Exploring The Many Lives Of An Infamous Cumbrian Woman With ‘Who Was Ann Gregg?’

Many people have family stories, legends or myths that have there origins lost in history.

This was the case with David Holmes.

As a young man he traveled the country and regaled his adventures to his Grandmother, who told him, “You’ve got too much gypsy blood in you! You should settle down!”

This comment stayed with David as he started researching his family tree some years later and went looking for the truth of his Grandmother’s comment.

What started out as a hunt for the origin of the saying turned into an investigation into British crime and punishment, occupations and culture in Cumbria.

Taking us back thorough the ages to when we transported criminals to America and had the death penalty for theft, David made it back to his five-times great grandmother Ann Gregg.

What followed would be worthy of any Sherlock Holmes novel or Who Do You Think You Are? episode as the twists and turns, highs and lows left you in disbelief.

Using newspaper and court records David managed to piece together the story of Ann Gregg, who turned out to be a career criminal with many aliases.

Adding historical context to the unbelievable tale such as the daring raid on Whitehaven by John Paul Jones or explanation of place names like Rosley only brings the colourful characters to life in greater detail as they are placed on streets we still walk today.

Who Was Ann Gregg? is like an iceberg of Cumbrian history as with each turn more was unraveled from below the depths.