'69 Bcuda 340 loses cam plug in rear of engine

The ring came off the flywheel on this 340/AT show quality car that is babied and never pushed. He replaced it and then it started leaking oil badly from the back of the engine- thought the rear main just decided to fail, but that DIDNT fix it either. This time a close inspection revealed that the broken flywheel ring had somehow knocked that cam plug out and chipped the block. Its fixed now, has anyone ever seen this issue on other Mopars?
Any pics? Was it a dished plug?