Pain fitzJohn (before 110010 July 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 chamberlain to King Henry, that position is not securely confirmed in contemporary records. He did hold other offices, however, 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 while 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, 1st Earl of Hereford. Pain was generous in his gifts of land to a number of monastic houses.

Family background Pain was a son, probably the eldest, of John fitzRichard, a tenant-in-chief listed in Domesday Book.Tout and Dalton "Eustace fitz John" Oxford Dictionary of National Biography 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.Remfry "Early Mortimers of Wigmore" Foundations pp. 404–406 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.Mason "Pain fitz John" Oxford Dictionary of National Biography His other siblings included William, Alice and Agnes. William was probably the same William who later held Harptree in Somerset,Keats-Rohan Domesday Descendants p. 920 and in 1130 was a royal justice in western England.Dalton "Eustace Fitz John" Speculum p. 360 Alice was the abbess of Barking Abbey and Agnes became the wife of Roger de Valognes.Keats-Rohan Domesday People p. 284

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.Dalton "Eustace Fitz John" Speculum p. 359

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,Keats-Rohan Domesday Descendants p. 919 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 Biographys designation of Sybil as Hugh's niece,Coplestone-Crow "Payn fitzJohn and Ludlow Castle" Shropshire History and Archaeology pp. 171–172 and daughter of Geoffrey Talbot and Agnes, the sister of Hugh de Lacy.Coplestone-Crow "Payn fitzJohn and Ludlow Castle" Shropshire History and Archaeology p. 179Crouch Reign of King Stephen p. 79 footnote 21

King Henry and King Stephen recognised 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.Coplestone-Crow "Payn fitzJohn and Ludlow Castle" Shropshire History and Archaeology p. 178

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.Green Henry I p. 174 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.Sanders English Baronies p. 95 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;Coplestone-Crow "Payn fitzJohn and Ludlow Castle" Shropshire History and Archaeology p. 176 his holdings of land were considered to be worth 17 knights fees.Coplestone-Crow "From Foundation to Anarchy" Ludlow Castle p. 25 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 chamberlain—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.Green Government of England pp. 30–31 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",Quoted in Dalton "Eustace Fitz John" Speculum p. 360 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.Dalton "Eustace Fitz John" Speculum p. 361

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.Green Henry I p. 133 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,Green English Sheriffs p. 45 and probably until his death. Pain is also often termed the king's "viceregent" or "justiciar" for those counties,Wightman Lacy Family pp. 178–179 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.Hollister Henry I p. 313

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 castellans".Quoted in Dalton "Eustace Fitz John" Speculum p. 359 Although Orderic stated that the families of these men were not considered high status, this was probably 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.Green Government of England p. 140 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.Hollister "Anglo-Norman Succession Debate" Journal of Medieval History pp. 30–31

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.Coplestone-Crow "From Foundation to Anarchy" Ludlow Castle p. 23 During Henry's reign, the Welsh border was a zone of frequent raids and conflict between the Anglo-Normans and the Welsh.Bartlett England Under the Norman and Angevin Kings p. 73

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.Newman Anglo-Norman Nobility p. 103 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".Quoted in Coplestone-Crow "Payn fitzJohn and Ludlow Castle" Shropshire History and Archaeology p. 179