Groundwater inrush hazard has always been a great threat to the construction of vertical shafts in coal mines. Generally, the failure of the water-resisting coal pillar under coupled stress-seepage conditions around the vertical shaft is the main reason for the generation of the water inrush channel. In order to understand the mechanical behaviors of the water-resisting coal pillar, the strength of typical coal affected by the size and water content was investigated, and the stress sensitivity of permeability was investigated by a stress-seepage coupling test. The stress field and deformation of the water-resisting coal pillar were investigated by numerical simulation, the stability of the water-resisting coal pillars with different widths was evaluated, and the reasonable width of the coal pillars under coupled stress-seepage condition was determined. Results show that the water content and coal pillar width have a great influence on the mechanical characteristics of coal samples. Under the conditions of lower water content and larger coal sample width, the coal sample presents higher strength, smaller axial deformation, smaller permeability and porosity, and weak sensitivity to stress. The simulation results show that the boundary of the main roadway at the end of the coal pillar is dominated by tensile stress, and fractures can significantly contribute to the destruction of coal pillars. With the increase in the width of the water-resisting coal pillar, the internal damage variable, maximum tensile stress, porosity, and average water flow velocity of the coal pillar decrease, which reduces the risk of water inrush and improves the safety of the water-resisting coal pillar. An evaluation model of the reasonable width of the water-resisting coal pillar under the stress-seepage coupling was proposed, and the model was verified by the shear slip law and experimental results. This study provides theoretical and experimental guidance for the risk management of groundwater inrush disaster during the construction of vertical shafts in coal mines.