We study the evolution of shear bands in granular media subjected to very large deformations using the orthogonal cutting geometry. We perform our cutting experiments on Cauvery Delta sand with d50 of 0.45mm. We also capture images of the cutting process which allows us to perform a PIV analysis to determine the deformation in material around the cutting tool. In our experiments we observe that the dynamic angle of repose of the pile that forms in-front of the tool as cutting progresses, approaches the critical state friction angle of the material. We observe a flow bifurcation around the tool as the material begins to slip along planes which are oriented at an angle of π/4 – θ/2, θ being the dynamic angle of repose, to the cutting direction. This leads to formation of shear bands/velocity jumps which contain around 14 particles. A measurement of dilation angle within the shear bands indicate that material is in a critical state of deformation.