Reginald Grey of Ruthin

Reginald Grey's land dispute with a Welsh neighbour turned into a fifteen-year national revolt. He was the third Baron Grey de Ruthyn, a marcher lord with substantial holdings in Denbighshire and the friendship of Henry IV, who had just taken the throne from Richard II. The quarrel was over a stretch of common land at Croesau that Grey had seized from Owain Glyndwr; when Glyndwr petitioned parliament, it was dismissed with the remark that nobody need care for barefoot Welsh dogs. Grey then compounded it by delaying the delivery of a royal summons for Glyndwr to serve in Scotland until it was too late to comply, which made him look like a traitor to the king. In September 1400 Glyndwr's followers proclaimed him Prince of Wales and burned Ruthin. The rising spread across Wales, drew in the Percys and a French expeditionary force, and took the English crown until 1415 to suppress. Grey himself was captured in 1402 at Ruthin and held for eleven months, and Glyndwr set his ransom at ten thousand marks - a sum so large that Grey mortgaged and sold land to raise it and left his heirs in debt. He gave hostages, including his eldest son, and swore not to fight the Welsh again. He kept the oath and spent the rest of his life recovering financially. He died in 1440, having outlived Glyndwr by more than twenty years. He fought at Shrewsbury in 1403 on the king's side after his release. The ransom is among the largest recorded for an English baron in that period. His descendants held Ruthin for another century.

• Lived: 1362 CE – 1440 CE
• Nationality: English
• Roles: military, politician