Disorderly Conduct: the Knights of St John under Henry VIII

Museum of the Order of St John Justin Bailey, Museum Office Assistant

In 2019 the Museum is exploring the Order of St John’s unique connections to royalty throughout its 900-year history. 

As one of England’s most infamous, charismatic and radical royal figures, King Henry VIII has left a lasting legacy on the nation in many forms. Presiding over the Dissolution of the Monasteries from the 1530s onwards, he oversaw the extinction of the Order of St John in England, and is now remembered as an infamous figure in its history. But the complete story of his links to the Order is surprisingly complex and reveals that he inherited a close and productive relationship with its senior figures, with the Order often at the centre of political intrigues which spanned across all Europe, before its eventual demise as Henry’s relationship with the Catholic church broke down.  

The Order of St John first became established in England in around 1128, relying on royal and feudal patronage to establish landholdings which could be used to generate revenue and attract recruits to the Order’s causes in the Holy Land.  As its status grew, the Order became England’s largest ecclesiastical landholder by 1340, owning many properties donated directly by the Crown. However, the Order’s status in England was subject to difficulties arising from its dual loyalties, both to the English king, and to the Pope as head of the Roman Catholic church and ultimate arbiter of the Order’s activities and responsibilities. Support from the English Crown often came with restrictions; from 1279 all religious organisations needed to apply for a Royal licence in order to acquire more property and had to seek permission from the Crown to hold fairs and markets to generate income. Tensions would often arise between the Crown and the church over the appointment of a new Prior (head of the Order in England), and the Crown kept a close eye on the amount of money that the Order sent abroad to fund their crusading activities.  

Despite these points of conflict, the relationship between Crown and Order became remarkably close under Henry VII, the first Tudor King. Thomas Docwra, the Prior of England, was one of Henry’s trusted advisors, and was often deployed as a Royal ambassador. Docwra, a worldly figure who had travelled widely and gained extensive military experience in his time with the Order, was ideally qualified to carry out diplomatic work for the King, including negotiating marriage treaties, and commercial and financial accords. Docwra is best known now as the builder of the current St John’s Gate, as part of an extensive and lavish project which turned the Order’s home in Clerkenwell into a grand residence, which would be frequently be used to host foreign dignitaries, and even the King, who stayed as a guest in the summer of 1508. 

Painting of Thomas Docwra, Prior of England, by E.C. Dingli
Thomas Docwra LDOSJ1787 (image ©MOSJ)

In 1506, possibly on Docwra’s recommendation, Henry was granted the special title “Protector of the Order”, a unique honour which recognised his financial and military support for the Order’s activities against the Ottoman Turks in the Mediterranean, and may well have been bestowed to flatter him into sending further aid. When the young Henry VIII replaced his father as king, he inherited this relationship, and was eventually granted his own protectorship by the Order. Docwra’s use to the Crown only increased, and he continued to act as a de facto minister and civil servant in anticipation continued support from the King for the Order’s activities. Docwra was sent abroad for diplomatic business multiple times between 1510-1514, and every year from 1517 to 1521, and accompanied Henry to meet his French counterpart, King Francis I, during the festivities of the Field of the Cloth of Gold in 1520.  

From the outset of his reign, Henry was interested in increasing England’s status as an important power in Europe. In this, he differed sharply from his father, who had little interest in foreign conflicts and had focused primarily on maintaining peace as a foundation for economic prosperity. While the older Henry had been notoriously frugal with the Crown’s finances, the younger Henry spent lavishly on the military and on his court, both of which served as status symbols and signifiers of power at home and abroad. This showy behaviour put pressure on the Crown’s finances, and Henry frequently sought grants and subsidies from Parliament to support his spending. 

Meanwhile, Docwra’s continuing usefulness to the King ensured the Order would be allowed to hold on to its property and its revenue generating activities in England without undue interference, while maintaining access to a direct line of Royal financial support. This close relationship was not without difficulties, and Henry appears to have extracted maximum return in exchange for his generosity. He frequently refused to allow Docwra to attend to Order business abroad in order to keep him available to carry out work for the Crown and recalled English knights from the Mediterranean as soon as they had completed their military training so they could serve his needs first.  

Meanwhile, the Order was still involved in intense conflict in the Mediterranean, and in 1523, after a six-month siege and fierce fighting against Ottoman forces commanded by Suleiman the Magnificent, the Knights of St John were forced to leave their Rhodes stronghold, leaving them homeless. The lack of a permanent base and the cost of operating a large contingent of ships without its own port facilities put strain on the Order’s finances, while its chastening defeat at Rhodes called into question its fitness to pursue its aims of defending Christendom and stopping the encroachment of Ottoman forces into Europe.  

