DERG
It's a bit clearer to me. You state that "Oil was getting in, and hot air." Are you saying this opening is part of a closed system? I repeat my question that the end of this pipe appears to be half of a line coupling, and losing the integrity of the line as the coupling failed may have caused the oil to drown the bearing case? Why is a counter bore necessary at all if this is a terminus to a (unpressurized, and un-checked 'feed')?
bear