Monodisperse packings of dry, air-fluidized granular media typically exist between volume fractions from $\Phi$= 0.585 to 0.64. We demonstrate that the dynamics of granular drag are sensitive to volume fraction $\Phi$ and their exists a transition in the drag force and material deformation from smooth to oscillatory at a critical volume fraction $\Phi_{c}=0.605$. By dragging a submerged steel plate (3.81 cm width, 6.98 cm depth) through $300 \mu m$ glass beads prepared at volume fractions between 0.585 to 0.635 we find that below $\Phi_{c}$ the media deformation is smooth and non-localized while above $\Phi_{c}$ media fails along distinct shear bands. At high $\Phi$ the generation of these shear bands is periodic resulting in the generation of ripples on the surface.