On this day (-1) in 1506, one of the most famous failures in history passed into the ages.
Christopher Columbus has been celebrated for centuries as the man who discovered America, even though he did no such thing. In fact he failed spectacularly at almost everything he set out to accomplish on his voyage across the Atlantic Ocean. As one historian, Bill Bryson, has opined, "It would be hard to name any figure in history who has achieved more lasting fame with less competence."
Columbus was an Italian-born sailor with a knack for getting the opportunity to make sales pitches to European royalty. The product he was selling was his vision of a trade mission to the far east via a faster and cheaper route. After being shown the door by the King of Portugal, he was somehow able to make multiple presentations to the King and Queen of Spain, who finally bought in and sent him on his voyage to the east (by sailing west) to procure spices with which to flavor the royal treasury, if not their royal palates.
But his sailing prowess was eclipsed by his poor geographical skills and he underestimated the size of the globe by a large margin. Only about two months after setting sail he "discovered" the Orient after blundering into an island in the Caribbean. He promptly hopped ashore and claimed that everything thereabouts belonged to Spain. (Which is rather like getting out of your canoe on the opposite side of the lake and claiming you now own someone else's lake front cottage.)
A few weeks thereafter he discovered Cuba but never quite figured out that it was an island instead of a continent. He thought it was the coast of China. Soon enough he discovered Hispaniola, which he thought was probably Japan. He never even conceived of North America much less set foot upon it. To be fair, it's not his fault that people screwed up the history later on. He probably would have been shocked (and delighted) to learn how he set the stage for all that followed.
But his real failures are in what he brought back to his benefactors in Spain. You see, he wasn't much of a botanist or mineralogist either. He brought back a whole lot of good-for-nothing tree bark thinking it was cinnamon and a lot of what he thought were peppers. He was partially correct on the peppers, but it turned out they were actually chili peppers, which was somewhat of an eye opening experience for the folks back home when they first chomped down on one.
What he thought was gold was actually iron pyrite. He filled the holds with it. He also brought back some "Indian captives", which is a polite way of saying he kidnapped some local people and made them into slaves.
But back in Spain the royalty (not wanting to admit how much money they wasted on the folly) declared him a hero, gave him the title of "admiral of the ocean sea" and doubled down on their bet. They sent him back ASAP, and quite a few more times after that. He spent eight years drifting around the Caribbean screwing up one thing after another.
In all fairness, he did bring back gold on some occasions, and not everything he brought back was useless. But of all the things he brought back from the place that wasn't the Orient, the most lasting one seems to have been a gift that keeps giving, syphilis.
Source material: At Home, A Short History of Private Life by Bill Bryson.