An article of footwear with a shock absorbing heel system is disclosed. The heel system includes a lower heel plate, a set of support members, and an upper heel plate. Also, the heel system includes a heel cover configured to hide the upper heel plate from view. The lower heel plate is associated with a cantilever portion that supports the upper heel plate laterally. As force is applied to the heel system, the support members may compress slightly and the cantilever portion may lower, absorbing energy and or shocks applied by the ground.