Wynn’s ‘weak constitution’ disrupted his education and presumably affected his chances for early advancement. In November 1611 he joined his elder brother Robert at St. John’s, Cambridge, but his stay was cut short by illness and he returned to Gwydir without matriculating, probably in the autumn of 1612.
Wynn’s post included board and lodging at the Great Wardrobe, but carried no fee, leaving him dependent upon the £40 a year which he received from his father. The alleged inadequacy of this allowance formed a regular source of friction between the two men: Wynn insisted that ‘things are now at three times a dearer rate than they were in your time’; protested that his brothers had formerly been allowed £50 a year; and complained that his father neglected to pay both his annuity and the bills for goods he had bought on credit for dispatch to Gwydir.
Wynn played only a peripheral part in the hard-fought Caernarvonshire election of December 1620. The family’s candidate, Sir Richard, incurred his father’s wrath for allowing the election writ to fall into the hands of his enemies, but Wynn recruited John Williams, dean of Westminster, an old family friend, to explain that the fault lay with lord chancellor St. Alban (Sir Francis Bacon*). With his prospects looking bleak, Sir Richard assured his father that he would be able to gain a borough seat elsewhere, and suggested that his brother William should be nominated in his stead, ‘such an affront would it be to [John] Griffith [III*] and all his abettors that it lay in your power to make one of your youngest sons his competitor, and carry it’. Wynn’s prospects of victory would have been negligible in these circumstances, but the strategy was a valid one to mitigate a humiliating defeat, and on election day Sir Richard’s place was taken by not by his brother, but by Griffith Jones of Castellmarch.
One unexpected consequence of the 1621 Parliament was the impeachment of Bacon, and the elevation of dean Williams to the keepership. When Wynn discussed his career with his father a year earlier he had envisaged continuing in service under Cranfield, who was hotly favoured to fill the vacant treasurership, ‘so by his raising I make no question but it will be some benefit unto me, and will gain me respect and good opinion in the world’. However, he conceded that ‘this shall not hinder my preferment otherwise, if ... you can hearken out a good place for me’. A year later, with the treasurership in the hands of Sir Henry Montagu* rather than Cranfield, Williams appeared to be a much better prospect, and Wynn duly transferred to his service.
It was probably Williams, an energetic electoral patron, who encouraged Wynn to stand for Caernarvon Boroughs at the general election of January 1624. Wynn applied for support to Sir William Thomas and William Griffith, his family’s closest allies on the Caernarvon corporation, and with the memory of 1620 very much in mind, he assured his father ‘I will take care to procure the writ to be sent you’. However, the fruits of his careful preparation were enjoyed by Sir Peter Mutton, chief justice of North Wales, whom his brother Owen had originally proposed for the county seat.
As a younger son, Wynn’s best prospects lay in a good marriage. In September 1620 he brushed aside his father’s suggestion for a match (either for himself or his brother Henry) with one of the daughters of John Panton*, on the grounds that the proposed bride was only 11 years old. Four years later he married an heiress, who brought him not only a modest landed estate in Merioneth and Kent, but also the profits of her recently deceased father’s droving and moneylending enterprises. One of his wife’s largest assets was a mortgage of part of William Salesbury’s* estate at Bachymbyd, Denbighshire, which may explain why Wynn’s father settled his own estate at nearby Garthgynan, worth £200 a year, upon the couple.
With his financial future secure, Williams’s fall in November 1625 was less of a catastrophe for Wynn than it might have been. He showed solidarity with his disgraced master by accompanying him to the episcopal palace at Buckden, Huntingdonshire, but soon returned to London. He presumably resigned his post at this time, although he remained alert to the possibility that Williams might return to favour at Court.
Wynn returned to Wales on the outbreak of Civil War, but was not a committed supporter of either side, and continued as prothonotary throughout all the changes of regime.