regarding "i don't know where he's gonna park that thing," a cadillac is a big car and finding parking in big cities (especially NYC) is notoriously hard. driving a big, flashy, expensive car (with a bumper sticker of osama bin ladin) and trying to park it could represent a person with a huge sense of entitlement, or an attitude of trying to go into places one doesn't normally belong-- e.g. u.s. in iraq.
regarding "i don't know where he's gonna park that thing," a cadillac is a big car and finding parking in big cities (especially NYC) is notoriously hard. driving a big, flashy, expensive car (with a bumper sticker of osama bin ladin) and trying to park it could represent a person with a huge sense of entitlement, or an attitude of trying to go into places one doesn't normally belong-- e.g. u.s. in iraq.