RE: How does this happen? (pic)
It appears that your cases have a 'military' style crimp on the primer pocket. I don't believe it is part of the primer. If that is the case (no pun intended), you may want to buy yourself a primer pocket swager (RCBS) to remove the crimp and allow you to seat new primers. I purchased 1000 Federal (FC) .223 once fired cases on Ebay and had to swage every one prior to repriming.
If you use too much pressure trying to seat the primers, you could damage them particulary the anvil and have misfires.