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The earliest Tudors can be traced to an area known as the Four Cantrels, which eventually became the lordship of Denbigh in North Wales. The family began as landowners, and when the area became controlled by Llywelyn ab Iorwerth - "the Great" (d. 1240) some family members entered the service of the Prince.

Ednyfed Fychan (d. 1246) was a servant to Llywelyn from 1215 to 1240 and for a large part of the time was lord steward to the Prince (one of the most important offices in the administration). In his capacity as steward, Ednyfed represented his Prince in negotiations with Henry III, King of England, as well as other lords and princes.

Ednyfed married Gwenllian, daughter of Lord Rhys. They had six or seven sons, each of which followed their father into the service of the Princes of Gwynedd. Goronwy ab Ednyfed (son of Ednyfed), became steward to Llywelyn the Last by 1258. After Goronwy's death, his brother Tudur ab Ednyfed became steward (even after he had pledged an oath of fealty to the English King Henry III and spent time in exile). Because of their service to the Welsh princes, the family gained land and became some of the wealthiest in North Wales.

Edward I succeeded as King of England in 1272 and became intent on conquering Wales. Edward had great success in his first war against Llywelyn ap Gruffydd (later to be called 'the Last'). The descendants of Ednyfed probably saw that there would be more to gain from making peace with the English king. Llywelyn the Last was killed in 1282 and Edward I took control of North Wales. Because they had sworn loyalty to Edward, some members of the family of Ednyfed Fychan were able to retain their influence.

Some of the family members, namely Tudur Hen (or 'the Elder') and Goronwy ap Goronwy, joined the rebellion of Madog ap Llywelyn. The revolts failed and the remaining family members swore their allegiance to Edward I. The king's son, Edward of Caernarfon, became the first English Prince of Wales in 1301. Tudur Hen swore loyalty to this new Prince. When Tudur died in 1311, his large land holdings passed to his son Goronwy ap Tudur, who died in 1331 in the reign of Edward III.

Goronwy ap Tudur had two sons: Hywel, who gained position in the Church as a canon of Bangor Cathedral and later Archdeacon of Anglesey; the other son was Tudur, who was influential in his part of North Wales.

Tudur ap Goronwy had five sons: Goronwy, Ednyfed, Rhys, Gwilym and Maredudd. All held important positions in North Wales, several holding positions as bailiff. Maredudd also attained the title of burgess in Newborough, a part of Anglesey. These brothers were loyal servants of Richard II and Rhys and Gwilym accompanied the king on his campaign in Ireland.

The Rebellion of Owain Glyndwr

When Richard II was deposed in 1399, he was succeeded by Henry IV. Ednyfed and Goronwy ap Tudur had drowned in 1382, so they were not faced with the problem of the remaining brothers when, in 1400, a Welsh rebellion began against the English King.

The cousin of Tudur's remaining sons was the Welsh rebel leader of renown: Owain Glyndwr. Rhys, Gwilym and Maredudd decided to support the rebellion against King Henry IV who has deposed their patron, Richard II. The rebellion collapsed, as did the family's power and influence in North Wales. All three brothers were outlawed in 1406.

There are various accounts of Rhys' death: one states that he was captured and executed in 1412; another states he died at his home in Anglesey. Gwilym ap Tudur was pardoned in 1413. Maredudd ap Tudur's final fate is unclear. But, we know that he married a lady named Marged (Margaret) and had at least one child, named Owen.