How does anyone know this sort of thing of giving outsiders access to administrator accounts has not gone on since Wikipedia's beginning? CheckUsers have better things to do than check every single editor with administrator functions or higher all the time and even CU is "not magic pixie dust," as Wikipedians say.
I doubt that it has gone on since Wikipedia's beginning. nobody would have bothered in the early days. Still, it has doubtless happened a few times. I agree that it is often very difficult to detect, and there would frequently be "false positives", when an admin moved or switched ISPs for example. But any strange behavior by an admin is usually enough to set alarm bells ringing.