Ironically, while I love Unix, I have spent most of my career shepherding Windows boxes. The only real horror story I got was a new coworker (turning me from "the IT guy" into "half the IT department") who looked through the Active Directory tree and found the GPO management part had replicated the organizational structure. Since there were no GPOs at the time, he considered this wasteful and confusing, so he went and deleted it.
...
Except that what he did delete, it turned out, was the actual organizational structure of the Active Directory tree, including ALL user accounts. (It's hard to explain without visuals aids, the UI gave no indication it would delete the actual AD objects, not just the (non-existent) GPOs.)
Before long, people started calling to let us know they could no longer log into their computers or the terminal server. sigh It was a fairly stressful morning.
We really tried, for about 45 minutes, to resurrect the Active Directory tree, but it was no good (this was Windows Server 2008, so no AD Recycle Bin), so we had to restore the server from backup. I have since learnt that there is backup software that allows you to restore, say, your AD tree, or maybe even just a part of it, instead of the whole machine. Well, the backup software we had at the time suuuuucked, so not only did we have to restore the entire server, but we had to literally sit all day and watch the progress bar move at glacial speed.
In the end, we had the server up and running again, and fortunately both the company's CEO and most employees actually welcomed the opportunity to finally, FINALLY clean up their desks, something every single one of them had been delaying for a long time. And by the time we were done, I was just so exhausted I wasn't even mad at the newbie anymore.
At least we learnt from that mistake, though. Got ourselves a second domain controller, and a much better backup solution. In retrospect, I think it was probably a good thing - our boss took it with good humor, no data was lost, our backup system worked, but we also saw how badly it sucked, and the incident gave us some leverage to get the funding for said upgrades. Also, everyone had a clean desk, and since it was a Friday, a couple of coworkers decided to start their weekend early.