Pain fitzJohn Pain fitzJohn ( sometimes Payn fitzJohn , Payn FitzJohn , or Pagan fitzJohn ; died 1137 ) was an Anglo - Norman nobleman and administrator , one of King Henry I of England ' s " new men " , who owed their positions and wealth to the king . Pain ' s family originated in Normandy , but there is little to suggest that he had many ties there , and he appears to have spent most of his career in England and the Welsh Marches . A son of a minor nobleman , he rose through ability to become an important royal official during Henry ' s reign . In 1115 he was rewarded with marriage to an heiress , thereby gaining control of the town of Ludlow and its castle , which he augmented with further acquisitions . Although later medieval traditions described Pain as a to King Henry , that position is not securely confirmed in contemporary records . He did hold other offices though , including that of sheriff in two counties near the border between England and Wales . In his capacity as a royal justice Pain also heard legal cases for the king throughout much of western England . After King Henry ' s death in 1135 Pain supported Henry ' s nephew , King Stephen , and was with the new king throughout 1136 . In July 1137 Pain was ambushed by the Welsh and killed as he was leading a relief expedition to the garrison at Carmarthen . His heirs were his daughters , Cecily and Agnes . Cecily married the son of one of Pain ' s close associates , Miles of Gloucester . Pain was generous in his gifts of land to a number of monastic houses . Family background . Pain was a son , likely the eldest , of John fitzRichard , a tenant - in - chief listed in " Domesday Book " . John may have had two wives , therefore the identity of Pain ' s mother is uncertain . On the basis of landholding , it has been speculated that Pain ' s mother was a daughter of Ralph Mortimer , who held Wigmore in " Domesday Book " . As well as being a moneyer , Pain ' s paternal grandfather , who came from near Avranches in Normandy , owned a mill . Pain ' s brother , Eustace fitzJohn , became a royal official who owned lands in the north of England . His other siblings included William , Alice and Agnes . William was probably the same William who later held Harptree in Somerset , and in 1130 was a royal justice in western England . Alice was the abbess of Barking Abbey and Agnes became the wife of Roger de Valognes . Pain was born some time before 1100 . His father may have been in the service of King Henry in Normandy before Henry became king . The family lands in England , which were not extensive , were mainly in East Anglia , and Pain appears to have inherited most of them ; his payment for danegeld , a tax , in 1130 for his East Anglian properties was 40 shillings , compared to only 9 shillings for his brother Eustace . Marriage and lands . All accounts agree that Pain married in 1115 and that his wife was named Sybil , although the identity of Sybil ' s parents is unclear . Pain ' s " Oxford Dictionary of National Biography " entry states that he married Sybil Talbot , the niece of Hugh de Lacy . The " Complete Peerage " states that he married Sybil , the daughter of Geoffrey Talbot and Talbot ' s wife Agnes , who was herself probably the daughter of Walter de Lacy . The historian K . S . B . Keats - Rohan states that Pain married Sybil de Lacy , the daughter of Hugh de Lacy , a view shared by fellow historians Judith Green and Paul Dalton . Others such as Bruce Coplestone - Crow and David Crouch agree with the " Oxford Dictionary of National Biography " s designation of Sybil as Hugh ' s niece , and daughter of Geoffrey Talbot and Agnes , the sister of Hugh de Lacy . King Henry and King Stephen recognized Pain as the legitimate holder of the lands acquired through his wife Sybil . Her kinsman Gilbert de Lacy was the son of Roger de Lacy , who had been banished from England in 1095 and his English estates confiscated ; he had though retained his properties in Normandy . Roger ' s English possessions were given to his brother Hugh de Lacy , from whom Sybil had inherited them . On Roger ' s death Gilbert inherited the lands in Normandy , and pressed his claim to the family ' s former English estates . Coplestone - Crow speculates that the uncertainty hanging over the inheritance was one reason why Pain endeavoured to secure more lands around Ludlow . Pain is the presumed builder of Pain ' s Castle in the Welsh county of Radnor . He also controlled Caus Castle in Shropshire , and through his wife Ludlow Castle in the same county . Although he held the title to Weobley Castle , he does not appear to have exercised any control over it , which eventually went to Gilbert de Lacy . Pain was not the only recipient of Hugh de Lacy ' s lands ; some went to Jocelin de Dinan and some to Miles of Gloucester . Pain ' s share included property in Gloucestershire , Herefordshire , and Worcestershire , and he succeeded in acquiring additional lands near Ludlow , adding to the manors he held there through his wife ; his holdings of land were considered to be worth 17 knights fees . By 1130 he had evidently acquired additional properties in Oxfordshire , where he is recorded as being excused payment of danegeld that year . Career . Under Henry I . Pain was too young to serve King William Rufus , but according to the later 12th - century writings of Walter Map he may have been a — one of the