While George III is most famous for his “madness,” he was in fact better-renowned in his younger days for being almost annoyingly upright and fastidious. He married responsibly, embraced a quiet family life, and was usually quite horrified when scandal touched any of his relations. Unfortunately for him that happened rather frequently, and while his children’s exploits are more famous, his siblings also gave him a run for his money. We’ve discussed before his younger sister, Queen Caroline Matilda of Denmark & Norway, as well as his brother, William, Duke of Gloucester and his marriage to Maria Walpole, but today we’re going to turn to the eldest of his younger brothers, Edward, Duke of York.

Edward was his parents’ third child, born on March 25, 1739 at Norfolk House in St James’s Square. His father, Prince Frederick of Wales, was heir to the British throne, but notoriously on the outs with his own father, George II, while his mother, Princess Augusta of Wales was very shy, very German, and very afraid of rocking the boat with her British in-laws.

Only nine months younger than his elder brother, Prince George, Edward had the benefit of a constant companion, and none of the responsibility that came with being his father’s eldest son. By the time he was 11, he had been joined by another five siblings – Elizabeth, William, Henry, Louisa, and Frederick. Edward was reportedly a bit of a ham growing up, a natural prankster, and considerably more boisterous than George. And while George was considered the handsomer of the two, it was Edward who was his father’s favorite.

The middle-class idyll that Frederick and Augusta cultivated for their growing family, however, came to a screeching halt in March 1751 when Frederick suddenly died, his wife five months pregnant with their ninth child. Caroline Matilda would be born that July.

Immediately, Augusta’s first concern was retaining custody of her children without her husband’s protection. As king, George II had the ability to insist on physical possession of his grandchildren, an arrangement that might not have seemed outlandish given that Prince George was now his heir. George II’s own father, George I, had implemented such an arrangement when the two men had a falling out, and the forced separation of George II from his three eldest daughters had solidified the Royal Family’s dysfunction for a generation. But perhaps George II had learned something from the experience, because he made it clear that he would let Augusta maintain her household, and her children within it.

At least, for a time. In June 1756 Prince George turned 18 and George II offered his grandson his own household, having grown considered about the influence James Stuart, Earl of Bute had on the Dowager Princess of Wales and the family. Prince George refused to come to court, and wouldn’t condone separation from his mother, but he did allow the establishment of a separate residence at Savile House that autumn under Bute’s control. Edward followed him, which meant that the 17-year-old had his first real taste of freedom.

Edward, unlike George, wasn’t a fan of Bute’s, and the two brothers appear to have naturally drifted apart during this time, with the younger throwing himself into making new friends and entering society. He took to wandering the streets of London, frequenting taverns, attending the theatre, and, well, women.

One stood apart from the others – Lady Mary Coke, a rigid and very proper widow, who just so happened to be a daughter of the Duke of Argyle. Her marriage to Edward Coke, heir to the earldom of Leicester, had been unhappy, and the couple separated in 1749. Her social status was thankfully (for her, at least) preserved by his timely death a year later. Now wealthy and independent, Mary was social, an accomplished musician, and an avid theatre patron. By the end of 1758, Edward was in love.

She was not, however, his first, a dubious title that either went to the Duchess of Richmond or Lady Essex, both married and both older than him. Mary, too, was 32 to his 19, and so she presented something of a challenge. Though interested in the Prince’s attention, she was also cognizant of appearances, and so she played it cool when Edward began sending her gifts, writing her letters, and calling on her house at Green Park. When she fell ill and Edward sent a note inquiring after her health, she chided him for writing too early. He responded:

“Prince Edward sends his compliments to Lady Make Coke and cannot help making another attempt to inquire how she does. Is provoked with himself for not remembering the fashionable hours better than to inquire after a lady’s health at so early an hour, as must oblige her to send back word she’s asleep out of complaisance and conformity to an idle, dissipated and unthinking age.”

And so they parlayed for the next several months, despite Edward’s consistent distractions with women who posed less of a challenge.

