Llywelyn ap Gruffudd (died 11 December 1282) or Llywelyn the Last was Prince of Gwynedd from 1255 to 1282. After successful campaigns across Wales in 1257, Llywelyn proclaimed himself Prince of Wales in 1258, and was recognised as such by Henry III of England in 1267 as part of the Treaty of Montgomery. He remained in this position until his death in an ambush at Cilmeri in 1282, one of the final events in Edward I’s conquest of Wales.
Llywelyn was the second of the four sons of Gruffudd ap Llywelyn ap Iorwerth, the eldest son of Llywelyn ab Iorwerth, and Senana ferch Caradog, the daughter of Caradoc ap Thomas ap Rhodri, Lord of Anglesey.
The eldest was Owain Goch ap Gruffudd and there were two younger brothers, Dafydd ap Gruffydd and Rhodri ap Gruffudd. He is first heard of holding lands in the Vale of Clwyd around 1244.
Following his grandfather's death in 1240, Llywelyn's uncle, Dafydd ap Llywelyn (who was Llywelyn the Great's eldest legitimate son), succeeded him as ruler of Gwynedd. At this time, Llywelyn went on crusade with Richard of Cornwall, brother of Henry III of England.
Llywelyn's father, Gruffudd (who was Llywelyn's eldest son but illegitimate), and his brother, Owain, were initially kept prisoner by Dafydd, then transferred into the custody of King Henry III of England. Gruffudd died in 1244 from a fall while trying to escape from his cell at the top of the Tower of London. The window from which he attempted to escape the Tower was bricked up and can still be seen to this day. As King Henry could no longer use Gruffudd against him, war broke out between Dafydd II and King Henry in 1245. Llywelyn supported his uncle in the savage fighting that followed. Owain, meanwhile, was freed by Henry III after his father's death and was given a portion of Snowdonia (Eryri) by Henry at the treaty of Woodstock in 1247.
Llywelyn and Owain came to terms with King Henry III and in 1247 signed the Treaty of Woodstock at Woodstock Palace. The terms they were forced to accept restricted them to the west of Conwy (Gwynedd Uwch Conwy) around Snowdonia and Anglesey, which was divided between them. The other half of Gwynedd east of Conwy known as the Perfeddwlad was taken over by King Henry.
When Dafydd ap Gruffydd came of age, King Henry accepted his homage and announced his intention to give him part of the already reduced Gwynedd. Llywelyn refused to accept this and Owain and Dafydd formed an alliance against him. This led to the Battle of Bryn Derwin in June 1255. Llywelyn defeated Owain and Dafydd and captured them, thereby becoming the sole ruler of Gwynedd Uwch Conwy. Llywelyn now looked to expand his area of control. The population of Gwynedd Is Conwy resented English rule. This area, also known as "Perfeddwlad" (meaning "middle land") had been given by King Henry to his son Edward and during the summer of 1256, he visited the area but failed to deal with grievances against the rule of his officers. An appeal was made to Llywelyn, who, that November, crossed the River Conwy with an army, accompanied by his brother, Dafydd, whom he had released from prison. By early December, Llywelyn controlled all of Gwynedd Is Conwy, apart from the royal castle at Dyserth, as a reward for his support and dispossessing his brother-in-law, Rhys Fychan, who supported the king. An English army led by Stephen Bauzan invaded to try to restore Rhys Fychan but was decisively defeated by Welsh forces at the Battle of Cadfan in June 1257, with Rhys having previously slipped away to make his peace with Llywelyn.
During 1257, Llywelyn aggressively pursued his interests and gained control of lands in Gwrtheyrnion, driving out his cousin, the Anglo-Norman, Roger Mortimer. Then to Powys, which affected his fellow Welshman, Gwenwynwyn, and Deheubarth in South Wales, helping his kin against Norman control going as far as the Bristol Channel, leaving a trail of destruction during the time of Lent. Despite liberating his fellow Welsh folk, some would return to siding with the English upon his departure. The English retaliated by mobilising a force from Scotland to Deganwy in Wales but did not cross into Conwy, which was officially Llywelyn's Welsh territory. Henry III waited for an Irish naval force to attack on land from the west to corner Llywelyn, however, his force never arrived. The acts of aggression were followed by a peace truce for 1258, of which the Marcher Lords, did not completely abide by.
