I’ve got $5 (CAD) on it: betting on the future of skateboarding in 2026
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The problem with sports has been fixed. For far too long, there were too few ways for us, the viewers, to get involved with what was happening on the pitch, field, rink, court, course, ring, whatever. Sure, we could watch these sports on a screen or in person, grow attached to the athletes as we admire their routinely gobsmacking physical feats, and develop a bond with a team through shared experience and tradition that over time becomes a burning, passionate fandom, providing a whole separate community of real human people that you can immediately relate to and connect with, but how're you gonna make any money off of that shit?
We all know that's what we need to really feel something — stakes. Personal, financial. The legalization and proliferation of sports betting have transformed the world in just a few short years by enabling us to up the ante on everything. DraftKings, FanDuel, sketchy offshore crypto casinos like Stake — these online sportsbooks are available day or night; simply pull out your phone and wager on almost any game or event. If you really want to feel an emotional attachment to your favourite athletes, drop this month's rent on a parlay that hinges on their performance. You may wind up loving them even more or sending them death threats in their DMs, something players in all major sports leagues report being on the receiving end of, as hordes of broke, desperate, disaffected gamblers waste what little wages they have on an obscure over-under.
That might seem concerning, but at the end of the day, this is all about making a little (or a lot of) cash off of a thing you already enjoy; what's the harm in that? Well, besides the countless lives destroyed by it, the sharp increase in high-profile athlete-related betting scandals, and a growing number of people who believe the integrity of the games they love is being compromised by a parasitic industry that has nearly subsumed them. Speaking of subsuming, last year, FanDuel acquired 16 struggling sports networks and rebranded them the FanDuel Sports Network. Last week, news broke that the FSN "might be done." That's called betting on yourself.
Now, gambling, the silver bullet for a hum-drum sports fandom existence, has come for our everyday lives thanks to "prediction markets" like Kalshi and Polymarket, where the goal is, as Kalshi CEO Tarek Mansour put it at a conference in October, “to financialize everything and create a tradable asset out of any difference in opinion.” Awesome.
With these platforms, you can already bet on politics, war, and more, like who is going to win Thrasher Magazine's coveted Skater of the Year award.
That's healthy. No need to worry about the risks inherent in being able to place bets on the real-time happenings of our modern world, because, if you think about it, the real and present danger is in you not betting. The threat is that you're missing out on a payday.
Especially since you can now bet on skateboarding. From Stake becoming Street League Skateboarding's presenting sponsor and offering live odds during broadcasts to the forthcoming Professional Skateboarding League, X Games League, and Skate Board Association, all promising fans the ability to bet big on competitive skateboarding action. Because, well, how else are you gonna make any money off of that shit?
That brings us here, to "I've got $5 (CAD) on it," Simple Magic’s 5th annual year-end sports and culture gambling column, where you’ll find the world's most trusted skateboarding-related futures predictions and betting odds.
I'll put my airtight oddsmaking to the test by placing (an imaginary) $5 (CAD) on fifteen predictions to see how they fare once the year is up. Below, you’ll find the results from 2025, followed by my 2026 projections, whose accuracy is sure to border on clairvoyance come December.
Betting on the future of skateboarding in 2025: RESULTS
(+135) DVS Shoes' directionless revamp releases a promo video, which is surprisingly decent. The company goes dormant once more before the year is up.
RESULT: Bust. DVS did not release a promo and has not gone dormant, but they also haven't done much of anything beyond serving as an auxiliary social media account for The Berrics.
PAYOUT: $0 (CAD)
(+100) Zombie Lakai reveals its new team on January 31, and at least one rider affected by recent Etnies and Emerica layoffs is on board.
RESULT: Cashed. Sort of. Chris Joslin was let go by Etnies at the beginning of the year and joined the team at Lakai later in 2025, eventually winning Thrasher's Skater of the Year; he just wasn't announced on January 31. I'm still taking this one, though.
PAYOUT: $10 (CAD)
(-300) In a bleak twist, Cariuma carries more industry credibility than DVS and Lakai by year's end.
RESULT: Bust. Despite the odds, this was always a long shot, but given how both DVS and Lakai have been run, taking a flier wasn't the worst call. If it weren't for Joslin, I would've won big. I swear.
PAYOUT: $0 (CAD)
(+300) A new product gimmick is introduced to the skateboarding world, and, for a brief, confusing moment, everyone is stoked.
RESULT: Cashed. 2025 saw the announcement of three separate skateboarding "leagues." From Mike Mo's PSL, the X Games League, and the increasingly confounding Skate Board Association.
Cole Nowicki
These leagues represent a new product gimmick, but is everyone stoked? It might be difficult to tell when organizations like the SBA remove any mildly critical comments from their Instagram posts, or if they block you like they did me, for, I assume, my previous reporting on them. But when you see interactions like this, where SBA co-founder Sheldon Lewis, who handles the SBA's social media, appears to be talking to himself in the comment section of an SBA Instagram post, you can feel the authentic stoke through the screen.
