Sir Reginald Crawford of Loudoun, 5th Sheriff of Ayr

On 14 May 1296, the English administration appointed him as Sheriff of Ayr by the English administration.[1] In June 1297, he was one of several Scots nobles who did a deal where the English released them to fight against Andrew Moray.[2] This suggests that he may have participated in the revolt in early 1297, which ended in the capitulation at Irvine.
He supported Robert the Bruce and was captured during the Battle of Loch Ryan in February 1307. He was executed by hanging in Carlisle, England.

https://books.google.com/books?id=L3NEAQAAMAAJ&pg=PA700&dq=reginald...

One of the first of the Scottish barons to join William Wallace, his cousin; he was executed at Carlisle, February 13, 1307.

Sheriff of Ayr 1296