Traditional management of unstable fourth and fifth carpal–metacarpal (CMC) fracture–dislocations (fx–dislocs) of the hand includes closed reduction and percutaneous pinning (CRPP) versus open reduction internal fixation (ORIF). Traditional trajectory of pin placement is toward the base of the hook of the hamate. Our case series of CMC fx–dislocs treated with this trajectory led to the development of ulnar deep motor branch symptoms (sxs). We attempt to propose an alternative trajectory that could lower the chance of iatrogenic injury. Five fresh frozen cadaveric specimens underwent percutaneous pinning of the fifth CMC joint using fluoroscopic guidance. Each cadaver was dissected, and the proximity of the deep motor branch of the ulnar nerve was measured in relation to a pin that penetrated the volar cortex. Our results confirm the close proximity of the deep motor branch of the ulnar nerve to the volar cortex of the hamate and demonstrate the potential for iatrogenic injury during CRPP of the fifth CMC fx–dislocs, especially with penetration of the volar cortex. By demonstrating the close proximity of the deep motor branch to the volar cortex of the hamate in cadavers, we highlight the potential for iatrogenic injury with CRPP of CMC fx–dislocs as seen in our case series. We recommend a more midaxial starting point on the proximal metacarpal with a trajectory aimed at the midbody of the hamate to prevent penetration of the hamate volar cortex and limit the chances of iatrogenic injury.