George, the Duke of Clarence, was a member of the House of Plantagenet and brother to two kings of England, Edward IV and Richard III. However, despite his royal connections, George was not a popular figure in his own time, and his life ended in a particularly gruesome way - he was executed by drowning in a barrel of wine.

George's downfall began in the late 1460s, during the Wars of the Roses, a series of civil wars fought between the House of Lancaster and the House of York for control of the English throne. George initially supported his brother Edward IV, who was the Yorkist claimant to the throne, and played a key role in Edward's victory at the Battle of Towton in 1461.

However, George's loyalties began to shift in the 1470s, when he became increasingly dissatisfied with Edward's rule. He began plotting against his brother, and in 1477 he was accused of treason and arrested.

George's trial was held in the Tower of London, and he was found guilty of plotting against the king. His sentence was particularly unusual - he was to be put to death by drowning in a barrel of Malmsey wine.

According to contemporary accounts, George was taken to the Tower Green, where a large barrel was filled with wine. He was then stripped of his clothes, tied up, and forced into the barrel, which was then rolled into the Thames. The idea was that the wine would symbolize George's love of luxury and excess, and that his death by drowning would be a fitting punishment for his supposed crimes.

However, there is some debate among historians as to whether this account is entirely accurate. Some have suggested that the story of George's execution by wine was a later invention, designed to add a macabre twist to the already grisly tale of the Wars of the Roses. Others have pointed out that drowning in wine would actually be a relatively painless way to die, as the alcohol would numb the senses.

Despite the controversy surrounding the details of George's execution, there is no doubt that his death was a particularly gruesome and unusual one. Today, the story of the Duke of Clarence's execution by wine remains one of the most enduring and intriguing tales of medieval England.