It looks like he's surfing or water skiing or skitching down Gasoline Alley...all of which are against IMS policy.
The Urban Dictionary defines skitching as follows:
|The act of being pulled by a mechanized conveyance(car, truck, tractor, etc) while operating a non-mechanized conveyance (skateboard, skates, bicycle, handcart, etc). Extremely dangerous but a lot of fun, as you get going wicked fast.|
Yes. Jay Howard is the Hot Rod Stewart of shiny and fast Indy racing!