Not working in IT, but have seen a few IT related shitshows at work.
Bosses relative of some sort working as an assistant IT guy, a dumbass 20ish kid with less actual tech knowledge than your average granny. Managed to infect the whole network with viruses from some torrented game once. Also was too lazy to walk down the hall and bring an extension cable when setting up workstations in a freshly renovated office and ran a cable at ankle height across the aisle between cubicles, with predictable results. They got rid of him after a month or so.
Owners wife (different place) hired as an assistant manager or something, a turbobitch who did nothing useful but relished in pissing everybody off. IT guy quit on spot after a particularly nasty spat, told the bitch to stuff his owned wages up her ass, literally pulled the power plug on server and walked out, also turning off his cellphone. I got two free days out of this, until the company finally managed to find someone to crack the passwords and get the system back online.
Yet another different place, the IT Dept consisted of two undergrad IT students who were hired because they were the cheapest. They usually started swilling beer at about 10 am, and were passed out at about 2pm, along with several temporary hired who used their office as a watering hole. Elaborate schemes were in order at 5pm every day to find enough sober drivers and get everybody home. Quit this one myself, so don't know what became about it eventually.