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.

Although later medieval traditions described Pain as a chamberlain to King Henry, that position is not securely confirmed in contemporary records.

[9] 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.

Pain's Oxford Dictionary of National Biography entry states that he married Sybil Talbot, the niece of Hugh de Lacy.

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.

[26] Although he held the title to Weobley Castle,[23] he does not appear to have exercised any control over it, which eventually went to Gilbert de Lacy.

The story continues that Pain once drank the wine and was caught out by Henry when the king subsequently demanded his nightcap.

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.

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".

[41] 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.

[42] 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.

"[43] The later medieval writer Gerald of Wales called Miles and Pain "secretaries and privy councillors of the king".

[49] 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.

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.

[13] The king rewarded the brothers by continuing to appoint them to judicial functions, and confirmed grants made by them to various religious houses.

[56] 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.

[56][57] In 1119 Pope Callixtus 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.

[61] On 10 July 1137 Pain was killed by a javelin blow to the head[62] during an ambush by the Welsh[13][l] as he was leading a relief expedition to the garrison at Carmarthen.

[63] Pain's widow continued to hold Ludlow Castle until the middle of 1139, when she was forced to surrender it to King Stephen.

[64] 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.

[23] The king also settled the bulk of the inheritance on Cecily, which led to disturbances and a minor war among disappointed claimants.