Link: Douglas

The Flemings and the Douglas family
Rivals and allies, 1340 - 1590

The Douglases were the most powerful family in southern Scotland, and the Flemings’ dealings with them swung between service, marriage and bloodshed. A Douglas sold the Flemings’ earldom, killed one Fleming chief and died alongside another.

The earldom and the killing of Sir David

In the 1340s Malcolm, 1st Earl of Wigtown, witnessed David II’s grants to William Douglas. In 1372 his grandson Thomas sold the earldom of Wigtown to Archibald Douglas, the Grim. In February 1406 Sir David Fleming was killed at Long Hermiston Muir by James Douglas of Balvenie and his men. Sir David had been granted Cavers, a former Douglas barony, only months before.

The Black Dinner

The quarrel did not prevent co-operation. In 1419 David Fleming of Boghall commanded part of the Scottish army of Sir William Douglas in France. Sir Malcolm Fleming was a close ally of the Douglas earls, and in 1440 he died for it, executed after the Black Dinner at which the young Earl of Douglas was killed. His son Robert married Janet Douglas around 1445. That same year he admitted burning the corn of the Earl of Angus, a Red Douglas, and bound himself in two thousand merks.

Against Angus

During the minority of James V the Flemings opposed Archibald Douglas, 6th Earl of Angus, who held the young king. In 1528 Malcolm, 3rd Lord Fleming, swore not to support Angus, and in 1540 he sat in the Parliament that confirmed his forfeiture. Relations recovered later in the century. In 1581 Mary Fleming married James Douglas of Drumlanrig, and in 1590 Drumlanrig stood surety for the Tweedies in their settlement with the 1st Earl of Wigtown.