Re: Looper - Grade, Review, Discuss, ect.
For the sake of brevity I didn't feel like listing all the plot holes.
But that is a valid one. He's bankrupt, no passport, in another country, and tries to enter an American City that is in lock down.
"Savor the fruit of life, my young friends. It has a sweet taste when it's fresh from the vine. But don't live too long... The taste turns bitter... after a time."