My current organisation is like that
My boss stores all of his work on his laptop. The inevitable happened. Now he has to convince our IT dept to somehow rescue his files from a dead drive. It maybe possible but probably won't be cheap. I have been telling him for 8 years to store his stuff on the server but no, he knows better......
For years we stored valuable HD corporate video footage on a 2TB external hard drive because our IT dept couldn't be arsed to give us some server room to store the files. Eventually I had the CEO threaten them and all of a sudden 5TB or dedicated regularly backed up storage appeared for our dept overnight.
Two things I hate the most is when nobody listens and when I end up being right because nobody listened.