The failure and instability process of surrounding rock in deep engineering is accompanied by energy accumulation and dissipation and results in damage and failure, which play an important role in the inoculation and occurrence of rockbursts. The bursting liability, energy transformation, and total damage evolution during the coal failure process were investigated using uniaxial compression tests. A damage evolution model and constitutive relation were developed in which the initial damage is considered, and the primary fissures of the specimens were also observed from their computed tomography images. Sieve analysis was used to determine the size distribution of the fragments, a crushing energy formula model was developed that is associated with the fractal dimension, which corrects the energy dissipation of coal in the total process of deformation and failure. The relationships among the crushing, surplus energy density, and fractal dimension of coal with different bursting liabilities were explored in detail.