Alexander C. Finley, in his History of Russellville and Logan County, Kentucky—a unique publication from the standpoint of its style—says Philip Alston was driven out of the South and settled in Logan County about 1782. A few years later “his thirst for counterfeiting again returned.” But “feeling insecure” Alston moved from place to place in western Kentucky. “About 1790 he crossed over the Ohio and became the fast friend and disciple of the notorious counterfeiter Sturdevant [Duff?] at the Cave-in-the-Rock. But he did not reside here long before he came to himself and wondered how he, the gentlemanly Philip Alston, although an elegant counterfeiter, could have become the companion of outlaws, robbers, and murderers ... and so he returned to Natchez.”[35]
It is quite likely that a counterfeiter named Duff had been making use of the Cave long before the time of Philip Alston’s short stay at the place. He may be regarded as Cave-in-Rock’s first outlaw. Neither history nor tradition has preserved Duff’s Christian name. One version suggests that he may have been the John Duff who met George Rogers Clark on the Ohio, near Fort Massac in June, 1778, and who, after some bewilderment, showed General Clark the way to Kaskaskia. It is not improbable that the two were one and the same man. At any rate, very little is known of John Duff, the guide, or of Duff the coiner.
Governor Reynolds in My Own Times and Collins, in his History of Kentucky devoted only a few lines to Duff, and these lines pertain to his death. The author of A History of Union County, Kentucky, prints some five pages on his career, based on traditions gathered in 1886. Duff apparently lived the latter part of his life in or near Cave-in-Rock and procured his lead and silver along the Saline River and in other sections of southern Illinois. He evidently operated a counterfeiter’s den in different places. According to tradition, there were at least three places known as “Duff’s Fort:” one was at Cave-in-Rock, another at Caseyville, Kentucky (near the mouth of Tradewater River, fourteen miles above the Cave) and a third in Illinois, at Island Ripple on Saline River (thirteen miles above its mouth and about twenty-eight miles, via river to the Cave). Like all outlaws of his and other times, Duff was obliged to shift his headquarters. It is probable that some of the localities in which he lived no longer have any traditions regarding his activities there.
In 1790, Philip Alston, as stated by Finley, fled to the Cave and became a “fast friend and disciple” of Duff. Collins, in his chapter on Crittenden County, Kentucky, says that Duff lived near the mouth of Tradewater River in 1799 and then, or shortly thereafter, was killed by Shawnee Indians and that “there was reason to believe some one residing at Fort Massac had employed the Indians to commit the crime.” Governor Reynolds briefly states that Duff was killed “near Island Ripple in the Saline Creek, and was buried near the old salt spring,” and that “it was supposed the Indians were hired to commit the murder.” Just where he was killed cannot be ascertained with any certainty after a lapse of so many years. There are two or three coves or small caves on Saline below Island Ripple, each of which is known as Duff’s Cave, and each has a local tradition to the effect that Duff was killed in it.
The compiler of A History of Union County, Kentucky, is the only writer who has gathered any Duff traditions, and since he confined his research to the stories told in and near Caseyville, his life of this Cave-in-Rock outlaw does not branch into the many and varied claims made in local traditions of other sections. Nevertheless, his sketch of this pioneer and counterfeiter is one that might be accepted as typical of what would be found in the other localities in which Duff had made his headquarters. In sum and substance the story runs as follows:
Duff lived in a house called “Duff’s Fort,” which stood near what later became the old site of the Christian Church in Caseyville. Here he dispensed a rude but cordial hospitality. On the bluff above was his meadow. The overhanging cliff near his house furnished a shelter for his horses. The shallow cove in which they stood is now almost filled with alluvial soil deposited by the little brook which flows near. His household consisted of his wife and a faithful black slave named Pompey, who would risk anything or undergo any hardship for his master.
It is said that Duff was a brave man and a good strategist; he was seldom found at a disadvantage. He often had narrow escapes in his encounters with the officers of the law and the people living in the vicinity. On one occasion, when he was closely pursued by his enemies, he ran towards his home. There he found his wife at the river doing the family washing. Near her was a large iron kettle, in which she was boiling clothes. Without hesitation Duff upset the kettle, rolled it into the stream, where it was quickly cooled, and lifting the kettle over his head, he plunged into the water. The river was low at this point, enabling him to wade most of the way to the farther bank. Before he reached the Illinois shore, however, his pursuers appeared on the Kentucky side and opened fire. Their aim was well directed. Several of the bullets struck the kettle, but rebounded without injury to the man beneath. On reaching the dry land he took the kettle from his head. Holding it behind him as continued protection, he ran for safety. The pursuers increased their fire. More bullets rained upon the impromptu shield—but Duff escaped unhurt to the shelter of the woods.
On another occasion when sorely pressed he took refuge with a Mrs. Hammack, who was an old-time Methodist living in that part of the country. She treated him so kindly that he decided to let her have a glimpse of his hidden treasures. On the appointed day he blindfolded her and his wife and led them by a very circuitous route to a cave. After they were in the mysterious cave he removed the bandages from their eyes and, by the light of torches, the two women were enabled to see the large quantities of counterfeit silver and gold coins in boxes and chests stored by Duff. He then replaced the bandages and took the two women back to Mrs. Hammack’s house. Mrs. Hammack’s impression was that the cave ran into the side of a cliff but, notwithstanding many efforts, she was never able to retrace her steps to the place. Mrs. Duff related, after her husband’s death, that he had taken her from their home to the cave on another occasion and in the same manner. He then promised her that he would some day show her the way to his cave, but explained at the time that he could not then do so, for his enemies might torture her into a disclosure of his location when he was in it. His intentions were frustrated by his sudden death. There are three different accounts of Duff’s death given by local tradition.
One version has it that he was killed by some of the citizens of the county, near the bluff where he quartered his horses. According to this account, a number of men were pursuing him and when he showed fight they were obliged to shoot him. Another says he was killed by Indians with whom he had quarreled about a dog fight. The following is the version most widely accepted:
Duff, three of his associates, and his slave Pompey, while in Illinois securing white metal, were surprised by about six soldiers sent from Golconda, Illinois, or some other point below Cave-in-Rock. The counterfeiters were captured and taken down the river in a boat. Handcuffs were placed upon all the white prisoners. Pompey had not been manacled because the soldiers carried only four sets of irons and, furthermore, they presumed the negro cared little whether his master was doomed. Near Cave-in-Rock they stopped for dinner. When they landed, all the soldiers went ashore except one who was left in charge of the prisoners and the boat. After stacking their arms near the boat, they went into the Cave to build a fire and prepare the meal.