One day in May he and F. Benson being in Leicester Fields, Benson attempted to get a gentleman’s watch, but missing his pull, the gentleman perceived it and raised a mob.  Shepherd passing briskly to save his companion, was apprehended in his stead, and being carried before Justice Walters, was committed to New Prison, where the first sight he saw was his old companion, Bess Lion, who had found her way thither upon a like errand.  Jack, who now saw himself beset with danger, began to exert all his little cunning, which was indeed his masterpiece.  For this purpose he applied first to Benson’s friends, who were in good circumstances, hoping by their mediation to make the matter up, but in this he miscarried.  Then he attempted a slight information, but the Justice to whom he sent it, perceiving how trivial a thing it was, and guessing well at the drift thereof, refused it.  Whereupon Shepherd, when driven to his last shift, communicated his resolution to Bess Lion.  They laid their heads together the fore part of the night, and then went to work to break out, which they effected by force, and got safe off to one of Bess Lion’s old lodgings, where she kept him secret for some time, frightening him with stories of great searches being made after him, in order to detain him from conversing with any other woman.

But Jack being not naturally timorous, and having a strong inclination to be out again in his old way with his companions, it was not long before he gave her the slip, and lodged himself with another of his female acquaintances, in a little by-court near the Strand.  Here one Charles Grace desired to become an associate with him.  Jack was very ready to take any young fellow in as a partner of his villainies, and Grace told him that his reason for doing such things was to keep a beautiful woman without the knowledge of his relations.  Shepherd and he therefore getting into the acquaintance of one Anthony Lamb, an apprentice of Mr. Carter, near St. Clement’s Church, they inveigled the young man to consent to let them in to rob his master’s house.  He accordingly performed it, and they took from Mr. Barton, who lodged there, to a very considerable value.  But Grace and Shepherd quarrelling about the division, Shepherd wounded Grace in a violent manner, and on this quarrel betraying one another, they were all taken, Shepherd only escaping.  But the misfortune of poor Lamb who had been drawn in, being so very young, so far prevailed upon several gentlemen who knew him, that they not only prevailed to have his sentence mitigated to transportation, but also furnished him with all necessaries, and procured an order that on his arrival there he should not be sold as the other felons were, but that he should be left at liberty to provide for himself as well as he could.

It seems that Shepherd’s gang (which consisted of himself, his brother Tom, Joseph Blake, alias Blueskin, Charles Grace, James Sikes, to whose name his companions tacked their two favourite syllables, Hell and Fury) not knowing how to dispose of the goods they had taken, made use of one William Field for that purpose, who Shepherd in his ludicrous style, used to characterise thus:  that he was a fellow wicked enough to do anything, but his want of courage permitted him to do nothing but carry on the trade he did, which was that of selling stolen goods when put into his hands.