Despite the attractive simplicity of the explanation, this name has nothing whatsoever to do with coinage and money. Eighteenth century heraldic authority, Alexander Nisbet, stated that the ancient arms of this family bore a dolphin and from this he conjectured that the Monypennys may originally have been knights from the Dauphinate region of Auvergne in France. The name Magnepenine appears in Normandy towards the end of the twelfth and the name Manipenyn is later found in English documents. In Scotland, the family acquired lands of Putmullin, later called Pitmilly, from the prior of St Andrews at the beginning of the thirteenth century. John Monipenny appears on the Ragman Roll, rendering homage for his lands to Edward I in 1296 after the devastating English invasion that year which had ousted King John. He may also be the same John Monipenny who was one of the ambassadors to Edward III of England in 1336.

The possible connection of the Monypennys with France was re-established in the fifteenth century, when William Monypenny acquired land in France and appears to have resided there for the latter part of his life. In 1447 he was granted a safe conduct to negotiate the marriage of Princess Eleanor of Scotland to the son of the king of France. He had clearly risen to prominence in his adopted country, where he was honoured with the title of ‘Baron and Lord of Conquersault’. He was sent, along with John Kennedy, Provost of St Andrews, on a long mission to Rome via Denmark and Castile. He presumably performed his tasks satisfactorily as he was created Lord Monypenny by King James II sometime prior to 1464.

The title became extinct when his son, Alexander, died without male issue. Isabel Monypenny, a daughter of the Baron of Pitmilly, was the mother of Cardinal Beaton, the last cardinal and primate of Scotland before the Reformation. The laird David Monypenny of Pitmilly was a distinguished lawyer at the turn of the nineteenth century. He became Solicitor General in 1811 and was thereafter elevated to the Bench with the title of ‘Lord Pitmilly’. The Monypennys of Pitmilly, who no longer bear the dolphin on their shield, are still prominent in Fife. Pitmilly is five miles from St Andrews. The original castle was replaced by a grand house in the eighteenth century, which was gradually extended over the following decades. The last Monypenny of Pitmilly was Charlton Monypenny, who left for South America in 1902.