Lord of Biggar
As a young man, Malcolm Fleming of Biggar would not have expected to become chief of Clan Fleming. While his grandfather Robert was chief when Malcolm was a toddler, the leadership then went to his uncle Malcolm Fleming of Fulwood until Malcolm of Biggar was in his thirties when his cousin Thomas Fleming of Fulwood (who was about the same age) succeeded to the role. He would have expected that future chiefs would come from Thomas' descendants.
Malcolm inherited the lands at Biggar from his father, Patrick Fleming, and the lands at Oliver Castle from his mother Joan, heiress to her father Sir Simon Fraser.
Years of war
Soon after he entered his twenties the Second War of Scottish Independence broke out after Edward Baillol led an English-backed invasion of Scotland. Balliol, the son of former Scottish king John Balliol, was attempting to make good his claim to the Scottish throne (despite the fact that his claim was void because his father had abdicated). Young Malcolm Fleming fought with the armies that defended the reign of King David II. Despite outnumbering Baillol's forces, the Scottish loyalists lost the Battle of Dupplin Moor on 11 August 1332 and Baillol was crowned king. Within three months David's partisans had regrouped and forced Balliol out of Scotland.
But these were just the opening skirmishes in a war that continued for more than 25 years, most of Malcolm's adult life. Both he and his uncle Malcolm were captured at the Battle of Neville's Cross near Durham when an invading Scottish army of 12,000 led by King David II was defeated with heavy loss by an English army of approximately 6,000–7,000 men. King David was also captured by the English and remained a prisoner for 11 years.
The Black Death
His uncle, Malcolm Fleming of Fulwood gave him land at Achmoir, Seymoir and others in 1357 just before voting in the Scottish Parliament to pay a huge ransom for the release of King David. His uncle also gave him control of his lands at Lenzie in 1361 and, in his uncle's footsteps, he was appointed Sheriff of Dunbartonshire and Governor of Dunbarton Castle in 1364. This was highly unusual because, in the ordinary course of events, these posts should have gone to his cousin (Thomas Fleming of Fulwood) who was now clan chief. Clearly Malcolm was considered by those in power to be far more capable than Thomas.
During his governorship of the castle, the most devastating plague in history (The Black Death) swept through the garrison, killing a third of the soldiers. It is estimated to have killed between 75 million and 200 million people worldwide.
He took over the mortgage (and ownership) of Lenzie from his cousin, Thomas Fleming (2nd Earl of Wigtown) in 1372 and was appointed as High Sheriff of Edinburgh and Governor of Edinburgh Castle in 1374.
4th clan chief
Malcolm was nearing 70 years old when his predecessor Thomas Fleming died and he became 4th clan chief. He inherited a mess, but immediately set about resurrecting the family's fortunes during the short time he had left.
Malcolm Fleming had survived both of the long wars of Scottish Independence as well as the devastation of The Black Death. His younger son (Patrick Fleming, 1330 – 1410) was the progenitor of the Flemings of Bord. Malcolm’s heir was his older son, David.