Pontefract Castle II was captured by Henry Bolingbroke's supporters in August 1399 and initially imprisoned in the Tower of London. Sometime before Christmas that year he was moved to Pontefract Castle (via Knaresborough) where he remained under guard until his death, perhaps on 14 February 1400. William Shakespeare's play Richard III mentions this incident: Various chroniclers suggest that Richard was starved to death by his captors, and others suggest he starved himself. A contemporary French chronicler suggested that Richard II had been hacked to death, but this is, according to the ODNB, "almost certainly fictitious". In 1536, the castle's guardian, Thomas Darcy,
Pontefract Castle 1st Baron Darcy de Darcy handed over the castle to the leaders of the Pilgrimage of Grace, a Catholic rebellion from northern England against the rule of King Henry VIII. Lord Darcy was executed for this alleged "surrender," which the king viewed as an act of treason. In 1541, during a royal tour of the provinces, it was alleged that King Henry's fifth wife, Queen Catherine Howard, committed her first act of adultery with Sir Thomas Culpeper at Pontefract Castle, a crime for which she was apprehended and executed without trial. Mary, Queen of Scots was lodged at the castle