Of all the epic fails in the life of Christopher Columbus, offering his services to the King of Portugal has got to be in the top five.

In 1476, Columbus found himself shipwrecked, floating by the coast of Portugal. He then spent 19 years in Portugal after marrying the daughter of a famous Atlantic Coloniser. Columbus wanted to be like his father-in-law, sailing through uncharted waters to find new lands and new slaves. Through his marriage to Felipa Moniz Perestrello, Columbus inched closer to his dream.

It's 1480, Columbus and his wife are back from their honeymoon. They go to meet Filipa’s mother in Lisbon. Columbus makes the most of it by making his mother-in-law drudge up all of his late father-in-law’s navigation stuff. He finds a lot of maps and a even more theories. Exactly what he had been looking for. With all of this ammo, he was positive he could find someone to sponsor his adventures.

The artist Daniel Nikolaus Chodowiecki is known for his apathetic treatment of historical episodes. He wasn’t very good at getting into the moment, but try he did. This etching definitely has some of the Chodowiecki humor everyone’s always talking about. Columbus looks young and hopeful, almost naive. He appears to be nervous, but also aggressive. The King, on the other hand, reclines casually, rapt with attention. The two figures are interrupted by a third, suspicious, advisor-type person. He won’t let Columbus get any closer, and he’s definitely going to advise the King against this expedition. So, who did the King listen to?

By the time Columbus approached John II in 1493, he had been practicing his open ocean navigation. Columbus made a compelling presentation: he truly believed that if they went west they would eventually find Asia. Columbus wanted this, really bad. He told John II that he would discover India and Cipangu for him. Columbus just wanted a chance to prove himself. You can see that desperation in Chodowiecki’s etching. The King of Portugal wasn’t so sure. His advisors believed that Columbus had made some errors in calculation. Nonetheless, they sent out a secret vessel to test the theory. The boat returned with absolutely nothing to report. John II denied Columbus’ application, immediately. DENIED.