During the early 1620s May befriended the courtier, poet and diplomat Thomas Carew, who contributed a poem to the published text of The Heir in 1622, and probably also Philip Massinger.
Massinger wrote at least one play for the short-lived Revels company (The Virgin Martyr, with Thomas Dekker) and shared May's generally Roman interests.
The 1627 edition boasted dedications of Books II to IX to prominent English noblemen, many of whom were actual or suspected opponents of Charles I's ongoing attempts to tax without Parliament.
In June 1627 May composed a poem celebrating Charles I as absolute ruler of the seas, probably as part of the upswell of support for the Isle de Rhé expedition.
May's tragedies are modelled on Jonson and are also plausibly influenced by Massinger; they concentrate on political themes, rather than erotic passions; Cleopatra and Antigone draw linguistically and thematically on Lucan.
In dedicating his Georgics May even turned to a fellow alumnus of his old college, Sir Christopher Gardiner, a well-known Catholic philanderer who left shortly afterwards for the New World – hardly the best prospective patron.
After the Restoration the then Earl of Clarendon, Edward Hyde, recorded that before the Civil War he and May had belonged to a close-knit circle of lawyers and writers grouped around the heavyweight figure of Ben Jonson.
Their shared poetic concerns also surface in a short treatise written by Digby on Edmund Spenser (Elizabethan author of The Faerie Queene), apparently at May's request.
Befitting a major work of Neo-Latin poetry it was published in Leiden, one of the centres of continental humanist scholarship, and received dedications from a number of Dutch intellectuals including Marcus Zuerius van Boxhorn and Nicolaus Heinsius.
Letters from Heinsius's father Daniel to Patrick Young, the Royal Librarian, and John Selden indicate that May wrote the translation while in the Netherlands (on what business is unclear).
It contained harsh criticism of princes (like Charles I) who had sought to rule without consulting Parliament, but also warned against allowing the people too much responsibility, equating popular government with damaging innovation and turbulence.
May emerges in this work, his only explicit statement of political analysis or belief, as a cautious and conservative thinker, distrustful of awarding too much power to any one body, and therefore implicitly a constitutionalist Parliamentarian.
A shining example of rhetorical humanist historiography, complete with plentiful classical citations (especially from Lucan), May presented recent English history as the wrecking of a peaceful and prosperous Elizabethan polity by the greed and stupidity of the Stuarts.
In October 1649, following the regicide and the emergence of an English republican government, May contributed a dedicatory epistle to Charles Sydenham's attack on the Leveller John Lilburne, addressing the members of the Rump Parliament, Roman style, as 'Senators'.
He dismisses Lilburne and fellow democratic agitators for having no landed interest in the kingdom (echoing the position taken up by Ireton in the Putney Debates of 1647) and warns MPs to heed the 'better sort'.
In 1650 May published a revised history of Parliament eschewing (for the most part) classical citations and other rhetorical adornments in favour of a curt, Sallustian Latin prose style.
The republicans Henry Marten and Thomas Chaloner were charged by the Council of State with seeing to May's 'burial', setting aside £100 for the purpose, and both men and Sir James Harrington with finding a replacement historian of Parliament.