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King Henry VIII: Accomplished Leader and Number 1 Gambler of England

King Henry VIII is remembered for many things including initiating England’s reformation and separation from the Roman Catholic Church in addition to having six wives over the course of his lifetime.

One commonly unknown fact about him, that’s vital to understanding his true character, was his addiction to gambling.

King Henry VIII spent many hours playing anything from Dice to Bragg, competing against both monarchy leaders and commoners. He was considered one of the most unlucky gamblers of his time, losing a myriad of money and prized possessions almost every time he gambled.

Growing up in the Palace

King Henry VIII, the son of King Henry VII and Queen Elizabeth from York, was born at Greenwich Palace on June 28th, 1491.

He would have had six siblings but only three of them survived infancy: an older brother: Arthur, Prince of Wales and two sisters: Mary and Margaret. Since young Henry was the second born son, he wasn’t next in line to obtain the throne.

Before he could even form proper sentences, little Henry was granted with prestigious titles that were essentially meaningless, as he was in no position to take on any real responsibilities. When he was only two years old, he was appointed Constable of Dover Castle and Lord Warden of the Cinque Ports.

Less than a year later, he took on the positions of Earl Marshal of England and Lord Lieutenant of Ireland. Young Henry accomplished more in his toddlers years than most people do in a lifetime.

There are even more titles that Henry received before turning five,

as we only mentioned the most important ones.

As one might imagine, the majority of young Henry’s childhood consisted of getting the best possible education available in England at that time. Historians also recorded that Henry spent a great deal of time with his father, as they had a very close relationship.

This was rare, as most Kings during that time period didn’t spend much time with their family members.

In 1502, Henry’s brother became the new Prince of Wales after marrying Catherine, the Princess of Wales. Shortly after their extravagant wedding day, Arthur passed away due to unknown causes, making Henry the next in line for the thrown.

In order to prepare for his upcoming role, Henry was given more responsibilities and more prestigious positions. Among these positions, Henry was responsible for marrying his brother’s widow and taking on the position of the new Prince of Wales.

Unfortunately, there were some arguments concerning their marriage and for a while, it looked as if it was going to fall through.

Becoming King

King Henry VII passed away on April 21st, 1509 just before Henry’s eighteenth birthday. Although he was inexperienced in some ways, Henry was happy to accept his new title as King Henry VIII and all of the responsibilities that followed.

Before his coronation, he married Catherine; they had a very modest wedding and didn’t invite many guests.

Upon his coronation, King Henry VIII made a bold decision to fire two of his father’s ministers, Sir Richard Empson and Edmund Dudley, who were accused of treason and believed to be partially responsible for his father’s death.

Under King Henry VIII demands, they were publically executed the following year.

Another courageous decision that Henry made early on was to get involved with the war going on between France and Venice. He initially formed an alliance with France but then he agreed to help Ferdinand, the Leader of Venice at the time, and signed a pact to show his commitment.

In 1513, Henry and his army successfully invaded France which resulted in the battle known as “Battle of the Spurs,” as many soldiers lost their lives.

Queen Catherine: King Henry VIII’s First Wife

It was around this time that Henry and Catherine announced that there were expecting a new addition to their family; the whole kingdom prepared for the arrival of this new baby.

Regrettably, the baby girl died upon birth several months later, causing a great amount of grief for the newly married couple. The good news is that they were able to have a healthy baby boy, named Henry, just a year later.

The whole kingdom celebrated the birth of their new son but when he was just a few weeks old, he grew terribly ill and passed away. Catherine continued to have stillbirths until she finally had a healthy daughter named Mary, who lived a long and fruitful life.

King Henry was desperate for a son at this point and so he started obtaining mistresses from other countries to fulfill his desires.

One of his mistresses, Elizabeth Blount, gave birth to their son, Henry Fitzroy, in June of 1519. When the boy was of age, he was anointed Duke of Richmond, in hopes that he could one day carry on his father’s position as King.

He, unfortunately, died childless fourteen years later, leaving no heir to the throne. Now King Henry VIII was more determined than ever to have a healthy, fertile son. He made the drastic decision to divorce Catherine, which was a much more complicated process than it is in today’s society.

Initiating the English Reformation

The Roman Catholic Church was strictly against divorce, as they believed that marriage was a lasting contract that could only be repealed through death.

As only widows were free to re-marry, King Henry VIII wouldn’t only be prohibited from getting remarried, but he would be excommunicated from the Church if he went against their wishes.

Initially, King Henry VIII purposed that under “Papal Dispensation,” he could be exempt from certain laws of the church, including their laws concerning divorce, due to his position as King.

The Pope denied his request, which lead King Henry VIII to come up with a new plan. He ordered the Archbishop of Canterbury to grant him a divorce, although this meant that they both had to directly go against what the Pope had commanded.

Eventually, due to King Henry VIII’s actions, England started to break away from the rule of the Roman Catholic Church and in the 1534 Act of Parliament; King Henry VIII became the Supreme Head of the Church.

This would forever limit the Pope’s power and give more power to the Kings that preceded him.

The Dissolution of the Monasteries

After being appointed Supreme Head of the Church, King Henry said this to his people,

“Well-beloved subjects, we thought that the clergy of our realm had been our subjects wholly, but now we have well perceived that they be but half our subjects; yea, and scarce our subjects; for all the prelates at their consecration make an oath to the Pope clean contrary to the oath that they make to us, so that they seem to be his subjects, and not ours”.

