Rapscallion is such a delightfully mischievous word. The very feel of it rolling off your tongue embodies what it represents. When I first picked the word to be etymologized, I had a sneaking suspicion that it was related to rascal. In fact, it's a 1690 alteration of rascallion, which in turn is universally described as a "fanciful elaboration" of rascal. The p just makes it swankier. As for rascal itself, it's been around English since the early fourteenth century. In Middle English, it was rascaile, which meant "lower class" (based on a connection rich people made between poverty and lawlessness). In Old French it was it was rascaille, which had more of a connotation of "outcast", and here it gets really interesting. This could be from rasque, or "filth", which really does even more to reflect on how the poor were perceived back then. If true, rasque could then be traced to Latin raiscere, meaning "to scrape" (because you scrape off filth, or in this case, the outcasts from society)
Adam Aleksic, a rising sophomore studying linguistics and government at Harvard University, has been described as the internet's sixth most famous etymologist. He also has disturbing interests in politics, vexillology, geography, board games, conlanging, and law.