After deposing King Richard II, Henry Bolingbroke has ascended the throne as Henry IV. Guilt about the desposition troubles his conscience, and the stability of his reign is threatened by growing opposition from some of the nobles who helped him to the throne. His son, Prince Hal, is living a dissolute life, frequenting the taverns of Eastcheap in the company of Sir John Falstaff and other disreputable characters. Opposition to the King becomes open rebellion, led by the Earl of Northumberland's son Henry Percy, known for his courage and impetuous nature as Hotspur. The Percy family support the claim to the throne of Hotspur's brother-in-law Edmund Mortimer. The rebellion brings Hal back to his father's side. The King's army meet the rebels at the Battle of Shrewsbury, where Hal vows to seek out and defeat Hotspur.
In 1573, three of de Vere's men set upon two of Burghley's men in Kent on the road between Gravesend and Rochester. Burghley's men wrote a letter seeking Burghley's protection. This letter represents the remaining historical record of the event. In King Henry the Fourth, Part One, de Vere gives his side of the incident. In the play, the Falstaff and his men set upon travellers at Gad's Hill (a landmark on the road between Gravesend and Rochester). Falstaff (de Vere) states:
FALSTAFF: I'll starve ere I rob a foot further. And [if] 'twere not as good a deed as drink to turn true man and to leave these rogues, I am the veriest varlet that ever chewed with tooth ... A plague upon it when thieves cannot be true to one another.
This is de Vere's apology to the Queen and Burghley for an event in the reckless period of his youth.
The historical Shakespearean plays were the product of de Vere's arrangement with Queen Elizabeth in which she paid de Vere an annuity of £1,000 and in return de Vere writes propaganda plays for the masses to promote the virtues of and loyalty to the regime.