Due to the large inertia and strong impact accompanying the free-falling hook process of crawler cranes, it is difficult to meet the demand for flexible and smooth braking control under different weight load conditions. Therefore, this paper takes the free-fall hook system as the research object and combines system operation characteristics and control theory to carry out research on flexible braking control of the free-fall hook system. Firstly, a joint simulation platform of MATLAB (version 2018b) and AMESim (version 2019.1) software is built to theoretically analyze the key components of the free-fall hook system (proportional pressure-reducing valve, winch reducer, and wet clutch). Secondly, a mathematical model of the braking process is established, and the pressure control demand is clarified to analyze the reasons for the existence of dead zones and hysteresis loops in the system. Meanwhile, it is found that the dead zones and hysteresis loops existing in the pressure output of the pressure-reducing valve are the main factors of flexibility with load braking. Then, in this paper, a closed-loop control strategy is formulated based on the automatic adaptation of the braking gear in combination with the fuzzy PID pressure. Finally, the effectiveness of the control strategy proposed in this paper is verified with simulation and experimental testing using the pressure hysteresis loop of the free-fall hook process and the load-braking acceleration as the judging criteria. The results show that the system pressure hysteresis loop is reduced by 50%–60% and the maximum braking acceleration is reduced by 24%–30% under the conditions of 6.44 tonnes and 10.44 tonnes, which improves the accuracy of pressure control and achieves flexible and smooth braking with loads for different tonnages of free-fall hooks.