In several raids in 1307 and 1308 James Douglas provided support to King Robert in the south of Scotland. On the night of Tuesday 19 February 1314 James Douglas and his men wearing black coats to cover their armor attacked Roxbrugh Castle. Roxbrugh was the main English stronghold in south central Scotland. It was defended by 100 English soldiers. The fall of Roxbrugh Castle caused many in the area to flee back to England. Now held by Douglas it was the beginning of his reputation as "the Black Douglas". To the people of Scotland he was the "the Good Sir James". He was now one of the king's greatest supporter and a model of chivalry. But James had black hair and a reputation so feared by the English they named him "the Black Douglas." They said his evil success against them was because he was a demon himself. His son and grandson also used the feared name themselves continuing the family reputation.