Skate legend Jason Jesse has always been one of skateboarding’s most outspoken figures, and he recently proved again that he isn’t afraid to share what’s really on his mind.
The 55-year-old took to Instagram to post a simple but strong message that had a lot of skaters shocked.
In a photo with a caption, he wrote: “Cautionary example. Never sign skateboard contracts.”
It didn’t stop there as he followed it up with another post saying: “Thank you for giving me the opportunity to say no thank you.”
This feels like a classic Jason Jesse.
He’s never been the type to just go along quietly with the way things are done in the industry.
He’s pointing out something that many skaters, especially younger ones, might not think about when sponsors and companies come calling.
Contracts in skateboarding can look like a dream on the surface.
A company offers free stuff, money, or a bigger spotlight. But Jesse’s words suggest that once you put your name on paper, it might not always play out the way you hoped.
It could mean giving up control over your own image, your freedom to ride for who you want, or even the way you express yourself on and off the board.
Jesse’s advice isn’t about telling skaters to turn their backs on opportunities.
It feels more like he’s asking people to think twice before signing something they don’t fully understand. He’s using his own experience as a warning, putting the choice back into the hands of the skaters themselves.
The skateboarding world has always been about independence and self-expression, and Jesse’s comments line up with that history.
It’s not about corporate deals or fine print, it’s about the skateboarding itself and the community built around it.
So when Jesse says, “Never sign skateboard contracts,” it’s not just like a whatever kind of BS. It’s the freedom to skate how you want and live on your own terms might be worth more than anything written on paper.