While the knights negotiated with Charles V of Spain for ownership of the island of Malta as their new home, Henry, feeling left out from discussions, and unhappy at funding an Order whiccould not serve a useful purpose while homeless, considered seizing the Order’s cash and property in England to supplement his own. In 1527, just at a time when diplomacy and tact were needed to manage this difficult situation with the King, Prior Docwra, now in his late-60s, fell seriously ill. Henry immediately made plans to sequester Docwra’s property and possessions, including the Clerkenwell Priory, in the event of his death.  

When Docwra died, the Order assigned William Weston as their new Prior of England. Weston, a veteran of the siege of Rhodes, had excellent pedigree in Order circles, and several of his uncles had already held high-ranking roles in the Order before his nomination. Despite this, Henry initially refused to accept his appointment and prevented him from accessing Priory lands while he considered his relationship with the Order. Weston eventually regained control of the Priory after agreeing to pay a levy of £4000 a year to the Crown. After a personal visit from Grand Master de l’Isle Adam Henry acquiesced, dropped his financial claims, and accepted Weston’s appointment. He even fulfilled a long-awaited promise of extra support by gifting the Order 19 bronze cannon and 1023 cannonballs for its arsenal. One cannon is on display at the Museum today, and it still bears the insignia of both Henry and de l’Isle Adam. This sudden act of generosity was an opportunity for Henry to impress his fellow leaders abroad, but it also demonstrates his temperamental character. Soon Henry’s political and religious affiliations would shift again, undergoing a radical transformation which would trigger the collapse of the Order’s status in England.        

Image of bronze cannon featuring Henry VIII's coat of arms
LDOSJ 2625 (image ©MOSJ)

The Order had managed to secure Malta as its new home by 1530, but by this time, Henry was in deep dispute with Pope Clement VII over the annulment of his first marriage to Catherine of Aragon. This quarrel steadily grew to dangerous proportions, eventually leading Henry to seek a split with the Catholic church in one of the most revolutionary acts in English history. 1534’s Act of Supremacy enshrined his status in law as the head of England’s church, and soon after he began to seize Catholic assets, and the Church of England was formally created. Increasingly restrictive anti-Catholic regulations were introduced throughout the 1530s, making the Order’s presence in England all but untenable, although its historically close connections to the Crown may have offered some protection, since it was one of the last religious houses in England to be formally dissolved. 

 At least five knights of the Order are known to have resisted the dissolution by refusing to denounce the Pope’s authority when asked to do so. This was now considered high treason in England, and it resulted in a swift and brutal response. Two of the knights, including Adrian Fortescue—a cousin of Anne Boleyn and a former attendant of the King—were beheaded at the Tower of London in July 1539. Shortly afterwards, a third and less senior knight, David Gunstone, was dragged around Southwark on a wooden frame before being gruesomely hung, drawn and quartered. 

However, not all knights put up resistance. Religious houses in England came under significant pressure to undergo peaceful self-dissolution, and individuals who agreed to this were rewarded with generous pensions if their status was high enough. While some English knights re-joined with their Order brethren in Malta, others remained in England, continuing to live on portions of their original estates and working in service of the Crown. William Weston, the last Prior of England, was set to receive the most generous pension of all at £1000 a year, but is alleged to have died on 7th May 1540, the same day the act formally dissolving the order of St John in England was passed by Parliament, leading to suggestions that he had died of sheer grief. 

In 1540 Henry signed a warrant for the destruction Clerkenwell Priory, instructing that the buildings be sold or dismantled and stripped for useful construction materials like timber, lead, iron and glass. Some of this material was eventually used to build the original Somerset House, a grand mansion on the north bank of the Thames, but ultimately much of the core structure of the Priory was left intact, a near unique outcome for a major religious site in Reformation England. Much of the already grand site was re-purposed into elite urban residences, and some of these survived until the 18th Century without significant redevelopment. 

It seems clear that the Order’s privileged status resulted in some special treatment during a time of extraordinary upheaval in English society. The problem of divided loyalty which had underscored the Order’s relationship with the Crown for hundreds of years had traditionally been dealt with pragmatically for mutual benefit, but Henry’s dispute with the Catholic church made it impossible to ignore, and the Order’s demise, like that of other religious houses in England, soon became inevitable.  

Find out what happened when the Order was briefly re-established under Henry VIII’s daughter, the Catholic monarch Mary I in this blog post



Excavations at the Priory of the Order of the Hospital of St John of Jerusalem, Clerkenwell, London, Sloane, Barney and Gordon Malcom, MOLA, 2004 

Henry VIII, Guy, John, Penguin, 2018 

The Knights of St John in the British Realm, King, Edwin (revised by Harry Luke) Order of St John, 1967 

The Knights Hospitaller of the English LangueO’Malley, Gregory, OUP, 2005 


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