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i won a pair of skis by default in a girls slopestyle comp cuz no one else was in it. then i sold them on ebay for 500 bucks because they were gay. legit, eh?
came first place in some skatecompetition at a near by skatepark once, got myself hooked up with a whole package of skate gear. I feel like that was a pretty good win.
also once when I was like 7 I won a whole boxload of pogs.
last season i won the Undie 500 at Echo. first place was a bunch of fate clothes, six concert tickets, a SoBe snowboard, free subscriptions to freeskier and snowboarding magazine, a $50 debit card, and an mp3 player... i'm pretty sure thats it but i dont really remember