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How many English spelling anomalies occur in native Anglo-Saxon words?
This is difficult to answer. The English spelling system is complex because the spelling patterns come from Anglo-Saxon (Old English), from Latin and Greek, and from other modern languages (like French). It has been estimated that about 85 percent of the 30,000 Anglo-Saxon words died out after the onslaught of the Scandinavians and Normans, which means that only about 4,500 Old English words survived. Yet, among those surviving words are some of the most fundamental words in English: and, at, brother, but, child, drink, eat, fight, for, house, in, live, love, man, on, sister, sleep, to, and wife. According to the book The Story of English (McCrum, Robert, New York: Viking, 1986), every one of the 100 most common words in English is Anglo-Saxon. Many of our irregular or odd spellings (words such as come, do, woman) are Anglo-Saxon words that have been around so long that they are no longer pronounced the way they are spelled. English spelling anomalies often come in "families" and one of the most vexing of these for the learner is the -ough group. Say these words: bough, rough, through, cough, dough, and you will see that not one of these words sounds like any of the others. These are all native Anglo-Saxon words, not products of foreign borrowings. Another "family" is the differently pronounced homograph pairs, e.g., wind, wound, tear, sow, row, lead. Again, these are all native Anglo-Saxon words. (Other such "families" are words containing -ight and words with silent letters.) It seems that a plurality, maybe even a majority, of English spelling anomalies occur in native Anglo-Saxon words.