The leader of Deheubarth, Rhys Fychan now accepted Llywelyn as overlord, but this caused problems for Llywelyn, as Rhys's lands had already been given to Maredudd. Llywelyn restored his lands to Rhys, but the king's envoys approached Maredudd and offered him Rhys's lands if he would change sides. Maredudd paid homage to Henry in late 1257. After the betrayal, in 1259, Llywelyn jailed Maredudd until Christmas in Criccieth Castle. Maredudd was released only for him to surrender a son as hostage, it was then Dinefwr became a vassal kingdom of Gwynedd.
In early 1258, Llywelyn was using the title Prince of Wales, first used in an agreement between Llywelyn and his supporters and the Scottish nobility associated with the Comyn family. The English Crown refused to recognise this title however, and, in 1263, Llywelyn's brother, Dafydd was hostile against the Prince and submitted himself to King Henry.
Then in January 1260, Llywelyn pursued his interests internally by dislodging Roger Mortimer of Buellt. This would be an act of war which would be followed by an English decree which was summoned in Oxford on 1 August. Armies assembled at Shrewsbury and Chester with the sole purpose of removing Llywelyn from power. However, the English could not come to an agreement in government over the matter, and a truce was enacted again for a further 2 years. After 2 years the English continued castle building which caused a revolt from the Welsh, who in turn requested and were assisted by Llywelyn in defending their lands in Maelienydd. After, Llywelyn continued his expansion into South Wales to the Lordship of Brecon, where he received fealty from the Welsh who too ousted their Anglo-Norman Marcher Lord Mortimer. This success brought him to the attention of the Montfort family, which would start a new era for Gwynedd and Llywelyn. The change in territory forced Edward I to return to Wales for the first time since 1254.
On 12 December 1263, in the commote of Ystumanner, Gruffydd ap Gwenwynwyn (Mathrafal, Powys Wenwynwyn) did homage and swore fealty to Llywelyn. In return he was made a vassal lord and the lands taken from him by Llywelyn about six years earlier were restored to him.
Llywelyn's interests were now not solely excluded to Wales. In England, Simon de Montfort (the Younger) defeated the king's supporters at the Battle of Lewes in 1264 (Second Barons' War), capturing the king and Lord Edward. Llywelyn began negotiations with de Montfort, and in 1265, offered him 25,000 marks in exchange for a permanent peace, 5,000 of which immediately and then 3,000 a year thereafter. The Treaty of Pipton, 22 June 1265, established an alliance between Llywelyn and de Montfort, although Pope Clement IV warned Llywelyn against allying himself with the excommunicated Montfort. As well as the rule of the whole Principality, Llywelyn was offered the castles of Maud, Hawarden, Ellesmere and Montgomery. Thus, Llywelyn's right to rule the Principality of Wales as the hereditary Prince of Wales would be acknowledged. De Montfort was to die at the Battle of Evesham in 1265, a battle in which Llywelyn took no part.
After Simon de Montfort's death, Llywelyn launched a campaign in order to rapidly gain a bargaining position before King Henry had fully recovered. In 1265, he routed the combined armies of Hamo le Strange and Maurice FitzGerald in North Wales. Llywelyn then moved on to Montgomery, and routed Roger Mortimer's army. With these victories and the backing of the papal legate, Ottobuono, Llywelyn opened negotiations with the king and was eventually recognised as Prince of Wales by King Henry in the Treaty of Montgomery in 1267. All of the Welsh princes submitted to Llywelyn II except for Maredudd ap Rhys Gryg. For this recognition he would have to pay the English crown 24,000 marks in installments, this agreement was confirmed by the papacy in Rome. If he wished, Llywelyn could purchase the homage of the one outstanding native prince – Maredudd ap Rhys of Deheubarth – for 5,000 marks. However, Llywelyn's territorial ambitions gradually made him unpopular with some minor Welsh leaders, particularly the princes of South Wales.