John of Gaunt III's rule was becoming unpopular due to high taxation and his affair with Alice Perrers, political opinion closely associated the Duke of Lancaster with the failing government of the 1370s. Furthermore, while King Edward and the Prince of Wales were popular heroes due to their successes on the battlefield, John of Gaunt had not won equivalent military renown that could have bolstered his reputation. Although he fought in the Battle of Nájera (1367), for example, his later military projects proved unsuccessful. When Edward III died in 1377 and John's ten-year-old nephew succeeded as Richard II of England, John's influence strengthened.
Alice FitzAlan, Baroness Cherleton Eleanor of Lancaster, and her maternal grandparents were William de Bohun, 1st Earl of Northampton and Elizabeth de Badlesmere. On 21 September 1397, her father was executed at Tower Hill, Cheapside for high treason against King Richard II of England. Sometime before March 1392 Alice married John Cherleton, 4th Lord Cherleton (25 April 1362 – 19 October 1401). According to popular belief, following her marriage she became the mistress of Cardinal Henry Beaufort, and bore him an illegitimate daughter, Jane Beaufort. In Philip Yorke's "The Royal Tribes of Wales", he states that "Cardinal Beaufort left an illegitimate daughter by Alice,