On the death of Queen Elizabeth, Holles retired to the country, for though he was one of the first to wait upon King James on his coming into England he was disappointed by not being more favourably received. Some years afterwards, on Prince Henry being created Prince of Wales, Holles was appointed comptroller of his household, and this office he retained during the Prince's life, who, indeed, expressed great affection for him, and paid a visit of some duration at Haughton, where a great entertainment was provided for his amusement. But, with the death of the Prince all his favour at court came to an end. Indeed Holles is reported to have said to his friends: “There were two sorts of men King James had never kindness for, those whose hawks and dogs ran as well as his own, and those who were able to speak as much reason as himself.” A few years later he was indicted in the Star Chamber, several allegations being made against him—among others that he had had private conference with two Jesuits at their execution, and though in the opinion of those who heard him he made an excellent defence, he was committed to the Fleet prison, where he remained for some weeks; in the end, however, emerging from captivity as Baron Haughton, of Haughton. For this dignity he paid to the favourite, the Duke of Buckingham, ten thousand pounds, and on his advancement to the Earldom of Clare a further five thousand.1

His friendship with the Earl of Somerset led him to question the justice of the sentence on Weston for the murder of Sir Thomas Overbury. On the morning of the execution at Tyburn Sir John Holles, Sir John Wentworth, and others came mounted on horseback, and, as it was said, “in a ruffling and facing manner” presumed to question Weston as to whether he really was guilty of the murder of Overbury, and when they could not work upon Weston, Sir John Holles indignantly turned about his horse and said he was sorry of such a conclusion. For this offence Holles was fined £1,000.2

Holles and Sir Walter Raleigh had while at court, and as fellow-soldiers, formed a firm attachment for each other, and during the long years of Raleigh’s imprisonment, Holles, with other friends, had striven hard to save his life. He had some influence with Gondomar, the Spanish ambassador, and thought he discovered in him a disposition to appeal to the King to pardon Raleigh, if Sir Walter would entreat Gondomar to do it. But on this being named to Raleigh he paused a moment, and then said: “I am, yet, neither so old nor so-infirm, but I could be content to live, and therefore, this would I do, if I was sure it would do my business, but if it fail, then I lose both my life and my honour, and both these I will not part with.” Since his trial at Winchester for his supposed complicity with Sir Griffin Markham and others in the attempt to place Arabella Stuart on the throne, Raleigh has lain thirteen years in the Tower, and now, as related by Carlyle, “at eight o'clock on the morning of the 29th of October, 1618, in Palace Yard, Sir Walter Raleigh, a tall grey-headed man, is making his last appearance on any stage ... he has come here to die by the headsman’s axe. Sir John Holles was present. The Earl of Arundel and others in a window. Raleigh delivering his death speech, raising his voice that the spectators in the windows may hear him, they say, ‘Nay, we will come down to you, Sir Walter.’ He has smoked his last pipe of tobacco by candlelight, drunk a cup of sack; saying ‘Good liquor if a man might tarry by it.’ With a stern sympathy John Holles, the tawny deep-eyed Earl of Arundel, and the assembled thousands listen to him. And the speech ended, ‘Would you wish to go down and warm yourself a little?’ said the sympathetic sheriff. ‘Nay, good friend, let us be swift; in a quarter of an hour my ague-fit will be upon me, and they will say I tremble for fear.”

On the accession of Charles I. it was intended by the King that the two sons of the Earl of Clare (as Holles was then called) should be created Knights of the Bath; but this honour was declined by both. Nor did the Earl's younger son, Denzil, desire to take part in the Masque which was then preparing.

In 1629 Clare was again prosecuted in the Star Chamber. This time for his complicity in the circulation of a paper of advice on the establishment of absolute monarchy in England. Afterwards this prosecution was abandoned, Clare being dismissed with a reprimand, but on his refusing to acknowledge his fault he was put out of the commission of the peace for Nottinghamshire.

Whilst the Earl was in this disgrace the King made a progress into the north, along with Prince Rupert and the Prince Elector, who were then staying in England, and he remained for several days at Rufford Abbey, hunting in Sherwood Forest. The Earl being then at Haughton, only four miles away, wrote to the Prince Elector entreating him to use his influence to bring about a right understanding in the King's mind regarding him, which the Prince did, and shortly afterwards the Earl came to Rufford, and kissed the King’s hand, who promised him forgiveness—but forgot his promise.

In the latter part of his life the Earl lived principally at Haughton, and at his house in Nottingham. His daughter, the Lady Arabella, who married Sir Thomas Wentworth (afterwards Earl of Strafford), is said to have been “exceeding comely and beautiful, and yet much more lovely in the endowments of her mind”—and to her "high breeding" her portrait by Vandyke bears testimony. She died young, her death causing a breach between the Earl of Clare and her husband, Lady Clare (though mistakenly), believing that her daughter's death was owing to Sir Thomas wishing her to take a journey when in an unfit state of health.3

The death of the Earl of Clare took place at Clare Palace, Nottingham, on October 4, 1637. On the previous Sunday, after attending prayers at St. Mary's Church, he stepped aside with Lady Clare, and laying the end of his staff on the ground, said, “In this place will I be buried.” 4

John, second Earl of Clare, was born at Haughton on the 13th of June, 1595, and consequently was forty-two years of age when he succeeded to the title. During the lifetime of his father he married Elizabeth, eldest daughter of Lord Vere of Tilbury. In the last Parliament of James I. he was returned member for East Retford, and again, while still a commoner, in the reign of Charles I. under the title of Lord Haughton.

