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 Cuff his plans before Sir Henry Neville, who had just been recalled from the French embassy and had grievances against the government; and obtained Essex's consent to communicate with his old friend, Sir Charles Danvers [q. v.] Cuffe had no clear ideas as to the details of his policy, and did not take part in the secret meetings of Essex's friends, whom he had helped to bring together, at Drury House, in November and December 1600. Meanwhile some of Essex's relatives perceived the evil effect on Essex of Cuffe's maladroit counsels, and they induced him in November to dismiss him from his service. Sir Gilly Merrick, Essex's steward, was ordered to remove him from Essex House. But Cuffe appealed to the good nature of his master's friend, the Earl of Southampton, who readily obtained from Essex a rescission of the order. Cuffe's work was, however, done. He opposed the appeal to force and took no part in the riot in the city of London on Sunday, 8 Feb. 1600–1 [see, second ], but with Essex and all his allies was thrown into the Tower. When Essex, just before his execution, requested to be confronted with Cuffe in the Tower (21 Feb. 1600–1) in the presence of witnesses, he used the words: ‘You have been one of the chiefest instigators of me to all these my disloyal courses into which I have fallen.’ At the end of February Cuffe answered several questions respecting Essex's negotiations with King James of Scotland which the lords of the council put to him. He appears to have told the truth, but his replies show that he had not managed that part of Essex's correspondence, which was mainly in the hands of Anthony Bacon [q. v.] Some days before his execution, however, he wrote to Sir Robert Cecil enclosing a copy of instructions which Essex had prepared for presentation to the Earl of Mar, an ambassador to Elizabeth from James, with the object of so poisoning Mar's mind against Cecil and his friends that Mar might communicate suspicion of them to the queen. On 2 March 1600–1 Cuffe was twice re-examined, and explained his negotiation with Sir Henry Neville. Three days later he was put on his trial, with Sir Christopher Blount [q. v.], Sir Charles Danvers, Sir John Davis, and Sir Gilly Merrick. Cuffe and Merrick were not indicted, like the rest, for open acts of violence. Coke, the attorney-general and prosecuting counsel, denounced Cuffe in the strongest terms, and began his address to the court with the remark that he ‘was the arrantest traitor that ever came to that bar,’ ‘the very seducer of the earl,’ and ‘the cunning coiner of all plots.’ Cuffe replied that he had wished to see his master recalled to the queen's favour, but that was the limit of his desire and action. On the day of the rebellion he never left Essex House. Coke thereupon said that he would give him ‘a cuff that should set him down,’ and read extracts from Essex's and Sir Henry Neville's confessions. Sir Charles Danvers's confession was also put in, and it was stated that, in case of the plot succeeding, Cuffe had been promised the speakership in the next parliament. The jury returned a verdict of guilty against all the prisoners. Cuffe asked for the companionship of a divine before he was executed. On 13 March Merrick and Cuffe were drawn to Tyburn. Cuffe began a speech admitting his guilt, but denying many of the charges brought against him. The authorities twice interrupted him, and on the second occasion he ‘began to apply himself to his devotions, which he managed with a great deal of fervour,’ and ‘was despatched by the executioner’ (State Trials, i. 1410–1451). Bacon, in the official ‘Declaration of the Treasons,’ 1601, describes Cuffe as ‘a base fellow by birth, but a great scholar, and indeed a notable traitor by the book, being otherwise of a turbulent and mutinous spirit against all superiors.’ Francis Osborn, in his ‘Advice to a Son,’ illustrates by Cuffe's career his warning ‘Mingle not your interest with a great one's.’

In 1607 an editor who signed himself R. M. dedicated to Robert, lord Willoughby and Eresby, a short philosophical and scientific tract by Cuffe. Its title ran: ‘The Differences of the Ages of Man's Life: together with the Originall Causes, Progresse, and End thereof. Written by the learned Henrie Cuffe, sometime fellow of Merton College, Oxford, An. Dom. 1600 … London. Printed by Arnold Hatfield for Martin Clearke,’ 1607. Cuffe here shows wide reading in the writings of the Greek philosophers; a belief in astrology, and faith in a divine providence. Other editions appeared in 1633 and 1640. In Cott. MS. Nero D. x. is ‘De Rebus Gestis in sancto concilio Nicæno,’ a translation attributed to Cuffe from the Greek of Gelasius Cyzicenus. In Harl. MS. 1327, fol. 58, are to be found ‘Aphorismes Political, gathered out of the Life and End of that most noble Robert Devereux, Earle of Essex, not long before his death,’ a work which is also ascribed to Cuffe. Cuffe assisted Columbanus in his edition (p. 2, Florence, 1598) of Longus's ‘Pastoral of Daphnis and Chloe,’ and contributed six Greek elegiacs to Camden's ‘Britannia.’

[Wood's Athenæ Oxon. (Bliss), i. 703–9; Wood's Fasti (Bliss), i.; Wood's Antiquities, ed. Gutch, ii. 249, 250, 853; Spedding's Life of Bacon, ii. passim; Letters