Lord Leicester’s Love Child: Part Two

Despite, or perhaps because of, his unfortunate birth, Sir Robert Dudley went on to have the exciting life his father might well have envied. 


As we saw in Part One of this article, Sir Robert Dudley was the illegitimate son of the Earl of Leicester, born in 1574 of an affair with Douglas Howard, sister to Charles Howard, the Lord High Admiral. Although his father never married his mother, Leicester never denied his paternity and ensured Robert was raised as befits the son of an earl.

Robert attended Christ Church, Oxford, but after matriculating, unlike other sons of aristocrats, he aspired to a real profession and took up an apprenticeship as a naval architect, a profession at which he excelled and would one day stand him in very good stead. On his father’s death in 1588, Robert inherited substantial property including Castle Kenilworth. Despite his illegitimacy, as a handsome and able young man Robert was destined to go far.

Robert’s first wife was Mary Cavendish, the sister of the explorer Thomas Cavendish, and on his brother-in-law’s death in 1593, Robert inherited two boats. Despite his youth Robert led an expedition to the West Indies where he harried Spanish shipping. He also led or financed further expeditions to Africa and the Far East. In 1597 he joined his step-brother, the Earl of Essex, and his uncle, the Lord High Admiral, in their successful attack on Cadiz and was knighted on the field. On a less successful note, he also followed the Earl of Essex into his Rebellion in 1601 and was briefly imprisoned.

Now married to his second wife Alice Leigh, and the father of five daughters, in 1603 Sir Robert initiated a lawsuit to establish his legitimacy, claiming that his parents had been secretly married before his birth. If the suit had succeeded he would have been able to claim his father’s title of Earl of Leicester and also that of his uncle of Earl of Warwick as he, too, had died without an heir. His father’s widow, Lettice Knollys, Countess of Leicester, immediately responded with a countersuit for defamation. The case was heard in the Star Chamber, was resolved in the Countess’s favour, and Sir Robert was ordered to pay a fine of £100.

Distressed at losing the case, Sir Robert angrily repudiated England and his family and ran off to France, taking with him his cousin and mistress, Elizabeth Southwell, who travelled disguised as a pageboy. There he and Elizabeth converted to Catholicism and received a Papal dispensation to marry.

Sir Robert then sought work as a naval engineer for the Grand Duke of Tuscany where he undertook several major and successful projects including draining the swamp between Pisa and Livorno so that he could build a port there, designing several new classes of warships and publishing a major work on navigation and cartography. In the meantime he was involved in protracted negotiations with King James I for his return, but when James demanded that Sir Robert should abandon his new family in favour of his English family, he finally determined not to return and his English estates were forfeit.

However, in compensation the Holy Roman Emperor, Ferdinand II, revived the defunct Dudley titles of Earl of Warwick and Duke of Northumberland so that Sir Robert was able to claim these titles within the Holy Roman Empire. He was also given a villa in Florence as a reward for his services. Throughout his life, he was consulted by the Grand Duke on all his major building works, and he served as Grand Chamberlain to three successive Grand Duchesses.

All in all, the now Duke of Northumberland and his Duchess lived happily ever after with their thirteen children who were all married into the Italian nobility.


© Pauline Montagna 2013



The Social Navigations of Sir Robert Dudley (1574–1649), a dissertation by Cory Miyuki Ota Hollis, University of California (2008) available online through Google Books.
The Tudor Place Website, biographies of the Earl of Leicester, Douglas Howard, Sir Robert Dudley

Originally published at englishhistoryauthors.blogspot.com.au on December 29, 2013.


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