<p>Deep drawing of metallic materials presents several limitations, including stamped depth, wrinkle occurrence, total deformation after sheet fracture and the production of solids with uneven wall thickness. Regarding these variables, this work focuses on studying and correlating the mechanical and structural behavior of AISI 441 after a deep drawing operation for two initial conditions of this material. Mechanical characterization was performed on samples taken from the stamped cups’ base and walls using a novel shearing technique. The results are related to the respective texture characteristics of AISI 441. The structural analysis was conducted using transmission electron microscopy and electron backscatter diffraction methods. The findings concerning the shearing test validated the influence of the initial condition and the corresponding dislocation arrangement on the mechanical behavior of stamped AISI 441 steel, revealing hardening in the cup walls and softening at the base. Furthermore, the influence of the strain path on softening was observed in rolled samples compared to as-received ones taken from the cup walls. Notably, the rolled condition showed a shift in grain misorientation and an increase in the γ-fiber texture of the AISI 441 steel.</p>