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Sir Henry Sidney – Lord Deputy of Ireland (1565-1578)

The boy king Edward VI, Sidney’s childhood friend, from a portrait I saw at Hever Castle in England.

Flodden to Penshurst


Sir Henry’s father William Sidney was one of Henry VIII’s courtiers, born in 1482 and knighted after the battle of Flodden in 1513. Sir William married to Anne Pagenham and his son Henry was born on 20th July 1529, at a time when the kingdom of England was on the verge of a major religious upheaval. Henry was 8 years old when, in 1537, Queen Jane Seymour presented King Henry with his long awaited male heir, the future Edward VI. Sir William Sidney was soon appointed the young Prince’s tutor while Lady Anne became his Governess.

Edward ascended the throne on his father’s death in 1547 and Sir William was appointed his Steward. In 1552, the 15 year old King granted the elderly Sir William the estate of Penshurst Place, just north west of Tunbridge Wells in Kent as a token of his esteem.

This stately pile is where Edward’s father, Henry VIII, stayed while courting Anne Boleyn at nearby Hever Castle. In later days, Penshurst Place was the home of Percy Bysse and Mary Shelly. It is presently owned by the  Viscounts  e L’isle, descendants of the Sidneys through the female line.


Edward VI’s Friend

Edward VI, the Boy King, a year before his accession.

In 1550, at the age of 21, Henry Sidney was knighted by Edward. In 1553, he married Lady Mary Dudley, a childhood friend of the Princess Elizabeth and daughter of the most influential man in the kingdom at that time: John Dudley, the staunchly Protestant 51 year old Lord Protector of England, Lord President of the Royal Council and, since 1551, Duke of Northumberland.

As a close personal friend of the king, Sidney must have been well aware of the strange intrigues taking place in the Royal Palace in advance of Edward’s inevitable death. The heir apparent was the Catholic Princess Mary, eldest daughter of Henry VIII by his first wife, Catherine of Aragon.

For a staunch protestant like Northumberland, the concept of a Catholic Queen was simply not feasible. The Lord Protector began hatching a plot that would keep himself in control of the realm and assure the continuation of the Protestant reformation. In March 1553 the Duke’s youngest son, 17 year old Lord Guildford Dudley, was wedded to the Protestant Lady Jane Grey, an intelligent 15 year old girl with a reasonable claim to the throne through her mother, a sister of King Henry VIII.

The Lord Protector set about persuading the dying king to change his name so that Lady Jane and not Princess Mary would succeed to the throne. At length, Edward submitted to the Duke’s desires and Jane became heir apparent.

Sir Henry must have been aware and appalled in equal parts by the antics of his father-in-law for not only was he witness to this new will but it was into his arms that the 15 year old King died at Greenwich Palace on Thursday 16 July 1553.


Lady Jane Grey


With Edward now dead, the ball was in motion for Northumberland’s plot to place Lady Jane on the throne. Sir Henry declined to involve himself in this conspiracy, preferring to mourn the death of his king instead. However, his wife, Lady Mary threw herself in at the deep end by bringing the news of the king’s death to lady Jane and then escorting her to Syon House where she was proclaimed Queen. Although he did offer shelter to the Dudleys at Penshurst after the collapse of their coup nine days later, Sir Henry and Lady Mary survived the fate that befell the Lord Protector and the innocent pretender.

The Duke of Northumberland made a last ditch attempt to save his life by renouncing his Protestantism (memorably saying “a living dog is better than a dead lion“) but failed to impress and was beheaded as a traitor on 23rd August 1553. Lady Jane Grey and Lord Guildford were similarly eliminated on 12th Feb 1554 and Jane’s father, Henry Grey went to the block 2 weeks later.

An unhappy witness to all this was the elderly Sir William Sidney who died in his 72nd year on 7 February 1554. He is buried in the church in Penshurst village. Sir Henry thus inherited Penshurst Place and that is where his eldest son, the poet and courtier Sir Philip Sidney was born on 29 November 1554. But if Sir Henry needed any confirmation that he still had the trust of the new Queen Mary and her catholic consort, Phillip II, King of Spain, perhaps he found it when Phillip agreed to stand as godfather to young Phillip (for whom he was named).


It’s a Family Affair


Queen Mary Tudor, daughter of Henry VIII, from a portrait I saw at Hever Castle.

