Even more than his debts, the Earl of Leicester's will triggered litigation. He had intended his illegitimate son from his early 1570s relationship with Douglas Sheffield, the adolescent Robert Dudley, to inherit Kenilworth after the death of his brother, Ambrose Dudley, 3rd Earl of Warwick. Some of the countess' jointure manors lay in the castle's vicinity, while at the same time they had been assigned to the younger Dudley's inheritance by the overseers of Leicester's will. After Warwick's death in February 1590, lengthy legal proceedings ensued over whether particular parts of Lady Leicester's jointure belonged to the Kenilworth estate or not.