For one of them I got a t-shirt from Shark Tank! But I'm not going to write about that one, it'd take too long.
Boss 1 (very early '90s): we're holding a rare all-hands meeting on a Thursday or Friday (small dept, 8 people or so, tops), and I'm starting a two week vacation that weekend. Whole purpose of the meeting was for Boss to say that when I get back from vacation, I'll no longer be the LAN admin, I'm going to work with Bob doing COBOL programming, and Dave is going to take over as LAN admin for Finance. I came within an inch of saying 'Fuck you, Larry, I quit. I'll be in tomorrow to clean out my desk.' Larry hadn't said a word to me in advance about this change, never a whisper of it. While I could do COBOL, I much preferred doing FoxPro and managing the LAN. And I knew Dave couldn't handle doing everything for Finance. Over my vacation I thought about it and I decided to wait it out. I started showing Dave everything that I did for Finance, and he was quickly lost. Nothing further was discussed, nothing changed, and I never wrote a line of code with Bob. And people in Finance wept when I left because they knew they were now at the tender mercies of Larry.
Boss 2, which predated Larry. I had been hired (mid '80s) to create a merge document in a word processing package for creating retirement plan contracts. Awesome job, got me out of a lousy job. Eventually that job transitioned to running the billing system, maintaining the PCs, etc. It then evolved to create a reporting system in dBase III for the canned accounting package to produce better and prettier reports. My boss, the office manager, hired her husband to come in as Senior IT, and he clearly had little knowledge of micros. Eventually my boss told me that I was being put back in to doing word processing, which led me to find another job. One of the programs that I'd written was for producing 1099 forms as they were required whenever a pension plan did a distribution. Okidata Microline 93 printer, continuous form feed of multi-part pre-printed forms, dBase III (boss's hubby wouldn't let me use FoxPro because 'I might get hit by a bus'), and some very specific formatting code like microline advance to make the database info line up with the pre-printed form. In the code were comments that said "DO NOT ADJUST THE CODE IN THIS BLOCK OR YOU'LL BREAK THE FORMATTING!" You couldn't miss it. He touched the code, apparently didn't have a backup, broke the code, and they were never able to print the forms again.
Boss 3 (actually management above my boss was the problem): Working at a school, appeared to be a good job, I'd spent over two years developing a very nice database system for them. It was complete, worked great, just needed final deployment. Costs for software and hardware had already been paid. Everyone there is on an annual contract: all teachers, all staff. Then the administration decided not to renew my contract. Zero complaints about my work, excellent reviews, never called in to an office to discuss something bad that I'd done, and the project was complete. The project was never deployed: complete waste of time and money. At least I got to mothball it so that it could be brought back with a few weeks work if a more intelligent type of administrator is found (highly unlikely). They later told my boss that I had been hired on a temporary basis for the project. Funny how the fact that it was a temporary role was never mentioned in my interview. Or on-boarding process. Or annual review. Or contract renewal. Or to either of my bosses (the one who hired me retired a year later).
Boss 4. Working for a moderately-sized city. The storage admin, who 'knew all', didn't want me backing up the ERP system (180 gig or so a that time, growing at about 5% per month) using SQL Server's transaction log and database backups. He said the SAN backups would capture it all. Finally a meeting was called with Boss, SAN admin, and me. I lost, and I turned off SQL Server backups on that instance as instructed. Later, after I was gone, the IT manager (or maybe HR, they were a bunch of 'special' people) decided they didn't need a DBA and would let a vendor monitor their databases. On a different database that came along after I'd left, with billable data, they didn't notice that the backups had stopped working. They didn't notice that the database consistency checks had started reporting corruption in the database. And then the SAN developed a glitch that caused occasional drives to drop out. Eventually one of those drops hit the database being monitored by the vendor, and it blew sky high. And it was unrecoverable because of the failed backups and corruption. They found a restorable copy, but it was a couple of months old, so they lost lots of billable information that could not be recreated. No, they don't need a DBA! As far as I know, no one was disciplined for losing that data.
Boss 5. Working for a major city. Classic case of 'Take credit for everything good that IT does, blame everyone when something bad happens.' After I left, I found out that IT was becoming a hell hole because of her. Eventually she was told by the city manager: 'Resign or face prosecution.' Apparently she'd screwed over one of her underlings over FMLA and had exposed the city to tremendous liability. She quit.