the problem is that if he has to do ALL THAT he will probably not be able to check in at all

lets see

he has 1:25 minutes to do all that

clear immigration.........if he gets lucky and there is no line at all ...say 10 minutes

10 mins waiting for luggage

5 mins going through the xray machine and getting outside

5 mins more going upstairs and getting back to the terminal

10 mins paying tax

by that time he has 45 minutes and supposedly the flight will be closed as international flights leaving to the US must be totally 'done' 1 hour (I think it is) to be able to submit the manifest info to the US using the APIS system