Early life
David Fleming’s very name is indicative of the close relationship between the Fleming family and the Scottish royal family. He was probably named in honour of the king, David II.
Davey inherited the family lands at Biggar, Cumbernauld, Lenzie and Oliver Castle from his father. He married firstly Jean, only daughter of Sir David Barclay of Brechin and they had two daughters. He married secondly Isabel Strathechin, heiress of Monycabock in Aberdeenshire. They had two sons: his heir Malcolm Fleming and David Fleming who became the progenitor of the Flemings of Boghall.
Davey was probably only a boy when King David II died childless in 1371 and was succeeded on the throne by his nephew, Robert II. The son of Walter Stewart, 6th High Steward of Scotland, and Marjorie, daughter of King Robert the Bruce, he was the first monarch of the House of Stewart.
Machinations by the Earl of Carrick
The new king moved quickly to regain land that had been lost to England, but he ultimately proved to be a weak king and was usurped by his eldest son, the Earl of Carrick, in 1384. While Robert remained king, Carrick exercised the real power as the appointed Lieutenant of Scotland.
In 1388, Scotland had a victory over the English at the Battle of Otterburn, but Carrick’s ally James, Earl Douglas, was killed. Around this time, Carrick was badly injured when kicked by a horse. His younger brother, Robert Stewart, took the opportunity to increase his influence.
Machinations by Robert Stewart
Carrick’s brother, Robert Stewart, was a ruthless politician and never ceased to manipulate events towards getting himself onto the throne. In the meantime, he was the High Chamberlain of Scotland (controlling the purse strings) and Davey Fleming was his deputy.
With his brother Carrick weakened by his injury and the death of his ally Douglas, Robert Stewart persuaded the nobles to transfer the lieutenancy to himself at the expense of Carrick.
A new king
Two years later Robert II died and the weakened Carrick ascended the throne as Robert III. But the real power remained with his younger brother Robert Stewart who was still Lieutenant of Scotland, king in all but name.
When the lieutenancy expired in 1393, Robert III was reinstated. He was soon forced to concede a new lieutenancy, but he nevertheless managed to thwart his brother by installing his own son and heir, David Duke of Rothesay, to this role.
Duke of Albany
Robert Stewart remained a powerful figure, however, pulling strings in the background. In fact, he increased his power and prestige in 1398 when he had himself made Duke of Albany. David Fleming remained his deputy as High Chamberlain of Scotland and Fleming's son Malcolm was married to Albany's daughter, Elizabeth Stewart.
Rothesay, started to assert himself as best he could. For example, he arranged a marriage to a daughter of the powerful Earl of Douglas. Now, there were two factions in the Douglas family too: the Black Douglases and the Red Douglases. While the Black Douglases were allied with the king and his heir (Rothesay), the Red Douglases led by Archibald Douglas (Earl of Galloway) were allied with Albany. It had been a Red Douglas that had forced David Fleming’s cousin Thomas Fleming into selling the lands and Earlship of Wigton 28 years earlier. The Red Douglases were Fleming enemies!
David Fleming may have supplied the information that Albany used in 1401 to accuse Rothesay of misappropriating crown revenues. It may have been this controversy that led to Fleming being appointed as Auditor of Accounts in Exchequer in 1403.
When Rothesay’s tenure as Lieutenant of Scotland expired in 1402, his uncle Albany immediately arrested him and imprisoned him in Albany’s castle at Falkland where Rothesay mysteriously died soon after. Albany came under suspicion but was cleared by the General Council of Scotland. The only impediment now remaining between Albany and the throne was his other nephew, the king’s surviving son, 7-year-old James Stewart.
Ambassador to England
During the next few years, Davey Fleming was thrust into the difficult politics of the relationship between Scotland and England. He was a Commissioner charged with hammering out a truce with England on 6 July 1404. This success strengthened the hand of King Robert III and, with the aid of his close counsellors Henry Sinclair (Earl of Orkney), Henry Wardlaw and Davey Fleming he was able to reassert himself for a time. Davey Fleming was sent to England as ambassador in both 1405 and 1406.