The derailments of empty wagons of long freight trains frequently occurred around the world, which caused tremendous losses every year. Aiming at an actual derailment of empty wagons on straight line during dynamic braking, the field investigation was conducted to find the reasons of the accident. According to the investigation results, the large coupler yaw angle and coupler force, the special connection mode by drawbars, as well as the poor conditions of wheel treads and flanges were supposed to be responsible for the accident. The simulaiton model composed of 3 C80-type gondolas, and two RFC-type drawbars is established, the accuracy of which is validated by the field experimental test. When the wheel-rail friction coefficient is set to be 0.7 and the coupler forces are set to be 350 kN with a coupler yaw angle of 7 degrees, the simulation results are consistent with the field investigation results. Simulation results indicate that the coupler yaw angle, coupler force, and wheel-rail friction coefficient have significant influences on the derailment. The increasing coupler yaw angle and coupler force will increase the risk of derailment. For the wagon units adopting the drawbars, the riskiest wagon changes from the middle wagon to the front one as the lateral components of the coupler forces increase. A large wheel-rail friction coefficient can raise the risk of derailment. However, an overlarge friction coefficient will decrease the derailment risk. According to the field investigation and simulation results, the wheel-rail friction coefficients should be limited below 0.5 to ensure the running safety of empty wagons. Besides, the operations of the train should be optimized to avoid large coupler yaw angle and coupler force.