime Glory Challenge, an annual skateboarding party thrown by Montreal’s premiere skate crew Dime and supported by Vans, an event that smashes the cyborg contest into a million tiny pieces and shotguns a beer on it. There are no timed runs or trophies, only homies, fun vibes and some really ill-advised, goofy, ridiculous challenges that test skaters’ abilities in more than just putting together a string of spotless, boringly executed tricks. This year included flipping into a vast foam pit, grinding a mythical sword and duelling in a brutal gladiator challenge.

“It’s kind of like an anti-contest, pretty much,” Dime co-founder and Glory Challenge organizer Phil Lavoie told me before the event.

“We had this idea years ago. I went to a skate contest and I thought it was so fucking wack. Like, you get there, it’s the most competitive atmosphere and people are stressing trying to do their best tricks. Like, fucking kooks everywhere, trying to skate their hardest, and it’s just wack. And it’s not even the coolest guy would win — it’s the guy who had the most perfect robotic run. After going to that contest, I was like, ‘Okay, let’s make a contest that’s exactly not that.’”

I went to the inaugural Dime Glory Challenge last year, thrown in a pop-up skatepark in a warehouse by the St. Lawrence River, and I got to see Dime’s vision of a fun-first contest come to brilliant fruition. I went into this year’s with high hopes and found kinship with a fellow skater before even leaving Crémazie metro — a dude in overalls was doing no complys and skating around right on the platform. We skated off together and ending up skitching half a mile on the back of another skater’s pick-up truck who was also heading to the challenge.

This year’s showdown was at le Taz indoor skatepark, but the park itself was barricaded off. The Dime crew opted to construct their own course in Taz’s roulodôme space. As we rolled up, I saw throngs of skaters and girls in crop tops lounging around outside, with a Projet 45 BBQ tent serving up burgers, hot dogs, veggies and beers. My new friend and I played a game of flatground SKATE while waiting for the games to begin, and then finally the garage door entrance rolled up and the crowd overflowed into the park, signaling the dawn of the madness.

The set-up inside was a massive roll-in ramp at one end, a waxed up ledge and a bump-to-fence in the middle and a set of quarterpipes on the other side, which the invited skaters were warming up on. This year’s line-up included legends like Frank Gerwer, PLG and Dustin Dollin, along with young guns like Wes Kremer, Evan Smith and Scott Decenzo.

“The skate world is a small world. Most of the people we knew, but some of the people we just hit up. We send them the challenges — usually they find it pretty funny, so they’re down,” Lavoie said.

“This year I’m really hyped on the line-up. I could never expect Frank Gerwer or Peter Hewitt to come, that’s the craziest thing to me. I’m still overwhelmed with that, these pros coming to our contest and doing our funny shit. Pretty happy about that.”

Speed challenge — Dime Glory Challenge

After the warm-up sesh, the DJ heralded the kickoff of the speed challenge by blasting the 2001 techno dance single “Sandstorm.” The rules were simple: roll in on one side of the park and pick up as much speed as possible, then try to land the best trick on flatground while blazing Mach 5 across the slick concrete. Extra pushes encouraged, speed shades mandatory. Landing on a flipping skateboard while hurtling at breakneck speeds is like trying to shoot a bullet out of the air with another bullet, or like trying to defuse a bus bomb on a highway. I knew from last year that there would be a lot of collisions and dudes eating shit, sliding a good 20 feet before their broken carcasses settled to a stop.

Being the first challenge of the day, all the skaters were revving to go and the crowd was non-stop cheering over the absurd techno beats. Canada’s own Morgan Smith pulled off a nollie backside heelflip and switch frontside heelflip, and Dime’s Antoine Asselin, the steeziest skater there in my opinion, executed a textbook nollie big-heelflip with flair.

Wes Kremer landed a frontside flip and inward heelflip, and Evan Smith was going for it like a champ with a switch bigflip and double flip sex change but couldn’t ride away from either. The polished floor became a veritable slip ‘n’ slide of sweat by the end.

