I was born in 1365 in Munster the third son of John de Conway a Cambro-Norman knight from Pembroke and Aiofe, daughter of a minor Irish noble. I was sent to squire in the household of Lord Fitzgerald, Earl of Desmond, where I learned to use all forms of weaponry.
The latter part of the 14th century in Ireland was a turbulent time. Irish lords had started to rebel against the Anglo- Norman lords. It was at one of these battles at Althone 1381 at the age of 16 years I earned my spurs fighting against the native Irish.
Whilst fighting a local Irish lord in Croom, I met and fell in love with Lynnette, the daughter of a prominent cloth merchant named Patrick O’Feane. I ignored my father’s wishes to marry a Norman lady and married Lynnette in a secret ceremony. My father was outraged at this disobedience and informed Lord fitzGerald of my marriage to Lynnette; I had ignored the Statute of Kilkenny 1367, which forbid marrying the Irish. So both myself and Lynnette fled Ireland to the safety of a distant relative in Pembroke.
With the help of my kin I joined the retinue of the young John Hastings, 3rd Earl of Pembroke, and made a living helping the lord settle land disputes. In 1389 I followed the young Earl to the Christmas court at Woodstock Palace held by Richard II in the hope of showing my fighting prowess. But tragedy struck and I was forced to look for another lord after the earl’s death in a joust when a lance struck him in the groin.
With my growing family we travelled north to serve Reginald deGrey, 2nd Baron of Ruthyn. I helped deGrey to enforce royal demands in the Northern March, such as calling the local nobility, gentry and their men to do Royal military service.