Jack o' Kent

Jack o' Kent (or Jack-a-Kent) is a figure from English and Welsh folklore associated with the Welsh Marches. Depicted as either a clever cleric or a cunning wizard, he is best known for outwitting the Devil in a series of wagers and contests. His stories are especially prominent in the counties of Herefordshire and Monmouthshire, where they are often used to explain the origins of various local landmarks.
The earliest known mention of Jack o' Kent in print comes from a sixteenth-century play, suggesting that his legend was already well established in oral tradition by that time. For many years, he also served as a bogeyman figure used to frighten children, a role that continued into the early twentieth century.
Various theories have been proposed regarding his identity. Some believe Jack was inspired by the poet Siôn Cent or even the historical rebel Owain Glyndŵr. However, it is more likely that he represents a blend of different personalities and mythic traditions from the region.
In most tales, Jack defeats the Devil by taking advantage of loopholes in the deals they strike. In one popular story, Jack agrees to share his crops with the Devil, who will ensure good weather. The Devil is allowed to choose either the tops or the bottoms of the plants. Expecting a harvest of wheat, the Devil picks the tops, but Jack plants turnips, leaving him with worthless leaves. The following year, the Devil chooses the bottoms instead, so Jack sows wheat, once again outwitting his foe.
In another tale, Jack persuades the Devil to help him build a bridge in exchange for the first soul to cross it. After the bridge is completed, Jack tosses a bone across and lets a dog run after it, thus fulfilling the deal without sacrificing a human.
Several geographical features in the Anglo-Welsh borderlands are linked to Jack o' Kent through local lore. One story claims he bet the Devil that Sugar Loaf Mountain was taller than the Malvern Hills. When Jack won, the Devil tried to increase the height of the Malverns by adding more earth, but the sack he carried tore open and spilled, forming a hill. The cleft in the western side of Skirrid is said to have been caused by Jack’s heel when he jumped from Sugar Loaf Mountain. The standing stones at Trelleck are also attributed to Jack, either thrown there by him during a stone-throwing contest with the Devil or hurled from the Skirrid in another variation.