His contemporary Froissart[1] portrays de la Pole as a devious and ineffectual counsellor who dissuaded King Richard II from pursuing a certain victory against French and Scottish forces in Cumberland and fomented undue suspicion of that king's uncle John of Gaunt, 1st Duke of Lancaster.

[2] He was the eldest son of Sir William de la Pole (died 1366), Chief Baron of the Exchequer, a wool merchant from Kingston upon Hull who after the collapse of the Florentine banker families of Bardi and Peruzzi emerged as the chief financier of King Edward III.

Michael enjoyed even greater popularity at court than his father, becoming one of the most trusted and intimate friends of Edward's successor, Richard II.

He was appointed Chancellor in 1383,[3] and created Earl of Suffolk in 1385, the first of his family to hold any such title (the earldom had become extinct in 1382 on the death of William de Ufford).

[citation needed] After the Appellants' victory at Radcot Bridge (December 1387) and before the Merciless Parliament met in February 1388, de la Pole shrewdly fled to Paris, thus escaping the fate of Sir Nicholas Brembre and Chief Justice Robert Tresilian.