Digweed hailed from Herefordshire. Many years before working for Edward, he was married with children, but following his wife's death, he left his children in the care of his sister. While working for Edward, he fell in love with Betty, the nursemaid of Edward's son Haytham.
In 1735, the Templar Reginald Birch began targeting Edward for his journal, containing his research on the Grand Temple. As Edward's gentleman, Digweed was the only one entrusted with the key to the valuables in the plate room. A mercenary with a West Country accent threatened Digweed into giving them the journal, or else they would kill his family, but Digweed did not know its location.
After Birch was given a clue to the journal's location by Haytham, mercenaries stormed the Kenway household, killing Edward, seizing the journal and kidnapping his daughter Jenny. Afterward, Digweed attended to the household, finding a new employer for Betty, before fleeing when Haytham suspected he was the traitor that Jenny screamed about before she was taken away.
In 1747, Haytham realized Betty was Digweed's lover, and intercepted a letter from her addressed to him in the Black Forest town of St. Peter, not far from Freiburg. Haytham and Birch rode there, learning Digweed lived in a cabin fifteen miles north, but Birch's mercenaries arrived beforehand to silence him.
The West Country man tied Digweed to a chair and tortured him, before fleeing when Haytham arrived. As Haytham pursued him, Birch took the opportunity to end Digweed's life, ensuring Haytham would not discover the truth.
- Digweed's first name is incorrectly listed as "Geoffrey" in the character list at the back of Forsaken.