At the time of the marriage of Sir Thomas Urquhart, senior, Lord Elphinstone, who was fully acquainted with the prosperous condition of his son-in-law's affairs, made him pledge himself to manage his property so that it might descend to his heir as he had himself received it. Unfortunately this pledge was not fulfilled. Through mismanagement and neglect his affairs got into disorder, and the later years of his life were troubled by pecuniary difficulties.[21] His son says of him: "Of all men living [he was] the justest, equallest, and most honest in his dealings, [and] his humour was, rather than to break his word, to lose all he had, and stand to his most undeliberate promises, what ever they might cost; which too strict adherence to the austerest principles of veracity, proved oftentimes dammageable to him in his negotiations with many cunning sharks, who knew with what profitable odds they could scrue themselves in upon the windings of so good a nature.... By the unfaithfulnes, on the one side, of some of his menial servants, in filching from him much of his personal estate, and falsehood of several chamberlains and bayliffs to whom he had intrusted the managing of his rents, in the unconscionable discharge of their receits, by giving up one account thrice, and of such accounts many; and, on the other part, by the frequency of disadvantagious bargains, which the slieness of the subtil merchant did involve him in, his loss came unawares upon him, and irresistibly, like an armed man; too great trust to the one, and facility in behalf of the other, occasioning so grievous a misfortune, which nevertheless did not proceed from want of knowledge or abilitie in natural parts, for in the business of other men he would have given a very sound advice, and was surpassing dextrous in arbitrements, upon any reference submitted to him, but that hee thought it did derogate from the nobility of his house and reputation of his person, to look to petty things in matter of his own affairs."[22]
One of the ways in which the elder Sir Thomas succeeded in impoverishing himself and his family was in becoming bail for people who absconded; so, at least, we would infer from an entry in the Court-book of the Burgh of Banff under date of 21st April, 1629, in which we find that "Sir Thomas Urquhurt of Cromarty, having become caution for the appearance of Alexander Forbes, merchant in Balvenye, alleged forestaller, and the said Alexander not having appeared, Sir Thomas is decerned to pay £40 Scots (£3, 6s. 8d. Sterling)."[23]