In the 18th and 19th century, thievery was prevalent in the Wild West. Freight companies often used teams of horses or donkeys to move goods from town to town. Marauding thieves would often target these mule and horse teams for their valuable cargo--including salt, hematite and sometimes raw beef.

Any 5 year old knows that trying to stop a 16 mule team at a full gallop, dead in its tracks is not only impossible, but also dangerous. One runs the risk of being trampled or even eaten alive, limb by limb. So, to bring these pachyderms to a stop, bandits would dig trenches 20 feet deep and 30 feet long then cover the trench with sticks and stones and weed and bombs. The mule team would unsuspectingly go galloping over the covered trench and to their dismay, would fall in and all of the horses and mules would perish. The cargo, however, would remain intact and it was then simply a matter of the thieves lower themselves into the pit to reap the reward of raw beef and hematite from the corpses of the mules.

These pits soon became known as assholes, as the primary type of animal that would become ensnared were mules and donkeys. As rail and steam ships became more common for transporting goods, the "asshole" fell out of popularity. The true meaning of the word became diluted over time and eventually came to mean 'a dishonest or thieving person who does not have the best intentions for others.'

Your current boss.

someone being arrogant, rude, obnoxious, or just a total dickhead....

Your butt hole. Were your shit comes out.

A person in another car who cuts you off to get to the next lane, almost hits you while talking on the phone.

An obnoxious, arrogant, self-centered male who women can't seem to get enough of.

Anyone who doesn't do exactly what you think they ought to do, exactly when you think they ought to do it.

The worst kind of person. You cannot fully construct a meaning that fully encompasses what this vicious insult means. If you're an asshole, you are disgusting, loathesome, vile, distasteful, wrathful, belligerent, agoraphobic, and more. Assholes are human fecal matter. They are the lowest of the low. They transcend all forms of immorality. It is the very worst of insults; to be called an asshole is to have your very soul ripped apart and shat on. I say that the word "asshole" is the worst cussword of the english language, worst than fuck, shit, and cunt combined.