The evolution of the corticospinal tract (CST) is closely linked to the development of skilled voluntary movements in mammals. The main evolutionary divergence concerns the position of the CST within the spinal cord white matter and its postsynaptic targets in the grey matter. Here, we examine the developmental steps contributing to the CST projection pattern from an evolutionary point of view. Recent studies have highlighted the molecular mechanisms involved in these processes and how they relate to the acquisition of skilled movements. Comparison of the evolution of the CST in different species offers a new perspective on manual dexterity. In particular, it adds a new level of complexity to the classic view linking the evolution of the CST and the sequential improvement of skilled hand movements from rodents to primates.