PAYOUT: $20 (CAD)
(+200) A skateboarder breaks new ground by being the first to receive a signature-model shoelace.
RESULT: Bust, but only because of industry cowardice! Someone give someone a PRO 'LACE! (A reader noted after publishing last year that Micky Papa once had a signature shoelace belt with Lacorda Threads, but this bet is based on a signature shoelace specifically for shoes.)
PAYOUT: $0 (CAD)
(-100) Jared Kushner is embroiled in a scandal after a story breaks that reveals another disturbing slate of investors in his already vast private equity firm. Harmony Korine's project EDGLRD, a rumoured Kushner beneficiary, is accused of accepting blood money.
RESULT: Cashed? It was already reported that Kushner is essentially playing dress-up with billions worth of Saudi Arabia's money, and now Qatar and Abu Dhabi's, and is primarily using his connections to the Trump administration to curry favour and promise regulatory expedience, like in deals to purchase Electronic Arts and a hostile takeover bid of Warner Bros. Discovery (before his firm, Affinity Partners, pulled out of the latter deal).
So, if the stink coming off of Kushner somehow wasn't already apparent, a recent failed Affinity project to build a Trump International Hotel in Serbia led to several local politicians being charged with corruption. The firm is also the largest shareholder in an Israeli financial company that "holds shares in businesses accused by the United Nations of operating in illegal settlements in the occupied Palestinian territories," per Business and Human Rights Centre.
In 2025, EDGLRD's already weak public standing in the skateboarding space took a nosedive, prompting marquee riders like Mike Arnold and Vincent Touzery to quit the team. Those departures and reputational decline can be chalked up to a whole host of other issues, most relevant being the company's paralyzingly bad debut full-length, Point Cloud, but the rumoured Kushner connection (which remains just a rumour, only Korine and Kushner's friendship has been reported on) probably doesn't help. I'm taking it.
PAYOUT: $10 (CAD)
(+350) EDGLRD releases an app that filters skate clips to make it look like the skateboarder is a demon with a skin condition and bad posture. The app is later revealed to be a Trojan horse for Israeli spyware.
RESULT: Bust. However, EDGLRD did release this keyboard, which feels equally pointless.
PAYOUT: $0 (CAD)
(-200) Cordano Russell does a fakie-frontside-180-frontside nosegrind down a handrail.
RESULT: Bust. I was confident I'd seen Russell land one somewhere this year, in the street or in Street League, but I couldn't find the video evidence. I went so far as to reach out to Tum Yeto auteur Don Luong to ask if he'd ever seen the Toy Machine PRO rideaway from such a maneuver. He was also pretty certain Russell had, and reached out to him directly to confirm. The Team Canada member shattered our shared reality: he had not. Damn.
However, if he does in the future, I think it's safe to consider Don and I as the inspiration.
PAYOUT: $0 (CAD)
(-120) Skateboarding's big trend for 2025: Christianity.
RESULT: Cashed. However, in retrospect, it's wrong to call it a trend. There has always been a significant undercurrent of Christianity in the professional skateboarding space, but most followers aren't overly vocal about it (with notable exceptions like Brian Sumner, Jamie Thomas, Lance Mountain, Lennie Kirk, and, as we saw recently, Steve Caballero). That's changed.
From the aforementioned Cordano Russell charmingly requesting that the holy spirit activate before attempting tricks, Kyle Walker finding and proclaiming his faith, Felipe Gustavo and Vincent Milou apparently employing the services of a "chaplain," to Mikey Taylor running his financial influencer shtick through a dubious Christian lens, the believers are out and loud.
PAYOUT: $11 (CAD)
(+250) A non-American wins Thrasher Magazine's Skater of the Year award.
RESULT: Bust. TJ Rogers... the underdog... he was so close... I almost had this one... victory... so sweet... so far.
PAYOUT: $0 (CAD)
(-100) Primitive Skateboards gives Andrew Huberman a guest pro model.
RESULT: Bust. Which, in its own way, is a win.
PAYOUT: $0 (CAD)
(-150) Real Skateboards turns Momiji Nishiya PRO AF.
RESULT: Bust. Nishiya had a standout section in Real's Oval (and somehow didn't make the SOTY longlist) and could very well have gone PRO AF, but Real is being patient, much to my chagrin, and just officially announced her addition to the team in late December.
PAYOUT: $0 (CAD)
(+400) The Nine Club runs out of relevant or interesting skateboarders to interview, so they invite me to be on as a guest.
RESULT: Bust. As was expected, there are still more relevant and interesting skateboarders out there, and there likely always will be.
PAYOUT: $0 (CAD)
(-500) New skateboarding media ventures flourish.
RESULT: Cashed. Skate Bylines, Dolores, Bubble, Skatefolio, The Den, Downward Skateboard Magazine — while not all of them are new-new, they've all been hitting their stride as of late, adding a fresh depth to a once fallow media landscape.
PAYOUT: $6 (CAD)
(-1500) You continue to love and be loved.
