Samson’s union to Margaret Fynes, Baroness Dacre (1541–1612) took place around 1565, when Samson was 20 years old. However, he did not acquire the title of Lord Dacre during his life. Unfortunately for Samson, his wife died before the acceptance of his claim to be called to the House of Lords. The title was passed to one of the couple’s sons, Henry Lennard (1570–1616), after the death of his mother. Samson Lennard lived in an extravagant manner, which forced him to sell some family properties between 1599 and 1614. These were some of the properties that his father, John Lennard (1508–1590) had bought around 1553. This painting has inscribed: 'Sampson Lennard, Esq / Son and Heir of John Lennard of Chevening in Kent, Esq'. The Flemish painter Marcus Gheeraerts the younger was among the most important portraitists in England at the time of Elizabeth I and did some decorative works at court.