officials in charge of the royal household — for William ' s brother , King Henry I ( reigned 1100 – 1135 ) . There is no contemporary evidence for Pain having held that office and nor is it likely , given Map ' s story , that Pain was involved with Henry ' s financial affairs ; rather it appears that if indeed he was a chamberlain , he was a body servant . Map relates a story about Pain serving the king personally at night , providing Henry with wine if the king called for it . The story continues that Pain once drank the wine and was caught out by Henry when the king subsequently demanded his nightcap . Map finishes the story by saying that the king then ordered that Pain should be given wine every night while awaiting the king ' s pleasure . Although the story is unlikely to be true in all details , it suggests that Pain ' s service to the king was personal as well as judicial and governmental . Other evidence against Map ' s claim that Pain was a chamberlain is that he never attested a royal charter in that office . The author of the " Gesta Stephani " described Pain as having been a page at Henry ' s court , stating that he owed his position to being one of the " special and very intimate friends of King Henry " and that although Pain had been " taken into [ Henry ' s ] service as [ one of his ] court pages " , it appears likely that the three fitzJohn brothers — Pain , Eustace and William — worked to advance each other ' s careers , as they are frequently found witnessing , or attesting , the same charters and other royal documents . In 1115 , Pain was a witness to a charter of confirmation that King Henry issued to Geoffrey de Clive , the Bishop of Hereford , issued in the Welsh Marches . Sometime between 1123 and 1127 he was appointed Sheriff of Herefordshire , and in 1127 became Sheriff of Shropshire also . He held the sheriffdoms of Hereford and Shropshire at least until 1136 , and probably until his death . Pain is also often termed the king ' s " viceregent " or " justiciar " for those counties , and he had the custody of King Henry ' s prisoner , Waleran of Melun , from September 1126 until late 1126 , when Waleran was moved to Wallingford Castle and the custody of Brian fitzCount . Pain was one of Henry ' s " new men " , who owed their positions and wealth to the king . The medieval writer Orderic Vitalis described them as a group as " of base stock who had served him [ Henry ] well , raised them , so to say , from the dust " and that the king " stationed them above earls and famous castellan s " . Although Orderic stated that the families of these men were not considered high status , this likely was an exaggeration on the chronicler ' s part . Pain ' s family was respectable enough , as his father held a number of properties directly from the king . It appears that Pain did not always take the king ' s side ; the historian C . Warren Hollister has argued that Pain was not among the supporters of Henry ' s only surviving legitimate child , Matilda , in 1126 , when Henry had his nobility swear that they would recognise her as his heiress . Hollister feels that the removal of Waleran from Pain ' s custody was a sign that Pain had not supported Matilda . Pain consolidated much of his power in Shropshire and Herefordshire at Bridgnorth Castle , often using that site as a place of business in preference to Shrewsbury , which had previously been the main centre of business for his predecessors as sheriff . As well as Waleran , Pain imprisoned a Welsh hostage there in 1128 , Llywelyn ab Owain , the nephew of Maredudd ap Bleddyn , ruler of the Welsh principality of Powys . Besides Bridgnorth , Pain used his possession of Ludlow Castle to consolidate his power in the Welsh Marches . During Henry ' s reign , the Welsh border was a zone of frequent raids and conflict between the Anglo - Normans and the Welsh . The " Gesta Stephani " indicates that Pain , along with Miles of Gloucester , was a major landholder in the western part of England , and the pair managed to dominate justice in that region . According to the document the two men " raised their power to such a pitch that from the Severn to the sea , all along the border between England and Wales , they involved everyone in litigation and forced services . " The later medieval writer Gerald of Wales called Miles and Pain " secretaries and privy councillors of the king " . The 1130 Pipe Roll noted that Pain was a royal justice in Staffordshire , Gloucestershire , and Pembroke . Besides the ordinary court , Pain also heard cases relating to the forest law in those counties . The Pipe Roll does not record Pain as sheriff in Shropshire , but this is likely due to the fact that the Shropshire returns for that year are missing from it . Also in 1130 , Pain was consulted by the king about the appointment to a vacant bishopric . The Diocese of Hereford had been vacant since the death of Richard de Capella in August 1127 , and the king consulted with Pain and the constable of Hereford before accepting their candidate — Robert de Bethune , the prior of Llanthony Priory . In 1132 Pain was present , along with his brother , at the Christmas court held by King Henry . Subsequently Caus Castle , which was under Pain ' s control , was burnt by the Welsh in 1134 . As lord of Caus , Pain was involved in efforts to suppress Welsh raiding . Although Pain held Caus , his title to the fortification