His father fled abroad amid accusations of treason during the Merciless Parliament in 1388, forfeiting the title of Earl of Suffolk and the family estates.

[2] Over the next decade the younger Michael de la Pole made vigorous attempts to recover these lands, and obtained most of them piecemeal between 1389 and 1392, following his father's death.

However, his close association with the Lords Appellant, particularly the Earl of Warwick and the Duke of Gloucester prejudiced Richard II against him.

He took part in the campaign in Scotland in 1400, in naval operations around 1405, and served as the senior English diplomat at the Council of Pisa (1409).

However, he devoted most of his energies to re-establishing de la Pole influence in East Anglia.