The first voyage he made was to the West Indies, where he had the misfortune to be taken by pirates, and by them being set on shore, he was reduced almost to downright starving.  However, begging his way to Boston in New England, he from thence found a method of returning home once again.  The first thing he did was to enquire for his wife.  But she, under a pretence of having received advice of his death from America, had gotten another husband; and though poor James was willing to pass that by, yet the woman, it seems, knew better when she was well, and under pretence of affection for two children which she had by this last husband, absolutely refused to leave him and return back to Dick, her first spouse.  However, he did not seem to have taken this much to heart, for in a short time he followed her example and married another wife; but finding no method of procuring an honest livelihood, he took a short method of living, viz., to thieving after every manner that came in his way.

He committed a vast number of robberies in a very short space, chiefly upon the waggoners in the Oxford Road, and sometimes, as if there were not crime enough in barely robbing them, he added to it by the cruel manner in which he treated them.  At this rate he went on for a considerable space, till being apprehended for a robbery of a man on Hanwell Green, from whom he took but ten shillings, he was shortly after convicted; and having no friends, from that time he laid aside all hope of life.

During the space he had to prepare himself for death, he appeared so far from being either terrified, or even unwilling to die, that he looked upon it as a very happy relief from a very troublesome and uneasy life, and declared, with all outward appearance of sincerity, that he would not, even if it were in his power, procure a reprieve, or avoid that death which could alone prove a remedy for those evils which had so long rendered life a burden.  He was very earnest to be instructed in the duties of religion, and seemed to desire nothing else than to prepare himself, as well as time and his melancholy circumstances would allow him, and never from the time of his conviction showed any change in his disposition but continued still rather to wish for his death than to fear it.  He made a very ample confession of all the robberies he had ever done, and seemed sorrowful enough, above all, for the inhumanity and incivility with which he had sometimes treated people.

Amongst other particulars he said that once, with his companions, having robbed a lady in some other company of a whip, and a tortoiseshell snuff-box with a silver rim, she earnestly desired to have them returned, saying that as to the money they had taken they were heartily welcome; the other thieves seemed inclinable to grant her request, but James absolutely declared that she should not have them.  However, as a very extraordinary mark of his generosity, he took the snuff out of the box, and putting it into a paper, gave it her back again.