Tim O'Connor

Not only is the pop on this kickflip unbelievable, the fact that he did it while wearing Air Force Ones(impossible to skate in, for me at least) makes it that much more special. I don't think that Tim O'Connor gets nearly enough credit for his progressive ledge game over the years, and I feel that along with a couple of other dudes he really sparked the awkward 180 or shove-it out of a grind in the middle of a ledge thing, although he makes it look about as far from awkward as you can get. Which was even more impressive considering he did it when everybody else seemed to be stuck flipping into crooked grinds or slithering across orange plastic barriers with jump ramp assistance.
(Anyone else remember that old Firm commercial from 411 where Ray Barbee laced a f/s nosegrind revert in the middle of a ledge? That's the kind of shit I'm referring to.)
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