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Simon Fleming of Kennethmont, son of Bertolf
(c1149 - after 1235)
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Simon, son of Bertolf, held land at Kennethmont in Aberdeenshire before moving west in the service of the Stewards of Scotland. He is the first of the family known to have been called Fleming, and through his sons Simon and Hugh he was the ancestor of the Flemings of Barochan, Dumbarton, Fulwood and Biggar.

A son of Bertolf

Simon was born around 1149, a son of the Flemish settler Bertolf, whose son Malcolm founded the Leslie family and whose son Norman was linked with Wardhouse. Simon appears in charters both as Symone Flamench, “Simon the Fleming”, and as Symone filio Bertulfi, “Simon son of Bertolf”. Together these show that the Fleming name and the descent from Bertolf belong to the same man.

Kennethmont and the Earl of Huntingdon

In the 1190s Simon owned land at Kennethmont, close to his brothers’ lands at Leslie and Wardhouse in the Garioch. He acted as a perambulator, walking and fixing the boundaries, for a charter of David, Earl of Huntingdon, to Arbroath Abbey, which his brother Malcolm also witnessed. Like his brothers, Simon witnessed other acts of the earl, including those associated with the foundation and endowment of Lindores Abbey in 1191 and 1202–1203.

In the service of the Stewards

Like Baldwin of Biggar before him, Simon served Walter fitz Alan, the first High Steward of Scotland. Between 1165 and 1177 he witnessed a charter of Walter’s wife Eschina granting land at Molla to Paisley Abbey, and decades later he witnessed Walter’s own charter granting Mow in Roxburghshire to Melrose Abbey.

Between 1208 and 1232 Simon witnessed a confirmation by Gilbert son of Henry de St Martin of two ploughgates at Penuld, modern Fulton near Johnstone in Renfrewshire, to Paisley Abbey. Fulton lies only eight kilometres from Barochan and Fulwood, the later seats of two Fleming branches.

Into the Lennox

Simon’s service to the Steward probably brought him from Aberdeenshire to the west, and into the orbit of the earls of Lennox, whose lands stretched from Loch Long around the Gare Loch and Loch Lomond to the borders of Renfrewshire and Clydesdale. Maldoven, who became 3rd Earl of Lennox in 1217, married a daughter of Walter the Steward. Beginning with Simon, successive generations of Flemings kept close links with the Lennox earls for more than a century.

Between 1208 and 1234 Simon witnessed a charter of Earl Maldoven granting lands at Luss, on Loch Lomond, to Maldoven son of Gille Muire. It was the first of many Luss transactions witnessed by Simon and his descendants. Between 1303 and 1308 his descendant Malcolm Fleming of Fulwood witnessed a later Luss charter of Earl Malcolm, a document whose misdating led earlier historians to invent an earlier Malcolm Fleming who never existed.

A long life

Simon lived to be almost ninety. On 25 April 1235 he attended, with his son Hugh, a convention between Earl Maldoven and Gilbert, son of Samuel Blackhall.

Family and legacy

Simon had two sons, both recorded as “son of Simon son of Bertolf”. Simon of Lectehtwerling was probably the founder of the Flemings of Barochan. Hugh of Dalnottar, perhaps the younger, was probably the ancestor of the Dumbarton Flemings, from whom the Fulwood, Kirkmichael and Biggar branches later came. Simon therefore stands at the head of all the main Scottish lines of the Fleming family (aside from his brother's descendants, the Flemings of Wardhouse).