Our story starts with Thomas Chaloner the Elder who was born in 1521. Thomas’s father, Roger, was an usher in the privy chamber of Henry VIII. Thomas was well educated and was sent off in 1540 as secretary to Sir Henry Knyvett to the court of Charles V and from there he was sent to Scotland where he was knighted after the Battle of Pinkie in 1547. He continued to serve Mary I in a diplomatic capacity before becoming Elizabeth I’s ambassador to Philip II at Brussels, although it is known that he was in England during 1560 and 1561. By then he was wealthy enough to build himself a house in Clerkenwell and he also had properties in Guisborough, St Bees and Steeple Clayton, a property in Buckinghamshire that he had been granted by Queen Mary.

From there he journeyed to Paris where he met Sir Nicholas Throckmorton, the English Ambassador to France. Unfortunately he arrived just as war broke out between the authorities and the French Huguenots. Chaloner, who despite his good relations with Mary was Protestant, was promptly arrested. When he was released, having met with Catherine de Medici and the Huguenot leaders, he made his way to Madrid, where he continued to serve Queen Elizabeth despite the fact that he hated the weather, the cost of living and the extremes of Catholic faith that he encountered. Nor did the fact that he was unmarried help with the management of his estates in England.

He had hoped to marry Elizabeth Sands who was one of the queen’s ladies but in his absence she married someone else. In 1563 he received a visit from Audrey Frodsham from Cheshire. She was 33 years old when she travelled to Spain. By the time she returned to England she was expecting Chaloner’s child. Chaloner’s brother Francis, who might reasonably have expected to inherit his brother’s wealth, would describe the boy as illegitimate. The problem was that the pair wished to marry as Protestants rather than in a Catholic Church but Chaloner was delayed by his duties, trying to negotiate the release of some English sailors, so it appears that the marriage took place after the birth of Chaoloner’s heir, which took place at the end of 1564.

Chaloner the elder’s health was not good, it seems that he may have had malaria, and he died in 1565 having made a new will ensuring that his belonging went to his son. In order to prevent his brother Francis Chaloner from contesting the will, Chaloner arranged for a group of his friends, including William Cecil, to become trustees of his estate having made provision for Audrey. he also arranged that Thomas Chaloner the Younger should be educated by Cecil.

Thomas Chaloner the Younger was tutor and friend to Robert Dudley the explorer. Like his young friend, Chaloner travelled extensively and after Dudley’s flight to Tuscany with his mistress in 1605 did his best to retrieve Dudley’s fortunes for him. He was well placed to do so, having gained a place in Queen Anne’s household. This happy circumstance derived from him having been an acknowledged part of the Earl of Essex’s circle. It was his task to manage the queen’s private estates. The king also appoint him governor of Prince Henry’s household at Oatlands. Chaloner’s reputation as a chemist and his interest in natural history were the ideal qualities in a man responsible for educating a renaissance prince. Chaloner was married twice and had eighteen children. In 1610, Chaloner became Henry’s chamberlain at St James’ Palace. As well as being a scholar, Chaloner like his father was also well informed on military and diplomatic matters.

He also identified the value of his Guisborough estates for its alum, having learned the process of its manufacture during his travels to Italy. Unfortunately his plans were ruined when the king seized the mines for the Crown. The seizure was one of the reasons that Chaloner was appointed to the role of Prince Henry’s governor – it was a sweetener for the loss of a fortune. Realistically Chaloner may have thought that his family would benefit more by their association and education alongside Henry. Unfortunately the prince died in 1612 – leaving the Chaloners out in the cold.

Two of Chaloner’s sons, James and yet another Thomas, would become regicides when, in 1649, they served on the commission that tried Charles I. James did not sign the death warrant but Thomas did. This meant that in 1660 Thomas, along with the other men who signed the document, was excluded from the act that pardoned other parliamentarians. James who was prominent in Yorkshire under the patronage of General Fairfax was arrested in 1655 for suspicion of involvement with the Sealed Knot and died prior to the Restoration. Thomas, the regicide, fled to the Low Countries, under the alias of George Saunders, where he died in 1661.

Chaloner the regicide had always had a difficult relationship with the Crown. The loss of the alum mines did not help matters, especially as Charles gave them to a syndicate of favoured courtiers. However, his religious beliefs, which were opposed to all formalised religions, and the publication of a treatise led to his arrest and subsequent flight from England in 1637. He returned home by 1644 and witnessed Laud’s trial. Nor was he a fan of the Scottish army in England during the First Civil War and he espoused the view that the king was bound by the laws created by Parliament – he was one step away from declaring the sovereignty of Parliament. He would be known for his opposition to the king and it was perhaps because of this that he retained his parliamentary seat (the Borough of Richmond) after Pride’s Purge. He was instrumental in the creation of the Commonwealth and was a key figure in the development of its trade and foreign policies. As a complete aside, the Chaloners were related by marriage to Oliver Cromwell. Thomas’s nephew Edward, was married to Anne Ingoldsby – who was one of the Protector’s cousins. Richard Ingoldsby, Chaloner’s brother-in-law, for those of you who might be interested, was another regicide but because he claimed that he was forced to sign the death warrant and because he supported General Monck, he was pardoned where other regicides were not.

Chaloner’s eldest brother William become Baronet of Guisborough in 1620. However, like his father and grandfather before him, William was well travelled and his died in Turkey the following year – meaning that the baronetcy was extinct almost before it began.