Simon first appears during King Edward I of England's great campaign in 1277 against Llywelyn ap Gruffudd in Wales.
Simon was summoned to the parliament which met on 30 September 1283 at Shrewsbury for the trial of Llywelyn's brother, Dafydd ap Gruffydd.
In 1290 he was apparently confirmed in the possession of Shipton Montacute, Somerset and received additional grants in Dorset Devonshire, Buckinghamshire, and Oxfordshire.
On 14 June 1294, he was summoned to meet the king at Portsmouth on 1 September and accompany him to Gascony, but his services were apparently for the time dispensed with.
In 1296, however, he was in command of a vessel, and by his bravery broke through the French fleet blockading Bordeaux and revictualled the town, which caused the siege to be raised.
In 1304 Aufrica de Connoght, as an alleged heiress of the Magnús Óláfsson, King of Mann and the Isles, quitclaimed these claimed rights to Simon.
He was summoned to attend parliament at the coronation of King Edward II of England and in 1308 was made governor of Beaumaris Castle, Anglesey.