Quote - Why someone would want to give away copies of software they paid good money for, has never been clear to me. The pirating has to start with a paying customer somewhere.

Not especially, there are a lot of people in the chain from final production CD to "going to silver" for distribution.

I recall instance of a manager who would say "get one of the file monkeys to take this to the duper".

In tracking down leak later, it seemed that ones delivered by a certain "file monkey" always hit boards sooner (if not prior to release).

There is no assurance than the people at the duplicator won't take a copy or load one on to a thumbnail drive.  The houses do have certain security measures, but nothing is perfect.