I've come across the answer about what it means to bleed something but am having a hard time finding its origin. What was the original thing that was bled and in what context was it used?
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Cambridge Dictionary of American Idioms explain this
This fits with the usage of "bleed something" as a negative and damaging one, and not therapeutic. This is pretty much what @Robusto's answer to your related question states.
There seems to be a good deal of confusion in the answers here, and in the answers to the older question referenced by this questioner between at least two different ways "to bleed something":
The original question was about the latter kind of usage, and as best I can tell, this question is about that also.
So, the metaphorical use of to bleed seems to stretch into the distant past. In the second kind of usage, the earliest example the Oxford English Dictionary gives is this line from Shakespeare's Winter's Tale (V. ii. 88):
I would say that it refers to the practice of blood letting using leaches. Physicians of days past, I need to find an exact time-dated reference for you, would bleed patients of "harmful humours". The idea was that blood loss would cure the patient of his ailment.
Summary, w/specific answers to your question:
Side note: This also why physicians themselves were referred to as leaches, but not in a pejorative way, i.e. connoting fee-gouging behavior.