Here's an article I found interesting. One of the many reasons American Airlines is in financial trouble — above and beyond the fact that it's become a pretty bad airline — is that they sold these "lifetime" passes to a lot of people. Travellers paid a few hundred thousand for "fly anywhere whenever you want" privileges, then took trips that priced per flight would have cost millions.
Not covered in the piece is a question I have: Did these passholders ever have to fly on some other airline? American doesn't fly to every city. Did the lifetime passengers ever have to go out and buy tickets on some other carrier? Or did they just decide to never travel to places not reachable on American? It would have felt weird after flying for "free" (or what felt like free) on American and being treated like royalty there to have to pay and get in line like all the peons on Southwest.