After his marriage he made a journey in the Netherlands, accompanied by his lady and her mother, to visit Lord Vere (who was then serving with the States in Holland) in his winter quarters. In a letter to his brother-in-law, Sir Thomas Wentworth, dated from The Hague, he writes: “I remember I heard you say you would send a man over hither to provide you some hawks, but it seems, having other employment for him, you have omitted it; whereupon I have taken the boldness to present you a cast by this bearer, my uncle Thomas’s ensign, a tassell, and a goss-hawk, to kill some of your pheasants at Woodhouse” (Wentworth Woodhouse, in Yorkshire), “of the fairest I could get out of Gelderland, though one of them wants some feathers. I have sent into Brabant for a lanner for you, which, if it comes, I shall bring with me, God willing, in the next man-of-war that puts off. . . . We have by chance heard of your victory in Yorkshire, whereof I am very glad.” (Sir Thomas had been chosen one of the knights of the shire.) Lord Clarendon says of this Earl: “He was a man of honour, and of courage, and would have been an excellent person if his heart had not been set too much upon the keeping and improving his estate.’

1 “Whilst the Duke lived scarce any one acquired honour but such as were either his kindred or mistresses, or paid a round sum of money for it. Nor indeed did that way of merchandise cease all the reign of our last martyred King, which was one cause, and not the least, of his misfortunes. ... I have heard the Earl inveigh bitterly against it, and he would usually call it temporal simony. I remember that once I took the liberty (hearing him so earnest on that subject), to ask him why he would purchase himself, seeing he condemned the King for selling? He answered, that he observed merit to be no medium to an honorary reward ; that he saw divers persons, who, he thought, deserved as little as he, either in their person or estates, by that means leap over his head, and therefore seeing the market open and finding his purse not unfurnished for it, he was persuaded to wear his money as other men had done” (Gervase Holles).
2 In Carlyle’s Historical Sketches is the following characteristic account of this event. “First Weston, Overbury’s appointed keeper in the Tower, is tried; and, on the 19th of October, 1615 ... is found guilty, sent swiftly to the gallows. Concerning whom I observe only this: two gentlemen ride up to him on the ladder at Tyburn. Seem to speak words with him; one of which gentlemen I seem to myself to know. Heavens! he is Sir John Holles whom I saw fencing in Sherwood Forest many years since, spoiling Gervase Markham in one important particular. He is father of the boy Denzil; has Denzil at college somewhere; a prosperous gentleman this Sir John. Markham has never forgiven him. He from the saddle speaks earnestly to Weston that he would revoke his confession, his accusation of great persons: ‘What ho, wilt thou die, doing thy kind master a disservice?’ ‘May it please you, I am going to be hanged, and seem now to be my own master. Think you, worshipful Sir John, will the great Headmaster, Maker, Creator, and Eternal Judge of us all, like me better for going to him with a lie in my mouth? Worshipful Sir John, if you come to be hanged yourself.’ Weston died, sticking to his confession; worshipful Sir John Holles and the other gentleman are tried at criminal law, get thrown into the Tower for this service, but ere too long get out again. Fain would worshipful Sir John Holles have done my lord of Somerset a service, but he could not, Death and the Devil were too strong.’
3 Clare is said to have given his children an education superior to most of the nobility;—“and he could observe nothing in them while he lived but singular arguments of comfort, save only a difference which happened betwixt his two sons, which to his dying day he could not reconcile, they being both of great stomachs. Yet the ground at the first was slight, being only a trivial difference between the wives at cards which drew in the husbands to make a party. Though something of jealousy might stick concerning their father’s affection; the Earl seeming to discover more of kindness to his younger son led to it peradventure (Gervase Holles).
4 At the time of the Earl’s death Lord Strafford wrote to the Countess “as my most beloved wife was to him, the likest of all  his lordship’s children  I have ever seen, so I ever found his justice and affections towards me, the likest hers of all the rest.” Gervase Holles writes: “By the way, I cannot but mention the most dutiful respect that I always observed in my lord of Strafford towards him, every morning and evening asking him blessing on his knee. The truth is he honoured him much, and after his death, speaking to his son, the Earl of Strafford that now is, he said, ‘Your Grandfather was a brave man; I could have spent my whole life with him, with felicity, but your uncles have used me unkindly.’”
In her widowhood the Countess of Clare was wishful to have Wentworth’s children to stay with her, but at that time he found it impossible to part with them, but in August, 1639, he consented, and wrote to her: “I thought fit to send with them one that teacheth them to write. He is a quiet, soft man, but honest, and not given to any disorder. Him I have appointed to account for the money to be laid forth, wherein he hath no direction but to pay, and lay forth as your ladyship shall appoint, and shall, as he wants, go to Woodhouse, where my cousin Rockley will supply him, and I most humbly beseech you to give orders to their servants, and otherwise to the tailor at London for their apparel, which I wholly submit to your ladyship's better judgment: and be it what it may I shall think it all happily bestowed, so as it be to your contentment, and theirs. For cost I reckon not of, and anything I have is theirs as long as I live, which is only worth thanks, for theirs, and their brothers, all I have must be whether I will or no, and therefore I desire to let them have to acknowledge me for before.”—Life of Strafford, by Elizabeth Cooper.
In a letter from Dorothy Osborne to Sir William Temple, she says of one of Strafford’s daughters, in 1653: “My Lady Anne Wentworth I hear is marrying, but I cannot learn to whom: nor is it easy to guess who is worthy of her. In my judgment she is, without dispute, the first lady I know (one always excepted); not that she is at all handsome, but infinitely virtuous and discreet, of a sober and very different humour from most of the young people of these times, but has as much wit and is as good company as anybody that ever I saw.”
She married Lord Rockingham in 1654.