I’ve got $5 (CAD) on it: betting on the future of skateboarding in 2023

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I’ve got $5 (CAD) on it: betting on the future of skateboarding in 2023
Now, you might be asking yourself, where is the regular Friday “Simply Ranked” post? What is this? More End of Year content? Jesus Christ. Well, the answer to that is a firm, unapologetic yes. This is more EOY content. Why? Because I’m lazy. Also, last year at this time, I had a segment in the usual Friday post called “I’ve got 5 CAD on it: betting on the future of skateboarding in 2022,” where I predicted a variety of things that might happen in the world of skateboarding at large and provided betting odds on how likely it was that those predictions would come to pass. So I thought it might be fun to expand on that by following up on last year’s results, see how I would’ve fared if I treated this like some half-baked sports betting column and put a $5 (CAD) bet on each prediction, and then make a series of new predictions for what’ll go down in skateboarding in 2023. Sound okay? Cool.

Betting on the future of skateboarding in 2022: RESULTS

Admittedly, last year, I didn’t put a lot of foresight into how I might continue this gimmick into 2023, so I made several predictions that are tricky to gauge the success or failure of. But, as the author of this newsletter, it is my duty to serve as its ultimate arbiter of truth and fairness, so I’ll do my best to only claim a “W” if it is deserved.

Full disclosure: I don’t understand how sports betting works. That said, after being forced to listen to the unceasing Draft Kings ad reads that have spread across every sports broadcast and podcast these last few years like a contagious flesh-eating fungus, I should be able to at least make it sound like I do. So, on that note, let’s get into it. Here are the eleven predictions I made for 2022, how my hypothetical $5 (CAD) bets for each went, and what state my hypothetical $55 (CAD) bankroll was left in by the end.

(-200) The agents of popular professional skateboarders attempt to gain favourable coverage of their clients from Gifted Hater.

BUST: Didn’t come to pass, at least publicly. Who knows how many DMs GH received from the Stoked Management group.


(-150) Board brands realize they can have more than one woman on their teams at a time.

WASH: Some teams have! But most haven’t. Let’s call this one a wash.


(-100) Brandon Turner one-ups himself to land the biggest switch hardflip of all time.

BUST: In the wake of Turner’s astounding comeback year and Wallenburg switch hardflip in 2020, I found myself enraptured by his return, assuming it would continue at the same clip as previously. That wasn’t to be—at least in 2022.


(-150) The Berrics and all of its IP are bought by the subscription-based diet app Noom.

BUST: This was always a longshot, but considering how The Berrics appears to have survived by essentially becoming a Cariuma-branded media arm this past year, with most of their original content plastered with the shoe company’s logo or serving as explicit Cariuma promotion, it’s not like this one was totally out of the realm of possibility.


Tony Hawk Ruby Finger Flip from the Tony Hawk Last Trick NFT Collection.

(-250) Thrasher enters the NFT space, selling classic non-fungible covers.

BUST: The Bible stayed out of the non-fungible fray, but everyone from Tony Hawk to Mike Mo and Supra Footwear’s corpse, unfortunately, have not.


(+150) Mob Grip releases a full-length video, and it’s actually really good. Seriously.

BUST: Another reason to skate Jessup.


(-200) Rayssa Leal wins every Street League event she enters.

CASHED: Leal swept the SLS season, winning herself a grip of trophies, cash, acclaim, and me this bet.

PAYOUT: +$7.50 (CAD)

(-500) Your favourite AM turns PRO, and as you scroll through the celebratory Instagram posts that follow, you feel a sense of relief and satisfaction, as if all is finally right in the world.

CASHED: You let those waves of emotion pass through you multiple times this year. From Hugo Boserup, Nicole Hause, and Spencer Semien to Chandler Burton, a serious amount of “PRO AFs” were howled into the sky in 2022.


SIDE NOTE: None of my prop bet suggestions hit, but this doesn’t impact the final result because these were merely suggestions, okay?

Who’s turning PRO?

(-300) Shintaro Hongo
(-150) Rowan Davis
(+100) Nelly Morville
(+150) Shay Sandiford

(-200) The Lurpiv trucks case finds a second life as a weed container, outlives the use of Lurpiv trucks by years, decades.


PAYOUT: +$7.50 (CAD)

(-500) You finally learn that trick you’ve been trying forever.

CASHED: Damn, you’ve got it on lock now, eh. Stoked for you!


(-1000) You find love or continue to love and be loved.


PAYOUT: +$5.50 (CAD)

PREDICTIONS RECORD FOR 2022:  5/10 (one prediction was a wash, that hypothetical $5 [CAD] stays with me 😈)
PAYOUT TOTAL FOR 2022: Started with a hypothetical $55 (CAD) and ended the year with a hypothetical $37.5 (CAD). Damn.

Betting on the future of skateboarding in 2023: PREDICTIONS

From the dramatic to the mundane, I feel these 15 predictions and their odds of happening in my bones. Call it clairvoyance, intuition, instinct, or a simple yet indescribable knowing. Whatever the word, next year at this time, I’ll be calling it “cha-ching” due to all of the hypothetical money I’ll be taking out of or putting into the proverbial cash register. Not exactly sure how that’s supposed to go.

(+500) Thrasher’s 2023 Skater of The Year doesn’t ride for Nike, Converse, Adidas, New Balance, or Vans.

(+400) Someone leaks George Powell’s secret recipe for Powell’s Dragon Formula wheels.

(-300) Nick Matthews finally and deservedly turns pro after inexplicably spending years in board sponsor purgatory.

(-100) Nike continues to show a decreased interest in its skate program, axes a large portion of their team.

(-250) Eric Koston gets on Cariuma

(+200) Cariuma goes under.

(+150) Thrasher invites more than one woman onto 2023’s “Am Scramble.”

(+300) Tony Hawk gets investigated by the FTC for his promotion of NFTs.

(-100) Chloe Covell beats Rayssa Leal in at least one Street League event.

(-250) Mikey Taylor gets into (another) motor vehicle accident while driving his Tesla on autopilot.

(-1000) Again, you find love or continue to love and be loved.

(-100) Gustavo Ribeiro does a 360 flip nosegrind nollie flip out on a handrail.

(+1000) Rob Dyrdek’s Ridiculousness gets cancelled after 28 seasons on MTV.

(+475) Someone buys a Skate Mental board.

(-1,500) You and your friends go out skating on a beautiful summer day. There’s a light breeze that takes the edge off the heat. Everyone gets their tricks. Someone eats shit, but in a funny way, and they’re okay. The whole crew laughs. Someone tosses you a beer. A butterfly lands on your board and you get it to climb onto your finger before it flies away. The sun starts to set and your sweat begins to dry. You look around at all of your friends, and a wild and involuntary grin starts peeling across your face. This, you think to yourself, is the shimmering potential you always knew life held.