|Robert Pitt as a child (attributed to Sir Peter Lely)|
William Pitt the Elder (1708-1778) had difficulty managing his purse from an early age. These monetary troubles began when he was at Eton, and became steadily worse as he went on to Trinity College in Oxford. Of course, the man paying for these early expenses was his father Robert Pitt, Esq. (c. 1680-1727). It seems Robert questioned his son on his bills, as the subject of money comes up repeatedly in their correspondence.
In about 1726, William wrote to his father Robert from Trinity College. He spent the majority of the letter explaining to his father why his expenditures were necessary, and then asked for more money:
I rec:d yrs of ye 25th in which I find with ye utmost Concern ye dissatisfaction you Express at my expense. To pretend to justify, or defend myself in this Case would be, I fear, with reason thought impertinent; tis sufficient to convince me of the Extravagance of my Expences, that they have met with yr disapprobation. But might I have leave to instance an Article or two, perhaps you may not think ‘em so wild and boundless, as with all imaginable uneasiness, I see you do not at present. Washing £2:2:0 about £3:6d per wk of which money half a dozen shirts at 4d each comes to 2s per wk shoes and stockings 1:19:0. Three pairs of shoes at 5s each two pair of stockings, one silk, one worested [sic], are all that make up this Article, but be it as it will, since Sir, you judge my Expense too great, I must endeavour for ye future to lessen it, & shall be Contented with whatever you please to allow me. One Considerable Article is a Servant, an expense which many are not at, and which I shall be glad to spare, if you shall think it fitt, in hopes to Convince you I desire nothing superfluous; as I have reason to think you will not deny me what is necessary. As you have been pleas’d to give me leave, I shall draw upon you for 25£ as soon as I have occasion. I beg my Duty to my Mother & am with all possible respect, Hon:ed Sr, Yr most Dutifull Son, W Pitt." 
Then on January 20, 1726/7, Pitt wrote to his father from Trinity College, once again on the subject of overspending. After writing a long list of his accounts, he writes, “…I have too much reason to fear you may think some of these Articles too extravagant, as they really are, but all I have to say for it is humbly to beg you would not attribute it to my extravagance, but to ye custom of this Place, where we pay for most things too at a high rate. I must again repeat my wishes for yr health, hoping you have not been prevented by so painfull a delay of ye Gout from pursuing yr intended journey to Town…" 
Robert Pitt died several months later, but his son's spending habits deteriorated further. By the time he was to marry Lady Hester Grenville in late 1754, the forty-six year old William was only half-joking when he wrote that "my infirmities and my Poverty are my best titles." 
The cycle of financial extravagance would repeat itself again in William Pitt the Elder's three sons.
Many years later, Mrs. Pretyman-Tomline would write that William Pitt (the younger) was led into debt by “…the force of example and the want of precept."  The example Lord Chatham gave to his children regarding the use - or misuse - of money would leave a lasting impression. This nonchalant approach to money and debts was already being felt by his children in the mid-1770s. As usual, the person who bore the responsibility for picking up the pieces was their mother Hester, the Countess of Chatham.
