Tom Skeleton was a servant to the Pennington family. However he was not an obscure character in the household, but a jester, hired to inspire mirth. But Tom was a devil disguised in the costume of a clown. Fools and jesters were often part of a royal court or noble family and by virtue of their position could often speak harsh truths to their ‘betters’ in the guise of drollery.
Muncaster Castle was built on the ruins of a Roman encampment located on the northwest coast of England. The ruins of an old Roman baths was found just a few miles away in nearby Ravenglass The Pennington family has called it home for around 800 years.
Little is known about Tom Skelton, which is not surprising since in truth he was a servant, but none can doubt he had some sway, as most servants did not have a portrait done of themselves. He is pictured holding his last will and testament.
He was hired by Sir Alan Pennington as a teacher and steward for his nephew, William Pennington who was 14 years old when his father died and he became the Lord of Muncaster Castle.
Skelton was no doubt a psychopath who only thrived if he had a constant dose of extinguishing human life, however he was intelligent enough to realize he could not go willy-nilly killing people. So he fed his dark passenger by sitting underneath a chestnut tree, which still stands today on the castle grounds. It was by a road that was frequented by travelers, and he would offer directions. If he didn't like the person, which was probably a very high percentage, he would direct the traveler to use a road which took you to a patch of quicksand which offered little chance of escape.
An unknown source told of Tom Skelton recovering the bodies, decapitating them and then burying the heads under different trees in the area. Were these his trophies?
In 1825, John Briggs, a local journalist published an essay that described a story about the Jester of Muncastle Castle. Sir Alan Pennington had a daughter name Helwise. She attended a May Day fair in the village dressed as a shepherdess. Released from the strictures of her class due to her costume, she danced with a carpenter named Richard. Wild Will of Whitbeck took a fancy to the mysterious shepherdess who rejected him. Little did he know that the shepherdess and the carpenter were already involved in a secret romance. He followed the couple that evening and saw when she went to Muncastle Castle, leaving no doubt to her true identity.
Like many vain and narcissistic suitors throughout history, if he could not have the object of his desire, then she would be not be with the one he had been rejected for. He knew the Sir Ferdinand Hoddleston of Millum Castle wanted to marry Helwise. Having attended Sir Ferdinand when he went on sporting excursions he was able to gain an audience with him. He tells the tale of Helwise and her secret suitor. Sir Ferdinanrd is outraged that the beautiful Helwise prefers a lowly carpenter to him, and sets out the next day to visit Sir Alan. Upon arriving at the castle, he is met by Tom Skelton who asks him why he is visiting Muncaster Castle. He says he has a grudge against Dick Carpenter, and Tom the Jester says he has one too. Sir Ferdinand promises him three crowns and protection from reprisal if he kills the man with his own axe.
Not needing much inducement to kill and be rewarded for it, Tom Skelton waited until the carpenter was taking a nap. He snuck up on him in a shed and with one blow from his axe, beheaded him. He hid the head under some wood shavings, and he was so confident of escaping punishment that he returned to the servant's hall and told them of what he had done.
The plan backfired on Sir Ferdinand, because Helwise could only think of her dead lover and rejected him and all suitors. She ultimately went into the Benedictine Convent of Maiden Castle for the rest of her days.
Sir Ferdinand's conscience gave him no peace so he joined the army and was killed at the Battle of Bosworth Field. He left an estate to St. Mary's Abbey of Furness, with the request of prayers for his soul and that of the young carpenter..
It is unknown how many deaths Tom Skelton engineered or had a direct hand in.
Sir Alan died and the young lord of Muncaster went to live with his relatives the Bradshaigh at Haigh Hall in Wigan. Elizabeth Bradshaigh was William's aunt. Sometime between 1659 to 1665 Tom's first portrait was finished. The burial of a Thomas Scelton of Haigh is recorded in the Wigan parish register on January 13, 1668 (1667 Old Style), which fits with the late-middle-aged look of the portrait.
When William Pennington reached his majority of age and was returning to Muncaster, another portrait of Tom the Fool was painted to be left behind with the Bradshaw family. There is no record of Tom Skelton after 1659 so there is a possibility he died while the family was at Haigh Hall.
Tom Skelton was the last jester of Muncaster Castle and Haigh Hall. The puritans probably frowned on them, and they had fallen out of fashion with the restoration of Charles II.
Unsurprisingly his portrait is the center of ghostly phenomena. Heavy steps and what sounds like a body being dragged up the stairs has been heard by different people. There is also the haunted Tapestry room was previously used as a children's nursery. Visitors spending the night there, hear children crying. Some believe it is the ghost of Margaret Pennington who was a young child when she died of screaming fits in the 19th century. There are also reports of a woman singing.
Another Muncaster Castle ghost is a White lady who is thought to be Mary Bragg who was a housekeeper or local girl who was murdered in 1805. There are different versions as to why she was killed but it's believed a rival for the affection of a footman inspired a plan to permanently remove Mary out of the picture. She was duped into leaving with two men who said her lover was ill. They took her to a lonely spot, killed her and dumped her body into the Esk River. Eventually her badly decomposed body was found. It's said she haunts the grounds and roads around Muncaster.
His will, which predicted Skelton’s own death in the very same quicksands to which he is rumored to have sent many travelers to die, hangs from a table to his right (the viewer’s left) on the portrait. The will reads as follows:
Thoms. Skelton late fool of Muncaster last will and Testament
Stranger Than Fiction Stories by M.P. Pellicer