Is the person on the award ticket traveling to a funeral (or some other obviously vital purpose)?
Is there an opportunity to offer a voluntary bump to other passengers?
If not,then the J passenger should fly, if only because he is the most valuable client for the airline.
But this interesting case study shows the importance of discretion and common sense on the part of front line airline staff -- and the need for the airline to train staffers in how to exercise this discretion wisely.