There are a lot of things Jesus says in the Bible that do not make immediate sense to a modern reader. Typically, it is possible to explain things things simply by saying, "At the time, things were like such and such, and people generally believed such and such." Something that has been gnawing at my brain lately is possibly one of the oddest things that he says: "It is easier for a camel to go through the eye of a needle, than for a rich man to enter into the kingdom of God." (Matthew 19:24)
This is the only passage I know of that requires an elaborate story to explain it, and usually that story is about a gate in a city wall that was called "the eye of the needle," and in order for a camel to go through it, you had to unload everything off the camel. There are also stories about a mountain pass where something similar was required. I've come to believe that this is all bunk, though. Admittedly, I don't have many reliable sources (there are these two pages that look straight out of 1998, and a Wikipedia article that needs a lot of work), but I've never heard of a reliable source for the traditional explanation, either.
One of the first problems is that there is nothing about the supposed gate or the mountain pass that is contemporary with or before Jesus. Furthermore, when he said the quotation, he was on the coast of Judea, and not near any city gates. In a time when some people never traveled outside the city they were born in, it wouldn't make sense for him to refer to something that some in his audience might never have seen.
The more likely explanation is that this is a persistent mistranslation: the Aramaic word for camel, gamla, is also the word for "rope," and context generally determines what the word is supposed to mean. If you are talking about riding through the desert on a gamla, you are probably talking about a camel. If you are talking about putting a gamla through the eye of a needle, you are probably talking about a rope.
To me, this recalls the scene in "The Life of Brian," where Brian and his mother are at the Sermon on the Mount, way at the back, and it's hard for them to understand the words. Jesus says, "Blessed are the peacemakers," and Brian's mother says, "Blessed are the cheesemakers?" Let's imagine for a moment that what ended up getting written in the Bible was, "Blessed are the cheesemakers, for they shall be called the children of God." We would have all sorts of explanations for this that involved some kind of way in which people at the time made cheese, or something else about the profession of cheesemaking.
There might not be a solid case for the Aramaic explanation, but at the very least I would like it if Biblical scholarship eventually set the record straight on which explanations are flat out false, as the traditional one seems to be. I have no hope for this though. The main reason is that the "camel" reading let's people tell a story and show off something they know. The bigger reason, though, is that there are plenty of other ways in which people are just plain terrible at reading the Bible. Many books have been written about the things that get taken out of context, or ignored, or outright fabricated. Reading the word as "camel" is fairly benign in comparison to rapture madness, or scaring people with visions of Hell.
As a side note, one of the articles linked above provides an additional explanation that is suggested by a passage in the Babylonian Talmud. A rabbi is talking about the nature of dreams, and that they will only show us that which is natural or possible: "They do not show a man a palm tree of gold, nor an elephant going through the eye of a needle." There is at least one other passage where this is used as an example of something that is not possible. So, there is a chance that Jesus was simply using "camel through the eye of a needle" as an example of something that is flatly impossible, and by saying this was easier than a rich man entering heaven, he was saying it was even less possible.
The Talmud, however, was composed well after the time when Jesus was alive, so it isn't something that could have influenced him. He was also fond of making hyperbolic comparisons, such as in the passage where he says, "Before you try to remove the mote from your brother's eye, first remove the beam from your own eye."