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Birth:          1362 of Ruthin, Denbighshire, Wales
Death:          30 Sep 1440 

Notes
https://en.wikipedia.org/wiki/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.
Lineage[edit]

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.[citation needed]

Marriages and issue[edit]

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:[1]
Thomas Grey (living 1387).[1]
Sir John Grey, eldest surviving son,[1] (c. 1387 – 1439), who predeceased his father. 
He married Constance Holland, the daughter of Elizabeth Plantagenet and John 
Holland, 1st Duke of Exeter by whom he had issue.
Margaret Grey[1] (d. aft. May 1426), who married William Bonville, 1st Baron Bonville. 
These were the great-grandparents of wealthy heiress Cecily Bonville, 7th Baroness 
Harington who married Thomas Grey, 1st Marquess of Dorset, a descendant of 
Reginald Grey by his second marriage.[2]
Catherine Grey (b. 1392), married George Lucy, Baron Lucy.
Eleanor Grey, who married Robert Poynings, 4th Baron Poynings, by whom she had 
three sons, Sir Richard Poynings (d. 10 June 1429), Sir Robert Poynings and Edward 
Poynings (d. 1484).[1] [3]

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:
Sir Edward Grey (c. 1415/1416 - 18 December 1457),[citation needed] who married 
Elizabeth Ferrers, 6th Baroness Ferrers of Groby, and had five children including Sir 
John Grey of Groby, the first husband of Elizabeth Woodville.[citation needed]
Robert Grey (born 1419), who married Eleanor Lowe.[4]
John Grey of Kempston, Bedfordshire.[4]
Constance Grey, who married Sir John Cressy.[1]
Elizabeth Grey, who married Sir William Calthorpe, by whom she had issue.[4]
Eleanor Grey, who married William Lucy, esquire, of Charlecote, Warwickshire.[4]
Alice Grey, married Sir John Knivett, a descendant of Sir John Knyvett

Rebellion of Owain Glyndwr[edit]

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 Glyndwr.. 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 Glyndwr, claiming a 
tranche of Glyndwr's land as his own. Under King Richard II the case had been found 
in favour of Glyndwr, 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.[5]

Glyndwr responded in law early in 1400 but his case was not granted a hearing, 
instead it was asked of Glyndwr that he grant Lord Grey further concessions. De Grey 
also delayed summoning Glyndwr's quota or levy of men for service in Scotland until 
the last moment, making it impossible for Glyndwr to respond as requested or even 
send an explanation for his absence and the lack of his levy. Such an act as refusal 
or failure to respond to an order of the King was deemed a treasonous act. Glyndwr's 
estates were deemed forfeit until he could prove his loyalty or receive due 
punishment. On 16 September Owain and brothers had taken up arms and burned 
Grey's property, for three days the Welsh band ravaged the countryside of Flintshire 
and Denbighshire.[5] On 24 September, Glyndwr's forces were encircled at Welshpool 
and defeated.[5]

De Grey now invited Glyndwr to a reconciliation meeting, but arrived with a large 
force, attempting to surround Glyndwr and making his intentions clear. Glyndwr 
escaped with his life and went into hiding, confirming himself a traitor in English eyes. 
King Henry confiscated the estates of Glyndwr's supporters, and granted them to John 
Beaufort, his half-brother. The rebellion spread after initial successes for the Welsh 
and by 1402 it was gathering momentum. Lord Grey was captured by Glyndwr's forces 
in an ambush near Ruthin in January.[5]

A ransom of 10,000 marks was asked for him and Lord Grey was asked to swear an 
oath never to bear arms against Glyndwr again. King Henry IV sent eleven knights to 
treat with Glyndwr and then complied with the ransom, ordering the selling of a manor 
in Kent to raise the monies in mid 1402. On 22 June, Glyndwr had captured another 
important hostage, Edmund Mortimer.[6]

Lord Grey then would have been expected to repay the amount over time as best he 
could and any outstanding debt would be borne by his family. In August, Glyndwr went 
south into the Marches. The King however held Grey in better view than Mortimer, 
whom he considered a troublemaker. While Grey and Earl of Northumberland were 
loyal; it was clear that Hotspur intended to join Glyndwr's rebellion.[5]

Hotspur had refused to surrender the Scots prisoner, earl of Douglas to the King, and 
had demanded that Edmund Mortimer be purchased his freedom. Henry was furious 
that his power should be challenged in this way.[5] The King wrote to Grey and other 
leading nobles on 23 November 1409, demanding that all officers who were entreating 
with Glyndwr should cease forthwith. The rebellion had failed after the re-capture of 
Harlech, and release of Mortimer's family. The Grey family did in fact sell the Ruthin 
Lordship to King Henry VII in 1508 when their fortunes and favour had declined.[2]

Hundred Years War[edit]

Grey was a member of the Council which governed England during the absence of 
Henry V in France in 1415; he later fought against the French in the Hundred Years 
War in 1420 and 1421. He had been previously a Governor of Ireland.

Parents
DE GREY Reginald (Reynold) (1323 - 4 Aug 1388)
LE STRANGE Alianore (Eleanore) (ABT 1331 - 20 Apr 1396)

Siblings
DE GREY Reginald (Reynold) (1362 - 30 Sep 1440)

Marriage To DE ROS Margaret (ABT 1361 - BEF 1414)
    m. AFT 25 Nov 1378 

Notes

Parents
DE ROS Thomas (13 Jan 1336 - 8 Jun 1384)
DE STAFFORD Beatrice (ABT 1340 - )

Children by DE ROS Margaret ABT 1361 - BEF 1414
GREY Elizabeth (Eleanor) (ABT 1382 - BEF 1434)

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