post a photo of the foot of your mast, and the tabernacle... its possible the holes are in the wrong position and its bending when raising and lowering..
when the mast is in the working position, the mast should bear on the tabernacle and NOT the pin, and the pin should be not be tight, but only snug so it holds the foot of the mast into position. if the pin is tight, its puts unnecessary stress on the tabernacle.
when raising and lowering, you should always keep the pin loose so it does not bind.
if your rigging is out of proper adjustment, but snug, it should not have any affect on the pin, but if the pin hole in the mast and the hole in tabernacle does not align properly, it can bend the pin when the rigging gets loaded.... a couple pics could help us identify your problem