Hell, he should have just gone to the local police, told them he was homeless and wanted to go in Hawaii. Once upon a time, “progressive” localities like San Jose were giving the homeless one-way tickets to Hawaii, where they can receive about $700 a month in benefits and were allowed (at one time) to live on the beach. Give your problem to someone else.
If that program is still around, the kid could have flown in the cabin and (perhaps) convince the gate agent to upgrade him to first class.
Just did some checking...looks like Hawaii has now implemented that program in reverse; last year, they were offering one-way tickets off the islands for homeless who were living there. By some estimates there are at least 17,000 homeless in the islands, which must be a real plus for the tourism industry.