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Newport had a population of between 1,500 and 2,000 in the Middle Ages, a relatively normal size for a Welsh town in this period. Robert Fitzhamon died in 1107, later his daughter Mabel, married Robert, 1st Earl of Gloucester, the illegitimate son of King Henry I of England. He built the first stone keep in newport Castle, and he used it to imprison Robert II, Duke of Normandy from 1126 until his death in 1134, by order of King Henry I, who was the Duke's younger brother. During the same period Ralph "Prepositus de Kardi" ("Provost of newport") took up office as the first Mayor of newport. During this period after the Noman conquest they usually referred the leading figure by the Latin name of prepositus (English: provost) meaning "leading man". Robert (Earl of Gloucester) died in 1147 and was succeeded by his son William, 2nd Earl of Gloucester who died without male heir in 1183. The lordship of newport then passed to Prince John, later King John through his marriage to Isabel, Countess of Gloucester, William's daughter. John divorced Isabel but retained the lordship until her second marriage; to Geoffrey FitzGeoffrey de Mandeville, 2nd Earl of Essex in 1214 until 1216 when the lordship passed to Gilbert de Clare, 5th Earl of Hertford.
Between 1158 and 1316 newport was attacked on several occasions. Amongst the various attackers of the castle were Ifor Bach, who captured the Earl of Gloucester who at the time held the castle. Morgan ap Maredudd apparently attacked the settlement during the revolt of Madog ap Llywelyn in 1294. In 1316 Llywelyn Bren, Ifor Bach's great-grandson, also attacked newport Castle as part of a revolt. He was illegally executed in the town in 1318 on the order of Hugh Despenser the Younger.
By the end of the 13th century, newport was the only town in Wales with a population exceeding 2,000, but it was relatively small compared to most other notable towns in the Kingdom of England. newport had an established port in the Middle Ages and by 1327, it was declared a Staple port. The town had weekly markets and after 1340, newport also had 2 annual fairs, which drew traders from all around Glamorgan.
In 1404, Owain Glyndŵr burned newport and took newport Castle. As the town was still very small, most of the buildings were made of wood and the town was reduced to ashes. However, the town was rebuilt not long after and began to flourish once again.
The settlement of 'Newport' is first mentioned as novo burgus established by Robert, Earl of Gloucester in 1126. The name was derived from the original Latin name Novus Burgus, meaning new borough or new town. The city can sometimes be found labelled as Newport-on-Usk on old maps. The original Welsh language name for the city, Casnewydd-ar-Wysg (pronounced [kas n w ð ar w sk]) means 'New castle-on-Usk' (this is a shortened version of Castell Newydd ar Wysg) and this refers to the twelfth-century castle ruins near Newport city centre. The original Newport Castle was a small Motte-and-bailey castle in the park opposite Newport Cathedral. It was buried in rubble excavated from the Hillfield railway tunnels that were dug under Stow Hill in the 1840s and no part of it is currently visible.
Around the settlement, the new town grew to become Newport, obtaining its first charter in 1314 and was granted a second one, by Hugh Stafford, 2nd Earl of Stafford in 1385. In the 14th century friars came to Newport where they built an isolation hospital for infectious diseases. After its closure the hospital lived on in the place name "Spitty Fields" (a corruption of ysbyty, the Welsh for hospital). "Austin Friars" also remains a street name in the city.