RESULT: Cashed. Easy.
PAYOUT: $5.33 (CAD)
PREDICTIONS RECORD FOR 2025:
Cashed: 6/15
EARNINGS: $62.33
TOTAL WINNINGS: -$12.67
2025 RESULTS: I started with a hypothetical $75 (CAD) and ended the year in the red with a hypothetical $62.33 (CAD). That may seem like a loss, but you never lose when you bet on yourself. Unless you're betting real money, then it's gone.
Betting on the future of skateboarding in 2026: PREDICTIONS
(-100) Out of the PSL, SBA, and XGL, only one league remains operational by the end of 2026.
(+250) The Skate Board Association fails to host a single event in 2026.
(-150) Ginwoo Onodera lands a bigspin-kickflip-frontside-bluntside-bigspin-kickflip.
(+175) Arisa Trew lands a 1080.
(+200) At the end of 2026, Chloe Covell sits at the top of the World Skateboarding Rankings for "Female Street."
(-100) At the end of 2026, Ginwoo Onodera sits at the top of the World Skateboarding Rankings for "Male Street."
(+250) Sven Kilchenmann has himself the Comeback of the Year.
(+175) Two or more new skateboarding shoe companies launch.
(+100) In an official statement, Independent Trucks announces that they've brought back their iron cross logo and decry censorship. Tim Pool claims the move as a victory against the woke mind virus.
(+100) Independent Trucks once again moves away from the iron cross logo after facing backlash from critics and praise from white nationalists.
(-300) Generative AI slop usage in the skateboarding space spikes, prompting widespread disgust, before it mercifully falls out of fashion.
(-350) Social media continues to tear at the fabric of society, providing more opportunities for beloved professional skateboarders to reveal themselves to be complete dipshits.
(-200) 2026 sees even more in-person events, including demo and video-premiere tours, signings, open skate jams, and more.
(+175) Dashawn Jordan inks a vodka sponsorship to go along with his Minute Maid sponsorship and drops a new track called "Screwdriver" to celebrate
(-2000) You continue to love and be loved.
A Simple Magic 2025 wrap-up
As I like to do around this time, I want to extend a big Thank You to everyone who reads and subscribes to this newsletter. Especially those Custodians and Champions of Simple Magic who made the questionable but admirable decision to give me their monies.
It was a good year for Simple Magic. Subscriber count grew at a slow but steady clip, with 241 new sign-ups. Across 62 total posts, the newsletter's average open rate was 60%, which is solid. The post with the most web traffic was, by far, this one, likely due to people doing some googling after this Whitney Cummings post. According to Ghost's new internal analytics, which went live in July, the site has readers in at least 47 countries. Shout out to the 'sletter heads in China who apparently accounted for 16% of all Simple Magic's web traffic.
Beyond boring numbers, we did some cool new stuff, like teaming up with Farran Golding at Skate Bylines on an experimental video project, collaborating with Dirt on a series of essays and a scent, making some hats for the 'sletter sickos out there, and I had the opportunity to be a guest speaker and talk about this project and others in Keith Plocek's "Storytelling for Action Sports" class at the University of Southern California.
I'm also quite proud and excited about all of the contributors who wrote for Simple Magic in 2025. I was fortunate to publish 15 pieces — standalone and in the Friday Post — by a lot of my favourite people. What a blessing.
Alright, that's about enough of this. Thank you again. Here's to another year of more, different, and (hopefully) good.
Something to consider:
Good thing:
Scott Saul
Another good thing:
Jaime Owens
A good 2025 sports moments thing:
Defector Staff
A good thing about a bad thing:
Spencer Ackerman
Good Ryan:
A good piece on Exposure:
A good pod round-up:
Posted by
Templeton
New home for New "Rules":
Farran Golding
A brickbank thing: A year of hanging out with my friends on our lunch breaks.
Until next week… new year, new you. Or old you, that one is great, too.
Laser Quit Smoking Massage
NEWEST PRESS
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My new collection of essays is available now. I think you might like it. The Edmonton Journal thinks it's a "local book set to make a mark in 2024." The CBC called it "quirky yet insightful." lol.
Book cover by Hiller Goodspeed.
Right, Down + Circle
ECW PRESS
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I wrote a book about the history and cultural impact of Tony Hawk’s Pro Skater that you can find at your local bookshop or order online now. I think you might like this one, too.
Here’s what Michael Christie, Giller Prize-nominated author of the novels Greenwood and If I Fall, If I Die, had to say about the thing.
“With incisive and heartfelt writing, Cole Nowicki unlocks the source code of the massively influential cultural phenomenon that is Tony Hawk’s Pro Skater, and finds wonderful Easter-eggs of meaning within. Even non-skaters will be wowed by this examination of youth, community, risk, and authenticity and gain a new appreciation of skateboarding’s massive influence upon our larger culture. This is my new favorite book about skateboarding, which isn’t really about skateboarding — it’s about everything.”
Photo via The Palomino.
