A skateboard truck assembly with an integrated combination of a system of gears that resemble planetary gears that allow both wheels and a caster to remain on the ground while the skateboard is traveling in a lengthwise manner. At the same time, when the rider leans to one side or the other of the skateboard, the gear assembly causes the “downhill” wheel to rise in the air and the caster to be displaced such that the skateboarder can laterally “slide” or “drift” the skateboard as though it was a snowboard. Because the downhill wheel is raised well above the ground, there is less of a tendency for the downhill wheel to catch on any street irregularities or rocks and stop sliding at inopportune times.