I've been at $company for nearly ten years. This is somewhat strange for this particular industry (Tribal Gaming) as usually people get fed up with management, fed up with the pay(1), or just want a change of scenery.
I think the worst WTFery I've seen was last summer. We had seen a couple incidents of Cryptolocker poking around, and I had taken initiative to lock things down via a group policy so that I didn't have to spend several hours every couple days restoring department shares because some turkey borked their machine.
The CIO commended me for doing this. My direct boss forced me to undo those changes a few days later because I 'didn't perform a full risk assessment of the effects of locking down the machine's ability to install harmful software.'(2)
The fecal matter hit the fan shortly thereafter which ended with the CIO ordering me to re-implement my changes after a final infection damaged one of the front of line applications and took it offline for several hours before a weekend.(3)
Haven't seen a single instance of cryptolocker affecting the systems since.
1. The company has a *lot* of cash for buying pretty shiny hardware; not so much for retaining the talent to drive it.
2. Boss's way of saying "You didn't say 'mother may I' before taking steps to maintain system integrity", the buttplug.(4)
3. I don't *think* that final incident cost us any revenue, but it gave the boss a nice black eye.
4. And that's being insulting to all buttplugs. At least those don't drive people to mental breakdowns in front of their co-workers.