Second hand tool nomination (last guy I flew with told me the story):
Christmas week a Falcon attempts to go VNY to OGG (Maui). Said Falcon has no HF radio. Mass confusion as ATC tries to convey to him that he needs to have a way to communicate to Oakland Oceanic. Finally another jet offers to relay position reports to ATC. Then, after all that, the guys gets about half way to the second fix on the track and decides he doesn't have the fuel to continue and wants a clearance to go to LAX. When asked if he wanted to back to VNY, he says, no, I need to go to LAX.
Sounds like the boss wanted to visit the islands for the holiday and Chippy the chief pilot said "sure" without doing a little research. It would also be interesting to see if they had rafts and vests. I'm thinking No.