The crew was in the process of pulling the transformer from the pole using a steel Wilson gin. All of the work was being done by a journeyman climber on the pole. The crew had covered the 12kV primary above while making the lift when the winch line became very taut. The operator reported 1000 lbs. of pressure on the capstan pressure gauge. After several attempts to work the transformer from the pole the transformer came loose and was ejected from the pole an estimated 18”. The transformer remained attached to the fiber sling and winch line but the violent action shook the pole top and primary. The rubber cover prevented the equipment from coming in contact with the primary. The crew found that the transformer hanger had been flattened out preventing it from easily being lifted from the pole.