Henry was the only brother to five sisters, all of whom married well. His eldest sister, Lady Frances Sidney, is celebrated as the founder of Sidney Sussex College in Cambridge. In April 1555 she married the 30 year old Thomas Radcliffe, 3rd Earl of Sussex, who was despatched by Queen Mary to Ireland as Lord Deputy a few months after the Hampton Court wedding. (Sidney accompanied him as Vice-Treasurer).

Lord Sussex seems to have earned the respect of Queen Elizabeth and served as Lord Deputy of Ireland from 1560 to 1566, but I think I am right in saying the Irish situation ultimately caused him to have a nervous breakdown. He died on 9th June 1583, aged 58.

Sussex nonetheless kept Ireland within the family as later Elizabethan deputies included his brother-in-laws Sir William Fitzwilliam and Sir Henry Sidney. Lady Frances died on 9th March 1589 and was interred at Westminster Abbey, having left some £5000 in her will to the foundation of a college in Cambridge in memory of her husband. The pedestrianised streets beside the college are called Sidney Street and Sussex Street to this day.

Of Henry’s other sisters, Lady Mary Sidney, married Sir William Dormer, Lady Lucy Sidney married Sir James Harrington (forefather of the Dennys of Tralee) and Lady Anne Sidney wed Sir William Fitzwilliam, later Lord Deputy of Ireland.


Sidney in Ireland


Portrait of the young Queen Elizabeth, circa 1558, from a portrait I saw at Hever Castle.

When the Earl of Sussex was despatched to Ireland as Lord Deputy in 1556, he set off with his young brother-in-law Henry Sidney as his Vice Treasurer. Three years later, in January 1559, Queen Elizabeth ascended the throne. Robert Dudley, Henry’s brother-in-law, was promptly installed on the Privy Council and swiftly became a Royal favourite. He’s the Joseph Fiennes character in Shakespeare in Love. In July of that year, shortly after the end of Franco-Scottish hostilities, Dudley’s wife, Amy Robsart was found dead with a broken neck at the bottom of a staircase in her home, prompting 500 years of speculation that Bob shoved her down because he fancied the new Queen.

At any rate, by 1560, Sussex and Sidney had been joined by their mutual brother-in-law Sir William Fitzwilliam who would continue to serve variously as Lord Deputy and Lord Justice of Ireland until 1594. One of Sidney’s first coups was to lure the young Hugh O’Neill back to England shortly after Elizabeth’s accession. Nonetheless, England’s influence in Ireland was at a low ebb. Only a year before Elizabeth’s accession, the first in a long series of rebellions against English rule had broken out in Ulster. Although unsuccessful, this rebellion confirmed the need for more stringent measures to stabilise English domination once and for all.

English jurisdiction was established in Connaught and Munster despite a number of rebellions by the local ruling families. The forests of Ireland were proving invaluable as a source of wood for shipbuilding; oak was turned into charcoal for smelting ores. Strategically, too, Ireland was ever important as a possible back door for an invasion from England’s enemies in mainland Europe. The French and Scots were in cahoots over a plot to usurp the throne and put Queen Mary of France and Scotland (ie Mary, Queen of Scots) on the throne.


Elizabethan Solution


Elizabeth’s answer was, firstly, to impose the Anglican faith upon the hostile Catholic population. She then began expanding the previously unsuccessful plantation system. One of her first moves was to appoint Sidney Lord President of Wales, in which position he remained until his death in 1586. He also stood as Cup-bearer to the Queen and, in 1564, he was created a Knight of the Garter. Among those who Sidney himself would later knight were Patrick Sarsfield’s forbear (for assisting against Shane O’Neill) and the explorer Humphrey Gilbert.


Lord Deputy Sidney


Sir Henry Sidney, Lord Deputy of Ireland.

The Earl of Sussex resigned his post as Lord Deputy in 1565, the same year Hawkins first introduced tobacco to England, and was succeeded by Sir Henry Sidney. In Modern Ireland 1600-1972 (1988) Roy Foster described the 36 year old Sidney as “by far the ablest of Elizabeth’s able band of Irish governors“. Between 1565 and 1571 Lord Deputy Sidney instigated the first deliberate policy of colonisation on Ireland, following the time honoured policy of divide and conquer. Within a few months of his appointment as Lord Deputy he had established the boundaries of modern day Counties Roscommon and Clare.

