Abstract: A flagpole assembly includes a hollow pole and a winch at the base of the pole. A halyard is connected to the winch, extends through the hollow pole and out an exit opening at its tip. The inner edge of the flag is removably mounted to fixed positions along an elongate flag trolley to keep the inner flag edge extended. The flag trolley includes an elongate U-shaped channel to which two pulleys are mounted. The halyard passes from the exit opening, around one pulley, between the legs of the channel and around the other pulley. The outer end of the halyard is fastened to a shock absorbing anchor mounted along the hollow pole. Winding and unwinding the halyard onto and from the winch causes the flag to raise and lower as the length of the halyard between the exit opening and the anchor increases and decreases. The weight of the flag trolley, with or without the flag, is sufficient to pull the halyard from the pole when the winch is unwinding the halyard.