How easy would it be for a Google/ISP insider to become the ultimate extortionist?

The Google thread I started in GD got me thinking: with the right access, a Google employee could find out enough about the lives of powerful (or even average) people to become a modern day Charles Augustus Milverton (Sherlock Holmes, by the way), collect awesome amounts of money and power (assuming this person was tech savvy and smart enough not to get caught, but that’s outside the purview of this post). Obviously, potential victims wouldn’t use Google for the REALLY bad stuff, so I’d also like to consider ISPs in this question.

How easy would doing so be? Who has the kind of access necessary? I assume that there’s a system set up to set off red flags for below a certain level of employee, not to mention internal logs, but could it be done by anyone but the CEO or similar level?

Send $1billion dollars to this address or I will inform the media you googled “chance of HIV from anal sex”. Or that someone from your IP really likes obese midget porn?

Would that really work in reality? Who would bother complying?

Well, once you know what you’re looking for, actual evidence becomes easier to find, you know?