Saddled with the debts of his deceased father, Jacob Aemilius Irving left his family's sugar estates in Jamaica in July, 1809, to try to right his affairs. Traveling first to New York, to renew commercial contacts and try the waters at Ballston Spa, Irving was greeted with the disconcerting news that he was to be arrested for nonpayment of debt, the result of losing an old lawsuit recently revived by the mercantile firm of Moulton & Livingston. Rescued by his business associates, the Gansevoorts, Irving settled with Moulton & Livingston and continued on to Charleston, S.C., to bring his three sons home to England with him. "Not at all satisfied with the state of Education" in Carolina, Irving wished to provide the children with better schooling, but added tartly that he did not wish them either "to imbibe a partiality for this Country!" (to Joseph Birch, 1810 April 26).
In July, 1809, Irving left for Liverpool. Although professing to "shrink with horror" when thinking of the "disasters, and distresses of various branches of my poor Father's family" (1809 September 13 to Capt. Jackson), Jacob had little inkling of what the "various branches" held in store. Within a year of his arrival in Liverpool, he was called upon to bail out a nephew, James, who had been imprisoned for an enormous debt of over £4,000, accrued through scandalously high living. At considerable personal expense, Jacob assisted in James' liberation from prison during the summer of 1811, and arranged for his nephew to work off his debt in Jamaica -- though he held little confidence in James' success. Jacob wrote that his "unfortunate" nephew had "seen so much of the dissipation of fashionable life, we are not to expect much steadiness from him, although he professes to be determined in working his reformation by oeconomy & an attention to the business of planting &c.," adding parenthetically, "At any event it is better he should go out, than remain here a certain prey to his Old Associates..." (1811 November 8 to Alexander Peterkin). In a separate letter to his clerk, J. Pigot, Jacob suggested that the wine on the estate should be well hidden. To Jacob's credit, James proved just as unsteady as feared, and even more underhanded. James' ongoing efforts to gain a share in the receivership vexed Jacob so highly that he was finally forced to cut off his nephew entirely in March 1813.
Another profligate nephew, Capt. John Jackson, turned up in England as well, and grew into an even more serious financial liability. Beginning with his instance that he be allowed to borrow money against his paltry annual income from the hire of some "inferior negroes" he had inherited, Jackson continually pressed claims upon Jacob's pocketbook. Exasperated, Jacob scolded Jackon that he had "never in any transactions with any of my family met with anything but ingratitude and discontent" (1809 November 5 to John Jackson), and from there, his relations with Jackson devolved into a round of litigation and personal animosity.
Irving's troubles were not restricted to family. The American embargo of 1807-1809 cut into his trade, and the vicissitudes of the British market played havoc with Irving's plans, particularly after the Lords' rejection of the distillery bill of 1811 resulted in a string of failures among London merchants and a drop in sugar prices. Compounding these problems were the loss of ships at sea and, in 1811, a loss he could "ill afford" to arson at the port of Montego Bay. Unlike some of his correspondents, Irving did not agree that the fire was the work of people of color, seeing himself rather as a victim snared in a web spun of international silk:
"It is highly expedient in the Magistracy to offer large rewards for apprehending any Persons who may have designedly perpretrated such a flagitious act -- As to the Negroes or People of Colour they have no view, no object to answer in such a measure, unless insurrection accompanied it -- which was not, nor likely to be the case -- No! The evil originates among a parcel of wretches that creep into the country by Cuba -- Outcasts of all sorts -- Spaniards, French, Portuguese, Yankees, Jews &c &c -- and as there have been attempts since to do the like, it is presumed it is not an accident" (1811 August 6 to Alexander Peterkin)
Through this troubled period, Jacob's largest creditor, Joseph Birch & Co. of Liverpool, remained favorably disposed toward Irving and little inclined to extreme measures. By 1816, Irving appears to have worked himself free of at least some of his debts, and may have begun to resolve some of the family strife that had plagued him for so long.