Frank Gerwer, the 41-year-old Anti-Hero pro, shot off a nollie kickflip at high velocity and then launched himself off the corresponding quarterpipe into the crowd, then straight up left the building. He won and took home $25K for his efforts.

Foam pit challenge — Dime Glory Challenge

After the speedstorm, the Dime crew rolled out the colossal foam pit, which the announcers claimed were full of dirty syringes for the skaters’ pleasure, a real cesspool of filth for them to dive into.

Anyone familiar with the Red Dragons, Vancouver’s heavy-hitting skate squad, knows of Rob “Sluggo” Boyce and his vert-meets-acrobatics style. Sluggo is a gymnast, breakdancer, stuntman, snowboarder and skateboarder—basically an adventure sports Renaissance man. Everyone was hyped to see him throw down in the pit and he knew it—he posed and flexed on top of the roll-in like a god on Mount Olympus, then drove the crowd into a frenzy by tearing off his white tee like a blonde Canadian Hulk. Sluggo threw a cork 540 and a switch backflip into the foam pit with “Backstreet’s Back” and “Danger Zone” as the soundtrack for his air show. Everyone else threw in various spins, flips and grabs and Dime’s own Alexis Lacroix closed out the challenge by hucking himself into the pit whilst casually strumming an acoustic guitar. Not sure if that would fly in the Olympics.

Gangster challenge — Dime Glory Challenge

This challenge was all about hip hop, Hennessy, blunts, shoulder steez, guns, gang gestures and flow. Lavoie told me this challenge was inspired by Wade Desarmo, the skateboarding World Champion, for his extra buttery and relaxed style. The only obstacles for this challenge were the ledge and the bump-to-fence.

Antoine Asselin has an organically thuggish style anyway, so as he threw down kickflip indy grab, frontside 360, varial flip and bigflip over the bump-to-fence with photo finishes, I knew he was a shoo-in for the win. Evan Smith pulled off a janky switch frontside 360 heelflip, which would demolish any best trick contest, but this challenge was all about keeping it G, and Biggie would not approve of toe drags upon landing. Bobby Dekeyzer dropped a mind-warping pop shove it revert right at the buzzer, a trick that has roots with the impeccably styled OG dirty ghetto kid Stevie Williams. Antoine and Bobby D brought home the bacon as true gangsters.

Valdez challenge — Dime Glory Challenge

Next up was the Valdez Challenge, featuring a collection of extra-narrow obstacles based on pro skater Joe Valdez’s famous skinny drop-in in Thrasher magazine’s 2001 video “Timebomb.” Lavoie told me that he and Antoine had worshipped Valdez because of that video, so when they ran into him during a skate trip to San Francisco, they invited him out to Montreal to help host the challenge named in his honour.

“He’s the best at skinny drop-ins, riding on anything that’s skinny and anything that’s life-threatening. He’s fucking sick. He’s probably the guy who’s risked his life the most for skateboarding, and he’s still alive, so, respect,” Lavoie said.

The challenge involved clearing an ever-widening flat-to-flat gap on super slender boxes that provided only a few inches worth of margin for error, then also grinding a flatbar and riding away on another skinny box at the end, just to up the stakes further. In “Timebomb,” Valdez threw his hands above his head in a praying gesture before doing his tightrope-esque skate, and that became the symbol of this event, with an entire sea of people throwing up the Valdez prayer sign as skaters approached the gap with speed. Alexis stuck a hippie leap from one board to another waiting on the other box, a feat he also did at last year’s challenge.

As skaters ollied it with ease at first, the announcers called to “make it more Valdez” and Joe himself would come out and measure how much wider they made the gap. It became so wide that Wes Kremer, Thrasher 2014 Skater of the Year, actually didn’t clear it at one point and hung up and completely ate shit, slamming his head and sliding a good 10 feet down and off the box. It was Evan Smith who ended up setting the jaw-dropping “world record” of 14 ½ feet, sailing across the boxes without skipping a beat and throwing back his unruly mane with a big trademark grin.

