A native of
Llansannan,
Denbighshire, Midleton entered into the service of
William Herbert, first
earl of Pembroke (d. 1570) as his secretary, subsequently serving
Henry Herbert, the second earl. At the Herberts' home of
Wilton he came to know
Sir Philip Sidney, the brother of Henry Herbert's wife,
Mary. Midleton accompanied Sidney to the
Netherlands in 1585, serving as his ensign-bearer at the
battle of Zutphen. In 1589 he participated in the unsuccessful English expedition to
Portugal. He subsequently embarked on a career as a
privateer, being recorded in October 1589 as the captain of the
Elizabeth and Mary, a ship owned by his cousin, the London merchant
Thomas Myddelton, which sailed into
Plymouth with a captured Brazilian. In 1590 he sailed another of his cousin's ships, the
Riall, capturing two argosies bound for
Lisbon from
Florence, with a cargo worth £13,000. Midleton's privateering career is perhaps reflected in a claim in a Welsh manuscript owned by
Thomas Pennant that Midleton and two companions (one of them being
Thomas Prys, another Welsh poet and privateer) were 'the first that smoaked Tobacco publickly at London'. The English writer Richard Robinson (1544/5–1603) records Midleton's privateering exploits in the ships of
George Clifford, third
earl of Cumberland (1558–1605), citing Midleton as his source for his account of eight of Clifford's privateering voyages. In 1595 Midleton sailed with
Sir Francis Drake and Sir John Hopkins as captain of the
Salomon Bonaventure in their abortive expedition to
Panama. Whilst anchored at the island of Escudo, not inhabited but full of Tarrtasis and Aligators', Midleton completed his Welsh metrical version of the psalms on 24 January 1596. Richard Robinson records that Midleton died at
Falmouth on return from Panama. == Poetry ==