On April 8, 1777, Lady Chatham was forced to write a letter to Lord Chatham's nephew, Mr. Thomas Pitt, begging him for money. Her fifteen year old son James Charles Pitt, then in the navy, had accrued debts which she could not afford to pay:
“…A circumstance has happen’d, which is as Painful as it was unexpected. The confidence I have in your taking an affectionate share in whatever concerns my Lords situation, and Feelings, makes me suffer less in finding it indispensable to me, to address my self to you, and recur to your Friendship. Our Son James, who for many Months has been station’d at Gibraltar, by an imprudence, pardonable only in Fifteen [James was 15 years old at the time] has run into a most unfortunate excess of Expence, and such as occasions a distress to me that deranges every Provision that with the utmost Attention, and the greatest difficulty to my self, I had been able to make to answer the different Calls of my Lord’s Illness, which you must know are of a very expensive kind. The Bills Drawn, of which I have receiv’d Notice, are to an Amount that I am ashamed to name. Every proper Precaution was taken at his going out to guard against such a circumstance happening, by not allowing Him [James] to draw without his Bills being indors’d by his Captain. But the ship cruising very little, and He being suffer’d to be too much on shore, He easily got from the Dealers in the Town every Article of Dress, &c, without Payment of ready Money, so that when the Time came for his exchanging from the Alarm Frigate, into the Surprise Captain Linzee, in order to sail for Newfoundland, he would not have had it in his Power to have left Gibraltar, had not Lieut. Hood, then in Harbor, android’s bills upon his own Banker for the necessary sum to put him at Liberty, which he did out of respect to the Family, and in so doing has indeed conferred a real obligation. We are every one of us equally surprised at this Conduct in James, as he had been remarkable for his Prudence on the Subject of expence, and was all acquainted with the reasons that required he shou’d be so. Genl Boyd out of Regard to his [James’s] Father, made him free of his House whenever the ship was at Gibraltar. This led him continually into Balls Assemblies, and Parties, which I imagine caused his being so cruelly indiscreet; and not paying directly, he was not aware, I dare say, of the extent of his Expence. This Accâblement, after the trials I have had so long to contend with, makes me like one astonish’d by a Blow. I don’t know where I am, for it is of the utmost importance to my Lord’s Recovery that he should not be acquainted with this circumstance. Is it possible my Dear Sir that you cou’d lend me your Friendly Aid on this occasion. It is what I wish to ask of you, and what I flatter my self without my explaining, at Present, further, you will think me not wrong in doing. I trust I shall have your confidence that in every thing I do, I am instigated by the most serious consideration of what is necessary, to be either avoided, or follow’d for the Great End of my Lord’s Recovery, of such infinite consequences to his Family and Friends. My Wish is, if it can be without too much inconvenience, that you wou’d allow me to draw upon your Banker, as far as a Thousand Pound. This will be more by half than the Demand, come to my knowledge, but it has distress’d me so thoroughly that I shall not feel at Ease without a reserve for fear of any accident, or as (thank God), my Lord, by being better, may think of a Journey, or something that may make an immediate call…" 
Mr. Thomas Pitt must have responded favourably to her request for money, because she pens him an obliging letter on April 18, 1777:
“My Dear Sir,
The Kindness of your Letter, in answer to mine, is such as makes me feel it impossible to find expression to thank you for it, in a manner that agrees with the sense I have of it. You have added to the essential obligation I have to you for granting my request, a hundred Pleasures, to which my mind has the greatest sensibility. You have indeed render’d the Favour you have conferr’d upon me, compleat entirely…[she is ill with a cold and cough] I have writ an admonitory Letter to my Son James, which I flatter my self will have the wish’d effect, and bring his mind, notwithstanding its Ardent and Lively Turn, to a right sense of his Errors, and the impropriety of his Conduct…" 
Unfortunately, it was always Lady Chatham begging for loans in order to avert financial ruin. This cycle would repeat itself in her sons William and John, the second Lord Chatham, as they were borrowing by 1779.
1. William Pitt (the Elder) to his father Robert Pitt, Esq. April 29 [no year, but mid-1720s]. The British Library, Dropmore Series 2 - 69288, f. 10.
2.William Pitt (the Elder) to his father Robert Pitt, Esq. January 20, 1726/7. The British Library, Dropmore Series 2 - 69288, f. 18.
3. William Pitt (the Elder) to his sister Ann Pitt. October 25, 1754. The British Library, BL Add Ms 69289 873B, f. 71.
4. Elizabeth Pretyman-Tomline to her husband, the Bishop of Lincoln. Undated, but around late January 1806. Ipswich Record Office, Pretyman MSS. HA 119: T99/26.
5. Lady Chatham to Mr. Thomas Pitt. April 8, 1777. The British Library, Dropmore Series 2 - 69288, ff. 64-66.
6. Lady Chatham to Mr. Thomas Pitt. April 8, 1777. The British Library, Dropmore Series 2 - 69288, ff. 68-69.