What is loaded out the caboose?

1) A way of saying someone is 'loaded out the butt'.

2) rich, wealthy, well-to-do, high net worth.

rich, wealthy, high net worth, upwardly mobile, super rich, 1%, wall street, tech industry, elite, baller, player

My neighbor must be loaded out the caboose. He drives a Porsche, just put in a new pool and recently got back from a Fiji.

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loaded out the caboose - video