[1] It is thought that Ó Rathaille was born in Screathan an Mhil (Scrahanaveal), Gneeveguilla, in the Sliabh Luachra region of County Kerry, into a relatively prosperous family.
He acquired an excellent education in the bardic school of the MacEgan family (ollamhs to the Mac Cárthaigh Mór)[3] and was taught Latin and English as well as Irish literature and history.
[3] Ó Rathaille lived through a time of major political and social upheaval in Ireland which was ultimately to result in the crushing of the Irish language and the death of the bardic tradition.
The changes in Irish society directly impacted Ó Rathaille's life and resulted in his social status being reduced from that of a respected ollamh to a destitute pauper.
Under his management, two ruthless and greed-driven men, Timothy Cronin and Murtagh Griffin, collected the hearth money tax from tenants and felled the woods for quick profit.
It is likely that as a consequence of the loss of the estate by the Brownes, Ó Rathaille had to leave his native district and lived in poverty close by Tonn Tóime, at the edge of Castlemaine Harbour, some 12 miles west of Killarney.
Having been destitute for so long (even composing a poem on his gratitude at receiving the gift of a pair of shoes) Ó Rathaille clearly hoped for a restoration of his position as ollamh, and celebrated Valentine's marriage to Honora Butler in 1720 in an Epithalamium.
It seems that the refusal of this request was sufficiently devastating for Ó Rathaille to compose the poem in which he launches a vitriolic attack on the new English gentry like Valentine Browne and makes reference to the failure of the Jacobites as being a primary cause for his own situation.
This style of poetry became a standard in Ireland, where it was dangerous to speak overtly of politics, but a poem disguised as a love song could reveal the singer's and listeners' true feelings.