Here at POETV we tend to get bogged down in fetishes, politics & oddities of all kinds. I've always thought we could use more pointless injuries in the mix from time to time, and this fills that gap nicely.
Clearly, he was going to grab the branch, swing around a few times to build momentum, then launch himself over the overpass, landing on the still-moving skateboard and continuing down the road. At the zenith of his trajectory, he will crack open a frosty Mountain Dew LiveWire (tm) and wink roguishly at the camera.
It went off without a hitch during the unfilmed practice run, I swear.