There are many Irish surnames of multiple spellings, but this one goes far beyond the normal range. Recorded in the spellings of McAnaney, McAnany, McAnanny, McAneaney, McAneeny, McAneny, McAnneny, McEnenie, McEneny, McNeeney, McNenny, and many, many, more spellings the 'correct' form is MacEnenay, and this is now, according to the famous irish etymologist Edward Lysaght, almost extinct. It is said that it derives from the ancient pre 11th century gaelic 'Mac an Deaganaigh', which is believed to translate as 'The descendant of the son of the little Dean', presumably a reference to a member of the church. As the clergy have been expected to be celibate since the 10th century, when the pope decreed that they were devoting too much time to their wives and not enough to the church business, 'dean' must have some meaning outside the church. Either way there were originally two separate clans, one in County Roscommon, where a place called Limacanneny may have been the original homelands, the other in County Monaghan. The name is one of the earliest of proven Irish surnames (see below), the nameholders being 'Coarbs', i.e. hereditary lords of the church, and another example being John MacAneaney of Clogher in 1398. It is said that there are at least forty two different ways of spelling the name, and it is claimed that the tombstones of one family in Toronto record the name in six different spellings! The first recorded spelling of the family name is shown to be that of John MacAneany, which was dated 1365, coarb of St Tighearnach of Clones, Ireland, during the reign of King Edward 111 of England, 1327 - 1377. Surnames became necessary when governments introduced personal taxation. In England this was known as Poll Tax. Throughout the centuries, surnames in every country have continued to "develop" often leading to astonishing variants of the original spelling.

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