Wolcott - who prefers to go by "Red" - is one of the very best transition and bowl skaters in the country in his age group.
It's a skill-set he's earned. Ask him how much he's on his board each week and he'll tell you "an uncountable amount of hours."
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His mother Cheryl homeschools Red to allow greater flexibility for travel to competitions and events. She's a necessary partner in his passion. "I get to sit at the hot skate park every day of the week for hours on end. I meet a lot of nice people. We really enjoy the culture," she said.
It's no secret where Red gets his nickname, but he says his hair serves a purpose far more important than fashion.
"My hair is my power. If you cut my hair, I'm not the same person."
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Still a week from his 11th birthday, Wolcott hopes to become a pro skater one day. He's tried other sports, but the skate life is the life for him.
"In my eyes, skateboarding isn't a hobby or sport to me, it's a lifestyle."