Your trailer brakes are not braking as much as they should. When properly set, the brakes will hold the trailer to the rear of the hitch, thus not allowing the pin to move in the hitch. All hitches have play in them, if allowed to move very much or often, it will damage the pin and the hitch.
2021 Ram Limited, 3500, Crew Cab, 1075FTPD of Torque!, Max Tow, Long bed, 4 x 4, Dually,
2006 40' Landmark Mt. Rushmore