As for Edward’s royal career, he served in the Battle of Saint Cast in September 1758, and was promoted to captain of the HMS Phoenix the following year. In April 1760, George II elevated his grandson to the dukedom of York, and that October he died, with Prince George becoming George III at the age of just 22. All of court soon immersed itself in the succession, and then the necessity of finding the new king a suitable queen. George chose Charlotte of Mecklenburg-Strelitz, a young German princess who spoke no English and was utterly unprepared for her new role, but whose reputation was spotless.

Edward and his brother, William, escorted the new queen to her wedding in September 1761, and when she faltered, he famously whispered to her, “Courage, Princess, courage.”

As George started his family with Charlotte and took over the reins of government, Edward continued his hot-and-cold friendship with Mary and establishing himself as a man-about-town. The latter, of course, required quite a bit of money, particularly as he developed a taste for gambling. By early 1764, he was getting others to ask his brother to increase his allowance, too afraid to make the request directly. But unfortunately for him, George was both himself frugal and not very understanding of what he regarded as Edward’s dissolute lifestyle.

In Parliament’s first session in 1767, the King did recommend an increase of a few thousand pounds to Edward’s annuity, but it came nowhere near covering his expenses. It was a situation that would continue to play out through George’s reign once his sons took up his brothers’ mantle of profligate spending.

Shortly after acting in a play for some of the finer members of London society, Edward duly announced that he was going abroad (where, incidentally, the cost of living was cheaper). His plan was to travel through France, Genoa, Turin, the Swiss Alps, and then end his trek in Paris before returning to London. George, however, wasn’t having it, and quickly wrote to him:

“Brother. A report is very prevalent that you have some intentions to present at the reviews of Compiegne*. I cannot give great credit to this as you know how I insisted on your not making any stay in France…I am if possible more averse now to any of my Family going there from what I learnt from the hereditary prince [of Brunswick].”

*Essentially a celebration of the French military

Naturally, Edward ignored him and immediately set off for France. Even more, he not only attended the review at Compiegne, but rode on horseback alongside King Louis XV, who was receiving him with all due honor (if not officially since the trip was private) of his rank.

He tarried in France through the end of July and then made for Monaco where he promptly fell ill. From his sickbed, he wrote to his brother, William:

“My Dear Brother, the weak state I find myself in induces me, while it still may be in my power, to desire you to pay my last weak duties to the King, and if at any time I should have incurr’d his displeasure, I hope the generosity of his temper will at least make him forgive my unheeded past conduct which is all at present I have in my power to offer. Pray say the same to my mother. Pray give my friendship and love to my dearest sisters Augusta and Louisa and Caroline and my dear brother Harry. Adieu my dearest brother, E.”

A week later, on September 17, Edward passed away at the age of 28 at the Prince’s Palace of Monaco. His body was transferred back to England and he was subsequently buried in Westminster Abbey.

Mary Coke, however, was ill-prepared for the end of her nearly decade-long royal romance. She learned of Edward’s death in Frankfurt, and immediately returned to England where she put on quite the show of grief. She was, according to historian Stella Tillyard, upset by both friends bringing up the Duke’s death or failing too. She poured her heart out in her journals, and became convinced that Edward must have tried to send her a private message from his deathbed that got lost along the way. Finally, hearing of her sadness, one of Edward’s companions visited her house to tell her of his last days, noting that he “seemed to wish to do something more.” He was being kind, of course, but Mary took comfort that the “something more” was saying goodbye to her.

Edward’s relationship with Mary became something of a joke on her after his death, thanks in no small part to her own behavior. She became convinced that Edward had planned to propose after his return from the continent, and insinuated they had an understanding, if not an unofficial engagement, and as such she donned the mantle of royal widow to the disdain of everyone around her. It was more than a little bizarre given the longevity of their relationship, and how it had seemingly evolved from ardor on the Prince’s part to a comfortable friendship. It was a charade she continued until her own death in 1811.