One threat to King Henry VIII’s new power was the monasteries where the monks lived, as these monks were the wealthiest men in all of England and they owned the most property.

King Henry VIII sent several government officials to the monasteries to spy on the monks and to see if they were doing anything wrong that he could use as an excuse to execute them. It was discovered that the Monks and Nuns were starting families, against the Church’s commands. They were also using the people’s money for corrupt practices.

This news disturbed the people of England and caused them to support the King’s actions that were later referred to as “The Dissolution of the Monasteries.” Monks and Nuns were executed for their crimes, causing King Henry VIII to acquire the majority of their wealth and land.

He used a great deal of that money to build up England’s military, which greatly pleased his people. He also starting building several advanced defense systems along the southern and eastern coasts of England to stop Spain from a possible invasion. These systems became known as “King Henry VIII’s Device Forts.”

Queen Anne: King Henry VIII’s Second Wife

King Henry VII’s is known for writing long love letters to his wives. The following is an exurb from one of his initial love letters to Anne Boleyn during their courtship; it will be clear that he had to convince her that he was worthy of her love.

“I beseech you now with all my heart definitely to let me know your whole mind as to the love between us; for necessity compels me to plague you for a reply, having been for more than a year now struck by the dart of love, and being uncertain either of failure or of finding a place in your heart and affection…”

King Henry VIII and Anne Boleyn had a private wedding towards the end of 1532. It wasn’t too long after the ceremony that Anne was pregnant and soon bore a young daughter which the couple named Elizabeth in honor of the King’s mother.

The beginning of their marriage was full of love and passion but their personalities soon conflicted with one another. Queen Anne was bold and domineering; she didn’t want to take on the duties of a submissive wife. Her personality, on top of her inability to bear a son, caused King Henry VIII to look into getting another divorce.

It was around this time that the King was in a horrible jousting accident where he was thrown off of his horse and was critical condition. Queen Anne was about fifteen weeks pregnant and the news of her husband caused her to go into shock and have a miscarriage of what would have been their firstborn son.

Queen Anne seemed to have lost her mind after the loss of their son, supposedly sleeping around with members of her family, including her brother. She was soon arrested for incest and treasonable adultery, with her punishment being public execution.

It was around this time that King Henry VIII started gambling against other monarchies in nearby countries, as he was hoping it would distract him from the pain of not having a son and the betrayal of his former wife.

Several Other Marriages

Since Jane Seymour was Queen Anne’s lady in waiting, she and Henry were immediately engaged after Anne’s execution, getting married just ten days after.

On October 12th, 1537, King Henry VIII finally got the heir to his thrown when Jane gave birth to their son: Prince Edward. It was a very difficult birthing process for Jane and she died less than two weeks later due to a persisting infection. Henry spent some time to mourn the loss of his wife before pursuing another woman to take her place.

The women he ending up choosing was Anne, the sister of the Duke of Cleves, as Cleves would be an important ally as England steered away from the Roman Catholic authority.

Before the two were officially married, King Henry VIII found a more attractive woman that he was hoping could be his wife instead. Anne of Cleves agreed to instead take on the title of “The King’s Sister,” which came with a generous allowance and two extravagant houses.

After that King Henry VIII soon married a beautiful woman named Catherine Howard, who was Anne-Boleyn’s cousin. She allegedly had an affair, causing both her and her lover to be beheaded. King Henry VII’s sixth and final wife was Catherine Parr, a wealthy widow who greatly respected her husband and was just what King Henry VIII needed.

England’s Number 1 Gambler

King Henry VIII was often referred to as, “England’s Number 1 Gambler,” as gambling was his favorite activity to do during his spare time.

He enjoyed playing dice, a version of Backgammon known as “Tables,” and a checkers-related game referred to as, “Betting Queek.”


In addition to those two, a new phenomenon was sweeping through London called “Bragg,” which historians believe is one of the games that poker is derived from.

There were many gambling events that took place across Europe where citizens from all over the country would travel to gamble against each other, in hopes of winning a fortune. King Henry VIII always participated in these festivities but luck was rarely ever on his side. Over the course of two years, he lost £3,250 playing cards: a large sum of money for that time period.

King Henry VIII is infamous for losing the beloved Jesus bells of old St. Paul’s church against Sir Miles Partridge on a single roll of dice. He claimed that those bells were practically worthless, except for the metal in which they were made out of.

This offended many people across England, so King Henry VIII convicted Sir Miles Partridge of treason in order to gain his people’s respect once more. Sir Miles was publicly hanged on Tower Hill for everyone to see; very few people wanted to gamble against the King from that point on.

Nearing the End of His Life

By looking at any portraits of King Henry VIII, it’s probably easy to tell that he was overweight. Towards the end of his life, he would have been considered obese with a waist exceeding fifty-four inches.

His obesity can be traced back to his jousting accident of 1536, which caused him to be bed written for several months while his leg healed. His leg never completely healed, so his ability to do physical activity was very limited, causing him to gain an immense amount of weight very quickly.

Historians suggest that he probably developed Type 2 Diabetes over the years, which probably caused his condition to worsen.

Henry’s obesity led to his death on January 28th, 1547 at the age of 55.

The last words he spoke before he passed away were supposedly, “Monks! Monks! Monks!” The funeral service for King Henry VIII was held at St. George’s Chapel in Windsor Castle. His only son, who became known as King Edward VI, succeeded him on the throne.