Reginald Grey, 3rd Baron Grey de Ruthyn

Reginald Grey, 3rd Baron Grey de Ruthyn (c. 1362 – 30 September 1440), a powerful Welsh marcher lord, succeeded to the title on his father's death in July 1388.

Reginald Grey was the eldest son of Reginald Grey, 2nd Baron Grey de Ruthyn and Eleanor Le Strange of Blackmere. His paternal grandparents were Roger Grey, 1st Baron Grey de Ruthyn and Elizabeth de Hastings. His maternal grandparents were John Le Strange, 2nd Baron Strange of Blackmere and Ankaret Le Botiller. His youngest sister Ida de Grey, who married Sir John Cockayne, was an ancestress of Anne and Mary Boleyn.

Grey married firstly, after 25 November 1378, Margaret de Roos (or Ros), daughter of Thomas de Ros, 4th Baron de Ros of Helmsley by Beatrice Stafford, daughter of Ralph de Stafford, 1st Earl of Stafford, by whom he had two sons and several daughters, including:

Grey married secondly on 7 February 1415, Joan de Astley, daughter of Sir William de Astley, 4th Baron Astley and Joan de Willoughby, by whom he had three sons and three daughters, including:

In 1410 after a long legal dispute, the younger Reginald won the right to bear the arms of the Hastings family, but rather than the undifferenced arms which were born by the Hastings of Sutton he won the right to the higher status quartered arms born by his deceased cousin the Earl of Pembroke: Hastings quartering Valence. Since he had gained the right to bear these arms from his claim through his paternal grandmother, he displayed Quarterly 1 & 4: Grey de Ruthyn; 2 & 3: Hastings quartering Valence. (Sir John de Grey displayed the new family arms with a label argent for difference from his father's arms). More important from a financial perspective, he gained title to certain properties of the estate.

De Grey enjoyed the favour both of Richard II and Henry IV, and his chief military exploits were against the Welsh, during the rebellion of Owain Glyndŵr.. Reynold de Grey was responsible for issuing and enforcing royal demands in the Northern March, such as calling the local nobility and gentry and their men to Royal and military service. He was already in a long-running legal dispute with Glyndŵr, claiming a tranche of Glyndwr's land as his own. Under King Richard II the case had been found in favour of Glyndŵr, but on the usurpation of King Henry IV of England Lord Grey seized the land. Early in September 1400, Henry IV left Newcastle and traveled south to Northampton, which he reached by 19th. There news reached the King of the quarrel that had broken out between Grey and Glyndwr. Grey was a member of the King's Council.

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