He also instigated the Seneschal or shiring of the ancient kingdom of Annaly in Longford, home turf of the O’Farrell chieftains. In the face of perpetual rebellion and constant threat of war from Scotland (at least until Mary of Scots was arrested in 1568), Sidney began to impose English laws and customs on the native chiefs but, angered by the Queen’s failure to supply the required military back up, he resigned in 1571. Perhaps she was too busy dreading her proposed marriage to Henry Duke of Anjou, which Philip Sidney so strongly opposed.

Meanwhile, a Geraldine rebellion erupted in the south west and sparked off a savage war in Munster, during which the province was laid waste. It ended with further destruction of the FitzGerald dynasty and the confiscation of what remained of their vast estates.

Sidney’s popularity at Hampton Court must have been considerably enhanced by the successes of his brother-in-law, Robert Dudley, 4th son of the late Lord Protector Northumberland, lately elevated to the peerage as 1st Earl of Leicester. Dudley had firmly ensconced himself as the Virgin Queen’s favourite. I think it highly relevant that Sir Henry Sidney’s circle included such reprobates as Sir Humphrey Gilbert (the explorer), the Earl of Leicester and the Earl of Essex. He was also evidently well thought of by the Queen herself who must have been about his age. In 1573, she enjoyed his hospitality during a stay at his property in Otford, Kent. He had retired from Irish politics and, one presumes, hoped to enjoy the rewards of loyalty.


Strike Two


Queen Elizabeth, from a portrait I saw at Hever Castle.

However, sometimes you are too good and Sir Henry duly returned to Ireland to take up a second term as Lord Deputy from 1575 to 1578. Perhaps his patience had worn thin because his actions seem to have been considerably harsher on this occasion. Or perhaps, in a time when aristos heads were falling off quicker than a prom girl’s knickers, he reckoned he ought to simply act now and mourn later. At any rate, one of the better things Sir Henry did was to write everything down and so if you’re truly fascinated by all this go have a hunt on the internet and you’re sure to find a heap of references to his works.

Sir Henry was well aware of the old Norman philosophy that enemies could be intimidated by sheer magnificence. Within a few months of taking office a second time, he ordered the authorities in Dublin to rebuild Dublin Castle with a view to making it the headquarters of English rule throughout Ireland. The castle was not completed until 1578. It was, incidentally, Sidney’s brother-in-law, Sir William Fitzwilliam (1526-1599), who first reviewed the proposals to establish Trinity College Dublin in 1590.

One of his first moves was to force the rebel leader Rory Og O’More of Leix to submit to English authority at Kilkenny cathedral in 1575. In March 1576 Sidney went to Galway to receive the submission of the chiefs of Connaught and there chanced upon Grace O’Malley (Granuaile) the Pirate Queen of Connaught, whom he described as a ‘most famous feminine sea captain‘ and ‘a notorious woman in all the coasts of Ireland‘. Mercenary as ever, she offered Sidney her ships and men in return for cash payment should he require assistance in his colonisation policy. It is said that Sidney’s poetry toting son, Sir Phillip, was quite taken with the spirited Pirate Queen.


The Essex Plantation


In May 1576 he encouraged Walter Devereux, Earl of Essex – the man who suppressed the revolt of the Northern Earls in 1571 – to take up the post of “Earl Marshall of Ireland”, cross into Ulster and purchase vast tracts of land with a view to plantation. The Essex project ended up in disaster; the Earl bankrupted himself in the process and committed suicide that September.




Derrick’s depiction of Sir Henry Sidney leaving Dublin Castle. One of the heads spiked on the wall is said to have been Rory Óg O’More’s wife Margaret.

Sidney generally liked to regard himself as an educated Renaissance man but he let himself down substantially in this regard when, on New Years day 1577, he orchestrated the brutal massacre of the Midlands chieftains at Mullaghmast. With Sky News focused on Drake’s voyage through the Straits of Magellan, as well as Philip Sidney’s friend, Prince Casimir being subsidised by the Queen to help the Dutch against the Spanish, Sidney took the opportunity to have O’More executed in 1578. His taxation programme was particularly severe and earned him the antipathy of the English authorities in Dublin.


