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O'Leary is and always has been essentially a Co, Cork surname. like many Gaelic septs they were driven from their original habitat at the time of the Anglo-Saxon invasion at the end of the twelfth century, but they did not migrate far - only from Corea Laoidhe in the south-west of Cork to Inchigeela in the same county, a remote territory with the lofty Kerry mountains insight to the west of them. Here they long ruled as Chiefs under the paramount Muskerry MacCarthys.
Out of one hundred and three landowners recorded in the civil survey (1654) of the Barony of Muskerry no less that thirty four were O'Learys, while MacCarhtys numbered forty one and O'herlihys ten. The name is today very numerous being sixty second in the list of hundred commonest names in Ireland with an estimated population figure of almost ten thousand persons. It is remarkable, what a large portion of these, as indicated by vital statistics, were born in that part of the country to which the sept traditionally belongs -no-less than eighty per cent.
In this connection it may be added that there are two places called Ballyleary in Ireland, Both in Co. Cork.
The O'Learys took a prominent part in the Irish Wars against the English Invader when these affected Munster. They suffered much in the Desmond Wars; one Mahon O'Leary was a forerunner of the 'Wild Geese' as he went to Spain with d'Aquila after Kinsale; fifteen were attained in 1642; the name is found in the 1691 attainders and also in the Irish regiments of France in the eighteenth century.
Indeed almost every aspect of Irish Life has been enriched by an O'Leary. Literature has Ellen O'Leary (1839-1889), a patriotic poetress, Joseph O'Leary (1795-1855), song writer and, most notable of all Father Peter O'Leary (1839-1919), better known as Peadar O'Laoghaire, called in his day "the greatest living of the Irish (Gaelic) prose". Law has Joseph O'Leary (1792-1857), author of many standard legal works; William Hegarty O'Leary (1836-1880) made his name as a surgeon; while the most famous of all was John O'Leary (1830-1907), the Fenian. In the field of athletics Daniel O'Leary(1846-1933) performed amazing feats in America and held the world record for long distance walking.
The town of Dunlaoghaire, formally Dunleary, a suburb of Dublin, is named after Laoghaire who was King of Ireland at the time of St Patrick in the fifth century; but this of course has no connection with the surname formed some six centuries later.
In the Irish language O'Leary is O'Laoghaire.