Sir Robert Dudley was born on 7th August 1574 and was the illegitimate son of Robert Dudley, 1st Earl of Leicester and Lady Douglas Sheffield. He grew up in his father’s household and was educated at Christ Church, Oxford.
At the age of 14, in 1588, as the Spanish Armada approached England the younger Robert Dudley joined his father at Tilbury as he commanded the army. The elder Dudley would die just weeks later and left his illegitimate son a large inheritance which included Kenilworth castle and estates and upon the death of his uncle the lordships of Denbigh and Chirk.
In 1591 Dudley was contracted to marry Frances Vavasour with the consent of the Queen, however, the stipulation was that Dudley was to wait until he was slightly older as he was still 17. In the same year Frances Vavasour secretly married another man and the Queen banished her from court. Instead Dudley went on to marry Margaret Cavendish secretly and as a result also found himself banished from court, this banishment only lasted a few days before Elizabeth allowed him back to court. Margaret died soon after their marriage.
Dudley became interested in exploration and in 1594 he assembled a fleet of ships led by his galleon the Beare. Dudley intended to head towards the Spanish who were in the Atlantic and disturb them, the Queen disapproved of the plan due to Dudley’s inexperience and that the fleet was worth a lot of money eventually she agreed to Dudley being a general and sailing the Guiana instead. Dudley recruited 275 sailors along with captains Thomas Jobson and Benjamin Wood. The fleet set sail on 6th November 1594 but were delayed by storms that divided the fleet. They eventually regrouped in the Canary Islands. By December they captured two Spanish ships and incorporated them into the English fleet up until this point it looked as if the expedition would be a failure. From Tenerife the fleet sailed towards Cabo Blanco and then on towards Trinidad where Dudley discovered an island that he claimed in the name of the Queen and called Dudleiana. The fleet recruited a Spanish speaking Indian to guide then in search of Gold but the guide deserted them and the fleet had to find their own way back to the meeting point. In March 1595 Dudley led the fleet north towards Cabo Rojo, Puerto Rico before sailing towards Bermuda. With the fleet low on provisions and ammunition as well as no sign of any Spanish Dudley began leading the fleet home to England. It was travelling to England that they engaged in a two day battle with a Spanish ship, although they won the battle they did not capture the ship and landed back in Cornwall in May 1595.
The following year, in 1596, Dudley joined Robert Devereux, 2nd Earl of Essex, in an expedition against Cadiz where he was knighted for his conduct during the Capture of Cadiz.
Also in 1596 Dudley married Alice Leigh and the couple went on to have seven daughters.
In 1603 Dudley was informed by a traveller, Thomas Drury, that his parents had secretly married and that Dudley was the legitimate son of his father. This began a case that appeared in front of the Star Chamber in 1604 to legitimise his claims and allow himself to be called the Earl of Leicester and Earl of Warwick. Over 90 witnesses appeared on behalf of Dudley who even had his own mother write that the marriage happened although she could not remember the details including the date or who conducted the ceremony. On the other side of the argument Lettice Knollys, Robert Dudley’s widow called 57 witnesses to deny the claims that were being put forward. As a result the Star Chamber declared that the marriage never happened and Dudley was not only illegitimate but deceived by Thomas Drury.
In 1605 Dudley left his wife and fled England with Elizabeth Southwell, his mistress and cousin after declaring that they had converted to Roman Catholicism. They found themselves in Lyon in 1606 where after receiving a papal dispensation married. The newlyweds headed to Florence where they would set up their new life together. After arriving in Florence, Dudley began calling himself the Earl of Leicester and the Earl of Warwick, titles that were denied to him by the Star Chamber. The couple would go on to have 13 children together, many of whom married into Italian families.
Dudley became a naval advisor to Ferdinand I, Grand Duke of Tuscany and set about designing and building war ships for the Tuscan navy.
In 1607 King James I ordered Dudley to come back to England and provide for his estranged wife and family, the King even revoked Dudley’s travel permit to force him to return, however, Dudley refused and remained on the continent. As a result the King confiscated Dudley’s estates and declared him an outlaw. Although the King had outlawed him, his son the Prince of Wales, remained in touch with Dudley and negotiated the sale of Kenilworth Castle. In 1611 a price of £14,500 was agreed upon with Dudley keeping the position of constable of the castle, the young Prince died the year later and Dudley had only received £3000 of the agreed fee. Kenilworth Castle became the property of the new Prince of Wales, Charles. Charles only paid £4000 for the property after he passed an Act of Parliament in 1621 that allowed Dudley’s estranged wife to negotiate the sale of the property.
In 1644 King Charles I created Dudley’s deserted wife a Duchess in her own right and recognised Dudley’s claims to legitimacy. Although he was now legitimate the King did not grant Dudley the titles or estates that belonged to his father.
Robert Dudley died on 6th September 1649 in Villa Rinieri and was buried at San Pancrazio in Florence. Dudley left his entire estate to Ferdinand II de’Medici, Grand Duke of Tuscany.
A portrait believed to be Sir Robert Dudley