Heelys shoes are a novel athletic shoe with a concealed wheel. They have been popular among youths since their introduction in 2000. This case study serves as a first look into the biomechanical implications of Heelys shoes on gait. Pressure readings of the forefoot, midfoot, and rearfoot during ambulation in regular athletic-shoe walking, Heelys without the wheel walking, Heelys with the wheel walking, and Heelys skating with the wheel were recorded on a single subject using the Pedar X System. A visual gait analysis was also performed on the subject. The resulting data show increased forefoot and rearfoot pressure while walking with the Heelys with the wheel. The visual gait analysis showed a diminished heel strike and a more rapid forefoot loading. These results demonstrate that Heelys do in fact affect the biomechanics of gait.