World championship game of SKATE

This was the most hyped event of the day: the defending world champ Wade Desarmo versus the Wild Card and tornado spin aficionado Jamal Smith. They each posted diss videos to each other the week prior, with Jamal hilariously ranting and calling out Wade’s hair, gear, jewellery and foot stance, all in the middle of a busy Montreal street. Wade responded with an aloof video of him playing golf, “reaping the rewards” of being the world champ and pretending not to know who Jamal is, ending it with one of Jamal’s signature tricks, a fakie biggerspin.

After an extended delay that hyped the anticipation to pre-iPhone-release levels, the contenders emerged like heavyweight boxers from their corners, sporting silk robes and glaring at each other from opposite ends of the park, with water bottles and towels set up at their disposal.

They arm-wrestled to see who would go first, with Wade taking it. But his advantage didn’t last long as he immediately beefed a frontside shove it, which Jamal then executed flawlessly right back in his face on the offensive. Jamal was able to throw down fakie and nollie biggerspins which got Wade letters, but his nerves must’ve gotten to him as he bailed on four basic tricks in a row, getting him to SKAT. Wade threw a backside flip as the final nail in his coffin. Once the game was over, they both broke character and bro’ed down, with Jamal congratulating his previous nemesis on the $100K victory.

Sword challenge — Dime Glory Challenge

Like last year’s grisly guillotine set-up, this villainous, bloodstained weapon forged in the depths of Hell was the craziest obstacle of the day. Only boardslides were allowed on it to maximize the sack factor (smashing your crotch on the rail), and the announcers bragged how they were giving out free castrations for this event.

All the skaters put their children on the line and boardslid across the sword of doom, but surprise! Professional skateboarders don’t exactly go out looking to get sacked and everyone either landed their boardslides or expertly bailed away from the bleeding edge of the sword. The crowd grew restless. Were we going to see a sack or not? We were all rooting for the skaters, but for a second there, the crowd was more like a bloodthirsty mob, foaming at the mouth to see some testicle devastation.

In what was one of the funniest moments of the contest, Torontonian skater Lee Yankou slowly rolled up to the rail and then threw himself on his sword (literally) with a pathetic pity-sack, then climbed down with a shrug and skated off. With that dumb little move, he earned $15K. I honestly considered shoving my socks into my pants as a cushion and jumping up and sacrificing deez nuts for the cash, but Yankou actually delivered.

Evan Smith and Scott Decenzo duked it out with competing boardslides as the sword surged higher and higher, and the final height was a whopping 5’9” up, or one Frank Gerwer-tall. Smith couldn’t close the deal on it but he had the crowd eating out of his hand as he soared up onto that devil’s toy and slid across it to victory, with his highest boardslide hitting the 5’3” level.

Kasper challenge — Dime Glory Challenge

The Kasper Challenge was a hefty drop over a DJ that was inspired by Josh Kasper’s iconic ollie attempt in the 1999 Blind video “The Storm.” One brave soul posted up under the drop to scratch beats as dudes started hucking themselves over him — thankfully, he didn’t take any boards to the head. Morgan Smith laid down a switch heelflip over it effortlessly and took home the Kasper gold.

Gladiator challenge

The final challenge of the day was the Gladiator Challenge, where a faction of skaters battled for supremacy of the ring while trying to stay on their boards. Round after round, they fought valiantly, with Alexis Lacroix, Sluggo, Dustin Henry and Lee Yankou being the finalists. Their final blitzkreig was fraught with peril, but Lee Yankou emerged victorious like a skateboard Spartacus.

The awards ceremony at the end saw Sluggo and Lee Yankou crowned as the MVPs, each taking home $250K. I thought for sure the advertised “$1,000,000 prize purse” was a troll, but nope, the math added up — the Dime Glory Challenge, a for-fun-only skateboarding shitshow, gave away a million Canadian dollars in prize money. Total madness. ■

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