User blog comment:EmpyreanSmoke/Supernatural Q&A/@comment-26943316-20151026085023/@comment-24834479-20151026235912

1. He sold his soul and got dragged to Hell by a hellhound.

2. Billie meant and that Death thought it was funny how the winchesters were being brought back over and over, but now that he is gone, the natural order will continue with them as well.

3. In a lot of cases.

4. Tune in this Wednesday ;)