Creative Debt Solutions

When people come up short on their bill payments, they turn to all manner of schemes for quick cash: pawning a family heirloom on a reality TV show, manufacturing and selling methamphetamine, or selling some organs on the black market.  Charles I of Spain didn't have any of those options available in 1528 when he found himself unable to repay loans from the wealthy Welser family of Augsburg, so he came up with a different solution - he signed over the entirety of Venezuela.

At the time, Venezuela was an entirely unexplored jungle, filled with inhabitants who were not keen on having their land taken over by men from across the ocean in payment for someone else's debt.  A huge amount of money and effort would need to be poured into subduing the natives and building colonies before any value could be derived from the venture.  Given this, Charles' offer would seem to be less of a payment and more of an imposition.

However, that calculation fails to account for the most important fact about Venezuela: it's home to the great city of gold that would later come to be known as El Dorado.  The Welsers  spent much of their time in Venezuela (or "Klein-Venedig" as they called it) outfitting expeditions to find the city, as doing so was the only hope they had of not losing even more money on the project that was supposed to be a loan repayment.

They sent multiple poorly-planned expeditions to the interior, which wandered around the jungle for years, being slowly whittled down by the heat, unfriendly natives, hunger, difficult terrain, disease and mutiny.  The expeditions invariably returned empty-handed, with only a small fraction of their initial men.

As the Welser forces became depleted from this fruitless treasure hunting, the Spanish were able to re-assert control of the colony, eventually revoking the Welsers' charter and executing Bartholomew VI Welser.  The Welsers are estimated to have spent 3 million florins (about $600 million in modern money) on their efforts in Venezuela, and the all they got was malaria and a decapitation.