My dad has a funny story about one of his previous jobs. It was a very Corporate job, involved lots of business trips and business dinners. The company’s policy was essentially that your direct supervisor was the one who approved all business expenses. Well, my dad’s direct supervisor at the time was a guy who he had become quite good friends with. They frequently were going on trips/dinners together, so my dad’s supervisor made him a deal. Anytime they were out together, my dad was the one who paid for everything; and in exchange, his supervisor promised to always approve his expense reports (because if the supervisor had paid, then it would have been *his* supervisor checking the reports, which I guess had the potential they wouldn’t be approved?).
My dad said there were a couple times where it was, like, thousands of dollars, and he was legit worried that it would be beyond the pale, in spite of their deal.
But every single one got approved… ;-p