Leicester’s Fall


In September 1578, the Dudley faction fell from power when Robert Dudley secretly wed Lettice Knollys, widow of the late Earl of Essex and daughter of Sir Francis Knoylls, one of Elizabeth’s more Puritan cousins and Privy Council. The bald, wooden-toothed Queen was furious that such a marriage take place without her knowing. Dudley’s clan were up the swanny. Sir Henry was recalled from Ireland.

He subsequently served briefly as President of the Council of Wales and the Marches and then retired to his estate at Penshurst. The 1580s was a Golden Age for England with such perks as Francis Drake circumnavigating the world, the conquest of Virginia and running water being pumped into people’s homes for the first time. During this time Sidney oversaw the plantation of the Italian garden at Penshurst. He died at Ludlow in Shropshire on 5 May 1586 in his 56th year. His wife, Lady Mary, followed him that same summer.


Ireland after Sidney


In 1588, the success of Elizabeth’s policies was borne out when the survivors of the Spanish Armada were washed up on the west coast of Ireland and were mostly massacred by the local Irish sheriffs and their forces. The thorn in Elizabeth’s side was Ulster, the last outpost of the Irish Chiefs. Hugh O’Neill, Earl of Tyrone, was the prime mover in the last serious assault on English power in Ireland. As a boy, Hugh O’Neill had been taken into the care of Elizabeth’s viceroy, Sir Henry Sidney, and raised as an English nobleman. After returning to his native County Tyrone, he had shown his loyalty by helping to suppress the Desmond rebellion in Munster. In 1587 he was recognised as Earl of Tyrone, and was granted extensive territory under the English Crown.

A year later, however, he ignored a government order to execute survivors of the Spanish armada who landed in Ireland, and in Dublin there were increasing doubts about O’Neill’s loyalty. The doubts were justified. O’Neill was allowed to keep 600 men in arms at the Queen’s expense, and by regularly changing them he was able to train a substantial army. A story is told of O’Neill ordering lead from England to roof his new castle at Dungannon; in reality it was for making bullets.


Death of Sir Philip Sidney


Sir Philip Sidney (1554-1586), poet, courtier, scholar, soldier.

It is perhaps fortunate that Sir Henry and Lady Sidney passed away in the summer of 1586 for that autumn their eldest son – Sir Philip Sidney – was fatally wounded at the battle of Zutphen in the Netherlands. Phillip had been a protégé of Queen Elizabeth’s favourite, Robert Dudley, Earl of Leicester, a brother of Philip’s mother. Young Philip studied at Shrewsbury School, where he befriended Fulke Greville, and Christ Church in Oxford alongside Sir Walter Raleigh, from 1568 to 1571.

From 1572 to 1575, Phillip was on a Grand Tour of Europe with Elizabeth’s spymaster and future father-in-law, Sir Frederick Walsingham. During this time the two men witnessed the savage massacre of French Protestants on St. Bartholomew’s Day (24 August 1572) which followed the marriage of Henry of Navarre to Margaret de Valois. There’s a wonderfully saucy French film about it all somewhere called La Reine Margot.

In 1576, Philip succeeded his father as Cup-bearer to the Queen, a purely ceremonial duty, in which year he had joined his father and the Earl of Essex on a military foray into Ireland. Around about this time, Philip turned his mind to poetry. In 1577, his sister Mary – also a poet – married Henry Herbert, 2nd Earl of Pembroke. It was for her that Phillip Sidney wrote his poem, Arcadia.

His younger sister, the Countess of Huntingdon, was guardian to Penelope Devereux, the stunning daughter of the Earl of Essex. She brought Penelope to Penshurst one day and so deep was Phillip’s infatuation that he penned the great sonnets of Astrophil & Stella to her but his passions never came to anything.

He was knighted in 1685 and married Frances Walsingham, daughter of the mischievous Secretary of State with whom he had travelled a decade earlier. She would later marry Robert Devereux, 2nd Earl of Essex, Penelope’s brother, who led an invasion of Ulster in 1598 but was executed for treason in 1601. Frances then married Richard Burke, Earl of Clanricarde, with whom she settled in Ireland.

Alas for Sir Philip, this enormously popular Elizabethan poet had his thigh bone shattered by musket shot while serving with his uncle Robert against his Godfather Phillip of Spain’s Catholic forces His death occasioned a month of mourning in the capital. He occasioned a state funeral in Saint Paul’s Cathedral becoming the first ever commoner to merit such a tribute and the only commoner to do so except Admiral Nelson and Winston Churchill.