in basketball, when a player crosses his defender over so viciously that the defender loses his balance and appears to be a novice roller/ice skatertrying to regain his balance.
This is Westcountry slang dating back to before the First World War. Skates are very slippery fish and the name was applied to people who had slippery natures in that they were untrustworthy, would try to avoid giving information or were just not very likeable. The use of the name expanded to include people who were wheeler dealers or people who do a lot of ducking and diving but no actual work. The name is disparaging but at the same time may hold just a hint of reluctant admiration. It is, however, a warning as a skate has no conscience and is totally unscrupulous and untrustworthy. The term is believed to have been used extensively by the British armed forces and was used to describe someone who was a slippery customer, fishy and who avoided their share of the work.
The good ol' plank o' wood. A skateboard is NOT a toy; it's a part of your fucking life, bro. Cruise to school, bomb hills, haul ass, eat shit, and learn a thing or two from and on your board. A skateboard has always been there. Get on and forget all the bullshit; enjoy the ride. You CANNOT use a skateboard as a fashion sense; if you do, you're a shithead. Thrash everything in sight and ride until you die.
Fuck doing homework. I have my skateboard.
Fuck doing drugs. I have my skateboard.
Stereo types aside, it's just a thing that some people like doing. Frowned upon by cops, business owners, and midle aged rich stuck up Bitchy women. You get kicked out of anywhere you can think off by just skating flatground.
HEY! THERES NO SKATEBOARDING HERE. YOUR DAMAGING THAT LEDGE!!!