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Matthew Whaley was the son of James Whaley and Mary Page Whaley. The portrait descended in the Jaquelin-Ambler family. According to family tradition, Mary Whaley left the portrait to the Jaquelin family. Matthew Whaley was a cousin of the Jaquelin family. This could be a member of the Jacquelin, Brodnax, or Ambler family.
The subject wears a brown jacket and green waistcoat with a silver trimmed hat under his left arm. He stands outdoors. A sword is on his left hip.