Ill-Weaved Ambition tells the story of three characters - Henry Bolingbroke, Hotspur and Prince Hal - from Shakespeare's second Henriad (Richard II & Henry IV, Parts 1 & 2) and how their ambition, or lack thereof, controlled their respective fates. The ambition of these characters is driven by their desire to surpass the achievements of their father and/or father figures. The ability of the son to surpassing his father figures,is crucial to the success or failure of their ambitions. While Shakespeare was writing about these figures, Robert Devereaux, Earl of Essex, a historical personage from Shakespeare's own time, was achieving similar successes, and failures, with his own ambitions in which he attempted to surpass the achievements of his father figures. The goal of this work is to tie the connection between Shakespeare's characters and the Earl of Essex by analyzing how their ambitions to surpass the achievements of their father figures decided their fates, whether good or bad.This is a must read for anyone who is interested in learning of the psyche of the Plantagenet and Tudor aristocrat.