In spite of his Protestant views, Chaloner was still employed by the government, going to Scotland in 1555–1556, and providing carriages for troops in the war with France, 1557–1558. In 1558 he went as Elizabeth's ambassador to the Emperor Ferdinand at Cambrai, from July 1559 to February 1559/60 he was ambassador to Philip II of Spain at Brussels, and in 1561 he went in the same capacity to Spain. His letters are full of complaints of his treatment there, but it was not till 1564, when in failing health, that he was allowed to return home. He died at his house in Clerkenwell on 14 October 1565.
He acquired during his years of service three estates, Guisborough in Yorkshire, Steeple Claydon in Buckinghamshire, and St Bees in Cumberland. He married (I) Joan, widow of Sir Thomas Leigh; and (2) Audrey, daughter of Edward Frodsham, of Elton, Cheshire, by whom he had one son, Sir Thomas Chaloner (1559–1615). Chaloner was the intimate of most of the learned men of his day, and with Lord Burghley he had a lifelong friendship.[5]
Throughout his busy official life he occupied himself with literature, his Latin verses and his pastoral poems being much admired by his contemporaries. Chaloner wrote the tragedy of Richard II for William Baldwin's Mirror for Magistrates, first published in 1559. His most important work, De Rep. Anglorum instauranda libri decem, written while he was in Spain, was first published by William Malim (1579, 3 pts.), with complimentary Latin verses in praise of the author by Burghley and others. Chaloner's epigrams and epitaphs were also added to the volume, as well as in laudem Henrici octavi ... carmen Panegericum, first printed in 1560.[5]
Amongst his other works are The praise of folie, Moriae encomium ... by Erasmus ... Englished by Sir Thomas Chaloner, Knight (1549, ed. Janet E. Ashbee, 1901); A book of the Office of Servantes (1543), translated from Gilbert Cousin (Gilbertus Cognatus); and An homilie of Saint John Chrysostome ... Englished by T. C. (1544).[5]
In 1598 Chaloner is mentioned in Francis Meres' Palladis Tamia as a pastoral poet: "As Theocritus in Greeke, Virgil and Mantuan in Latine, Sanazar in Italian, and the Authour of Amyntae Gaudia and Walsinghams Melibaeus are the best for pastorall: so amongst us the best in this kind are Sir Philip Sidney, master Challener, Spencer, Stephen Gosson, Abraham Fraunce and Barnefield." Palladis Tamia is important in English literary history as the first critical account of the poems and early plays of William Shakespeare.[citation needed]