Unlike many family names whose origins owe to their ancestors trade or location, the name Moneypenny has been traced back to a single individual from whom all the current Moneypennys appear to be descended. A Richard Moneypenny (originally Dauphin) whose name (and lands) was given to him by Malcolm III of Scotland.

The family had title on land around Pitmilly, near St. Andrews, Fife, Scotland. From here the family branched to Northern Ireland during the 17th century as part of the protestant plantation. From the north of Ireland branches spread to America and elsewhere. A branch from Ulster spread to southern England around Kent. Also a Middlesex branch seems to have originated directly from the Scottish line.

The last five generations of my branch of the Moneypenny family have been born and raised in Merseyside. They all trace back to a David Moneypenny, born in Ireland in 1821, who came to Liverpool as the port expanded and jobs boomed.

There have been many spellings of the family name through the generations often seeing the name alter from one form from Grandfather to Father and back to the original again for the Son. The most common spelling currently is Moneypenny though the original Scottish line have often used Monypenny.

Burkes Peerage list the current Monypenny of Pitmully as being Peter John Gybbon Monypenny, the direct descendant of Ricardus De Moniepennie, 1st Laird of Pitmilly, granted a charter by Thomas, Prior of St Andrews, of the lands of Pitmulin ("quam Malisius tennit") 1211.

The following is taken from Chuck Moneypenny's site and tells the yarn about how the name came about. *(see note).

[According to a "Genealogy of the Name Monipennie conformably to an old MS in the time of James II of Scotland", by William Tulloch, Bishop of Moray, 1472-88, the origin of the Moneypenny is as follows - 1057. Malcolm III surnamed Canmoir, King of Scotland, being obliged to flee out of Scotland after his father was murdered by Macbeth, came into England, where he lodged with a French Gentleman named James Dauphin, a rich merchant at London, who proved to be an extraordinary friend to the King, by reason he had a fair daughter named Blanche whom the King loved. This gentleman being extremely rich and a true friend to the King, wherefore the King discovered his mind to him, and desired he would assist him with some few pennies-to which the gentleman answered in sport that it would not be a few pennies but "monie (many) pennies," but that he did what he could, these words came very true to pass afterwords. The King being resolved, went away and was accompanied with a great number of all nations, amongst the rest were this gentleman’s two sons, named Richard and Robert, and two other gentleman their good brethren one by name Hieronimus surnamed Mazvallia, son to the Lord Dalbrusko in Italia, of whom descended William de Brusko who was Chancellor of Scotland in King Alexander’s time, and many more of that name who formerly lived in this Kingdom. The other good brother named William descended of the Earl of Cherters in France of him descended all of the name of Cherters in Scotland. As for the eldest son of James Dauphin, the King gifted him the lands of Pitmilly, Kinkell, and Earlshall, and married him to a lady related to Macduff, Thane of Fife, of him descended all those of the name Monypenny, which surname the King gave him by reason of his father’s answer. His brother, Robert, was married to a lady related to Gospartrick Earl of Northumberland, of him descended all those of the name Fitz James in Dorsetshire in England."

A note adds that King Malcolm had issue by the said Blanche as follows-Airlotta, married Signet, seventh Earl of Orkney; Manifeda, married Lobie, one of the progenitors of Cambel; Maud, married Gilchrist, Earl of Angus; and Duncan, afterwords Duncan II of Scotland.

To what extent the forgoing story may be relied upon, cannot easily be determined; but that it contains something of truth is probable from the facts that a Dolphin occupies the first and fourth quarters of the Moneypenny Arms and that the name, Richard, is subsequently found in the family.

In any case, Thomas, Prior of St Andrews 1200-11, gave Richard Monipennie the lands of Pitmaulin (Pitmilly), which Malisius had held.

*Note.

It's a ripping yarn but a quick glance at the dates show it to be just that. Malcolm III's death (1093) predates the first Monipennie, Richard, by sometime as title was given to Richard in 1211. However if you substitute Malcolm for a later Canmore, William the Lion (1165-1214) who was a contemporary of Richard Monipennie, then the story becomes very plausible.

William the Lion (think of the Red Lion rampant on a yellow background - yes that William), took an army to Northumberland to capture Alnwick Castle. He was defeated and captured. He was then taken as a hostage to Normandy and had to agree to accept Henry II as overlord of Scotland. 15 years later and Richard the Lion Heart succeeded to the English throne. Richard (to raise money for the First Crusade) sold back the sovereignty of Scotland to William in 1189. To raise this money William called in every favour and loan he could get his hands on with the promise of Scottish lands in return.

So a Norman merchant financing William's return to the Scottish throne in exchange for estates for his sons suddenly fits plausibly into the story and timescale. Possibly the good bishop writing nearly 300 years after the event got his Canmores mixed up?