Alexander Douglass of Lynn, Capt. Samuel Douglass, and Phineas Douglass

[Robert Battle]

Alexander Douglass of Lynn, Massachusetts (originally Alastair MacDougall of Scotland) was taken prisoner in the 1650 Battle of Dunbar and sent to Massachusetts as an indentured servant. He left many Douglass descendants in New England and elsewhere, including Capt. Samuel Douglass of Mass. and N.H. and his brother Phineas Douglass. The first half of my article on this family was just published in the New England Historical and Genealogical Register; please let me know if you would like a copy!

[William Douglas]

Yes please!
I have messaged you

William

[William Douglas]

I am co-incidently looking at Douglas events involving the MacDougalls.

The clash between the MacDougalls of Argyll and the Black Douglases in the 14th century sits right at the heart of Scotland’s Wars of Independence: a collision of loyalties, geography, and personal vendettas that shaped the political map of the west and the Borders.

The MacDougalls backed the Comyn–Balliol faction and the English Crown, while the Black Douglases were the fiercest allies of Robert the Bruce. That alignment made confrontation almost inevitable.

- Clan MacDougall was a major Argyll power with strong ties to the Comyns, Bruce’s greatest rivals. Their chiefs held Dunollie and Dunstaffnage and were deeply embedded in the western seaboard power structure.
- The Black Douglas line, led in this period by Sir James Douglas, was Bruce’s most trusted lieutenant. To the Scots he was “Good Sir James”; to the English, “the Black Douglas,” a name born of fear.

When Robert the Bruce killed John Comyn in 1306, the MacDougalls—Comyn allies—became immediate enemies of Bruce and, by extension, of the Douglases who fought for him. This set the stage for a west-coast civil war within the wider struggle for independence.

Shortly after Bruce’s coronation, the MacDougalls ambushed him at Dalrigh near Tyndrum. Bruce’s forces were badly mauled, and the MacDougalls captured the famous “Brooch of Lorn,” a symbol of their victory and enduring enmity.

Bruce returned to Argyll with a vengeance. At the Pass of Brander, he crushed the MacDougalls and broke their regional power. This defeat forced the clan into exile or submission and opened the west to Bruce’s consolidation.

While Bruce subdued Argyll, James Douglas became the terror of English garrisons in the Borders. His guerrilla tactics, night raids, and relentless pressure earned him the “Black Douglas” reputation among the English.
This rise in Douglas prestige contrasted sharply with the MacDougalls’ decline.

It was not a feud of equals: the MacDougalls were a great Argyll house undone by their political alignment; the Black Douglases were a rising Lowland power whose fortunes were tied to Bruce’s success.

Their conflict symbolised the fracturing of Scotland during the Wars of Independence—where clan loyalties, marriage alliances, and regional rivalries could be as decisive as English armies.

The MacDougall defeat helped secure Bruce’s control of the western seaboard, while the Douglases became indispensable to his military strategy and later one of the most powerful families in Scotland.

By the mid‑14th century, the MacDougalls had lost much of their former influence, while the Black Douglases were approaching the height of their power—territories stretching from the Borders to the north, wealth, castles, and a reputation that made kings uneasy.