Detection and severity assessment of subdural hematoma is a major step in the evaluation of traumatic brain injuries. This is a retrospective study of 110 computed tomography (CT) scans from patients admitted to the Michigan Medicine Neurological Intensive Care Unit or Emergency Department. A machine learning pipeline was developed to segment and assess the severity of subdural hematoma. First, the probability of each point belonging to the hematoma region was determined using a combination of hand-crafted and deep features. This probability provided the initial state of the segmentation. Next, a 3D post-processing model was applied to evolve the initial state and delineate the hematoma. The recall, precision, and Dice similarity coefficient of the proposed segmentation method were 78.61%, 76.12%, and 75.35%, respectively, for the entire population. The Dice similarity coefficient was 79.97% for clinically significant hematomas, which compared favorably to an inter-rater Dice similarity coefficient. In volume-based severity analysis, the proposed model yielded an F1, recall, and specificity of 98.22%, 98.81%, and 92.31%, respectively, in detecting moderate and severe subdural hematomas based on hematoma volume. These results show that the combination of classical image processing and deep learning can outperform deep learning only methods to achieve greater average performance and robustness. Such a system can aid critical care physicians in reducing time to intervention and thereby improve long-term patient outcomes.