sure you can make that type of bet... but to catch your friend in a lie inquire about the following...
the money to make the bet, did...
he carry it in a paper bag or suitcase?
or did he write a check?
credit card?
marker?
if it was cash, any questions from behind the desk? did he carry all that on the plane with him? if so why? with the forfeiture laws why risk carrying any more than $1000 on you? If a Local sheriff sees that much cash he is gonna take it assuming it's drug money.
is it possible to get down that type of action? SURE
is it possible that your friend did? ????