was unclear , as it had earlier been held by Robert Corbet . By the end of Henry ' s reign , Pain had witnessed over 60 royal charters for the king , spanning a period from around 1115 until 1135 . Although Pain witnessed a large number of royal documents , this activity took place mostly in England , as few of the documents he witnessed were drawn up while the king was in Normandy . As a reward for his service , Henry gave Pain the lordship s of Ewias Lacy and Archenfield , both in Wales . Under Stephen . Following King Henry ' s death in 1135 , the succession was disputed between the king ' s nephews — Stephen and his elder brother , Theobald II , Count of Champagne — and Henry ' s surviving legitimate child Matilda , usually known as the Empress Matilda because of her first marriage to the Holy Roman Emperor , Henry V . King Henry ' s only legitimate son , William , had died in 1120 . After Matilda was widowed in 1125 , she returned to her father , who married her to Geoffrey , Count of Anjou . All the magnates of England and Normandy were required to declare fealty to Matilda as Henry ' s heir , but when Henry I died in 1135 , Stephen rushed to England and had himself crowned before either Theobald or Matilda could react . The Norman barons accepted Stephen as Duke of Normandy , and Theobald contented himself with his possessions in France . Matilda , though , was less sanguine , and secured the support of the Scottish king , David , who was her maternal uncle , and in 1138 also that of her half - brother , Robert , Earl of Gloucester , an illegitimate son of Henry I . On Henry ' s death in December 1135 , Pain attended the king ' s funeral . Pain was an early supporter of King Stephen , although he was said initially to have been afraid to appear at Stephen ' s court for fear of being confronted by those he had oppressed . Nevertheless Pain was with the new king by early January 1136 , when he witnessed one of Stephen ' s documents , dated to around 4 January 1136 , at Reading . By Easter , both Pain and his brother Eustace had formally submitted to the king . Pain witnessed a royal charter at Oxford in April 1136 . The king rewarded the brothers by continuing to appoint them to judicial functions , and confirmed grants made by them to various religious houses . After Henry ' s death , the Welsh attempted to drive out the Norman lords who had been extending their control into Wales during Henry ' s reign . Pain was with King Stephen at the siege of Exeter from June to August 1136 , early in the king ' s reign . Crouch argues that Stephen did not at that time trust Pain , and kept him at the siege to more easily monitor his actions , and to prevent him from defecting to Matilda ' s cause . Relations with the Church . In 1119 Pope Calixtus II addressed letters to a group of Anglo - Norman landholders in the Welsh Marches , including Pain , accusing them of having appropriated the lands of the Diocese of Llandaff and ordering their return . Pain was among a group of nobles similarly accused by Pope Honorius II in 1128 . Honorius once again ordered the nobles to restore to the Church lands they had confiscated . Pain gave lands to Llanthony Priory , helping to establish the endowment of that monastic house , although it is difficult to distinguish his gifts from those of Hugh de Lacy , as the monks of Llanthony grouped the gifts of both men together in their records . In addition Pain granted lands to Gloucester Abbey , which had benefited from the generosity of his father and brother , as did his wife Sybil , together with other grants to her uncle the abbot . She also gave to two churches in Hereford : St Peter and St Guthlac . Death and legacy . On 10 July 1137 Pain was killed by a javelin blow to the head , during an ambush by the Welsh as he was leading a relief expedition to the garrison at Carmarthen . He was buried in Gloucester Abbey , following a funeral service conducted by Robert de Bethune . A number of barons from the Welsh Marches attended , including Miles of Gloucester . Pain ' s widow continued to hold Ludlow Castle until the middle of 1139 , when she was forced to surrender it to King Stephen . Stephen then gave Sybil in marriage to Jocelin de Dinan , who consequently acquired Ludlow Castle through his new wife , setting up the background to Gilbert Lacy ' s attempts to seize Ludlow from Dinan on which the medieval Welsh romance work " Fouke le Fitz Waryn " is based . Pain ' s heirs were his two daughters , Cecily and Agnes . His heir male was his brother , Eustace fitzJohn . The two daughters were married five times in total ; Cecily married three times but failed to produce any direct heirs . Her first husband was Roger , the son of Miles of Gloucester . Pain arranged Cecily and Roger ' s marriage . The marriage contract specified that Roger would inherit all of Pain ' s lands , but as result of the latter ' s death the marriage was not contracted until December 1137 , when King Stephen confirmed the terms of the settlement . The king also settled the bulk of the inheritance on Cecily , which led to disturbances and a minor war among disappointed claimants . Agnes married Warin de Munchensy and after his death Haldenald de Bidun . She died after 1185 , by which time she was described as a widow . The historian W . E . Wrightman described Pain as a " second - class baron and first - class civil servant " .