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Jeff Dechesare to Join Tim Pool’s The Boonies for Skate Night Contest, Winner Takes Home $3K

Good luck Jeff Dechesare!
ShreddER August 20, 2025
Jeff Dechesare on The Boonies Skate Night Contest
Credit: Jeff Dechesare; The Boonies; Tim Pool

Professional skateboarder Jeff Dechesare is set to compete in Tim Pool’s Skateboard company.

As we previously reported, The Boonies’ Skate Night contest will make the winner take home $3,000.

People in the skate community have been talking a lot about it, especially the core dudes who feel like Dechesare’s stepping a bit outside the usual scene by linking up with Pool’s The Boonies Skateboards brand.

Dechesare didn’t shy away from the chatter. He explained that the opportunity is mostly about the financial side.

"Yeah, I know you guys are bummed to see me in this, but the money is too good," he said. "They’re giving me $1,000 just to show up and $3,000 to win one game of skate. Plane and hotel are covered too. I might be losing a little pride here, but your boy is low on cash right now, haha."

Not everyone was quick to judge. One skater from the scene offered support, saying, "Don’t worry about these people. They don’t know what it’s like to put your whole life into skating. You gotta take the opportunities you can and keep rolling. The scene is at a low point anyway. At least you’re not going to extreme lengths like some others."

Jeff made it clear that his involvement is strictly for the contest and nothing more. "I’m literally just going there to play this game of skate," he said. "I’m not joining The Boonies or anything like that. Like someone else said, I’m just going in to get the bag and that’s it."

The Skate Night contest has everyone hyped, and while some purists might shake their heads, Dechesare is focused on the challenge and the prize money.

It shows that even contest pro skaters like Dechesare have to think about the paycheck sometimes, not just the love of skating.

The Boonies Posted:

"Saturday! August 30th! Boonies HQ presents SKATE NIGHT 1 - @shaunhover VS @jeffdechesare - Winner takes home 3k. Streamed LIVE on Rumble & YouTube. Starting at 5pm EST, with 2 undercard games prior the main event."

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A post shared by The Boonies HQ (@boonieshq)

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Previous Anti-Woke Skateboarding Team The Boonies to Host Skate Night on August 30, Winner Takes Home $3K
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