The wheel brake system safety is a complex problem which refers to its technical state, operating environment, human factors, etc., in aircraft landing taxiing process. Usually, professors consider system safety with traditional probability techniques based on the linear chain of events. However, it could not comprehensively analyze system safety problems, especially in operating environment, interaction of subsystems, and human factors. Thus, we consider system safety as a control problem based on the system-theoretic accident model, the processes (STAMP) model and the system theoretic process analysis (STPA) technique to compensate the deficiency of traditional techniques. Meanwhile, system safety simulation is considered as system control simulation, and Monte Carlo methods are used which consider the range of uncertain parameters and operation deviation to quantitatively study system safety influence factors in control simulation. Firstly, we construct the STAMP model and STPA feedback control loop of the wheel brake system based on the system functional requirement. Then four unsafe control actions are identified, and causes of them are analyzed. Finally, we construct the Monte Carlo simulation model to analyze different scenarios under disturbance. The results provide a basis for choosing corresponding process model variables in constructing the context table and show that appropriate brake strategies could prevent hazards in aircraft landing taxiing.