Ashley sat in several parliaments, and was highly distinguished by favor of Queen Elizabeth I of England.

Through this marriage, Ashley greatly increased his wealth, which included the ownership of a large family manor in Wimborne St Giles, East Dorset.

Ashley thrived, expanding his land and holdings under King Henry IV of England.

In April 1596, Spanish regiments took the town of Calais from French Huguenots, which geographically offered an advantageous place from which to prepare for an invasion of the British Isles.

[2] East Dorset noblemen and regular soldiers were commissioned by the monarch to supply troops, raising their quotas by indenture from a variety of sources.

A Commission of Array was used to raise troops for a foreign expedition during this time, while various Militia Acts directed that (in theory) the entire male population who owned property and lands over a certain amount in value, was required to keep arms at home and periodically train or report to musters.

While some[4] of the 1st Earl of Shaftesbury's biographers have made the mistake of claiming that Sir Anthony Ashley served as "Secretary to the Council of War" to Queen Elizabeth, there was no such office in those days.

Sir Anthony Ashley brought charges against Meyrick of pilfering in connection with the goods captured from the enemy.

On his return home, Ashley was charged with embezzlement, was imprisoned, and lived for some time in disgrace.

Later in life, when Ashley inherited the Wimborne St Giles estate, he became a liberal benefactor of the parish.

He rebuilt the parish church, and built and endowed alms houses for the relief of eleven senior citizens.

In 1622, two years after his wife, Jane, died from smallpox, Sir Anthony married 19-year-old Philippa Sheldon.

On 3 July 1622, Sir Anthony Ashley was created 1st Baronet of Wimborne St Giles, By King James I [6] However, his liveliest interests rested in the grandchild born to inherit the ancient possessions of his house.

After Ashley died, his wife Philippa went on to marry Carew Raleigh, son of Sir Walter Raleigh, while his daughter, Anne, inherited the family estates at Wimborne St Giles, then conveyed to her husband, Sir John Cooper, 1st Baronet, of Rockbourne.

[7] Vernacular verse of the period remarked that he had “left sodomy [to] marry [Philippa] Sheldon”, and made note of his interest in his wife's "black arse hole", suggesting that any child she had would be illegitimate.