The traditional probabilistic-based lifetime evaluation methods for motorized spindles neglect the effects of load dynamic and structure difference. Hence, a dynamic-model-based lifetime estimation method combining these effects is proposed to improve the estimating results for motorized spindles, especially in the design stage. Considering the bearings lifetime has dramatically influenced the reliability of motorized spindles, this paper establishes a shaft-bearing-toolholder based on a dynamic model to estimate the bearing group lifetime. The proposed dynamic model is closer to the actual structure in spindles, indicating the stiffness of bearings and contact surface conditional on the inputting radial-and-axial forces is nonlinear. The stiffness model is verified by finite element analysis and experiment. The load applied to bearings is accurately calculated through the dynamic model. Then, the load is introduced to a well-known bearing lifetime model, thereby calculating the lifetime of each bearing and its group. The bearing lifetime results under different conditions of preload, clamping force, and cutting force are discussed.