He knows Obama will give him the money, our money. When the Crime Syndicate (Democrats) are in charge, they will freely give our money away to anyone.
That was my first thought - in any sane universe, his request would be laughed at - in Dictator Obama’s world, next thing we know we’ll be on the hook for Cuban reparations!
I believe that Obama as one of his final acts will return Guantanamo to Cuba with the excuse that the 99 year lease has expired