It is more than likely that Mason had committed a number of crimes along the Natchez Trace before he appeared in New Madrid in March, 1800. Many pioneers traveling over this route encountered highwaymen, but none of them succeeded in identifying the men by whom they had been robbed. The first record of a case with which Mason is definitely connected is that of a party of boatmen riding from Natchez to their homes in Kentucky. An account of this incident is told in Old Times in Tennessee, by Josephus C. Guild, who received his information from John L. Swaney. Swaney told Guild that more than fifty years before, while carrying the mail over the old Natchez Trace, he frequently met Samuel Mason and talked with him.
Swaney began carrying the mail over this old Indian trail about 1796 and was familiar with the route before Mason appeared on the scene. The distance from Nashville to Natchez he estimates at about five hundred and fifty miles. It was, in his mail-carrying days, a mere bridle path winding through an almost endless wilderness. He rode it for eight years, making a round trip every three weeks. Traveling at the rate of about fifty-five miles a day permitted him a day’s rest at either end of his route. He frequently met Indians along the Trace. At Colbert’s Ferry, on the Tennessee River, he always found the Indian ferrymen “contrary,” for they would not cross the river for him if he got to the landing after bed time. At the Chickasaw Agency, about half-way between the two places, he changed horses. The only white men he saw were the few settlers, scattered forty or more miles apart, the occasional traveler returning north and, now and then, Samuel Mason and some of his band. Swaney rode a good horse and carried with him, besides the mail (consisting of a few letters, newspapers, and government dispatches) a bushel of corn for his horse, provisions and a blanket for himself, a pistol, a tin trumpet, and a piece of flint and steel.
Merchants and boatmen brought their provisions and other necessities on pack-horses or pack-mules. It was from these that Mason captured much of the food and most of the clothing he and his people required. These travelers, as a rule, sewed their money in rawhides and threw the hides in the packs with supplies. At night, before making a fire, they hid their valuables in the bushes some distance from the camp in the event of a surprise at night by robbers. It was in this wilderness that Mason looked for and found many of his victims. He and his band were the terror of all who traveled through the Indian nation, except Swaney.
Mason frequently sought interviews with Swaney, with whom he had many friendly chats. The outlaw often asked what was said about him by the public. He told Swaney that no mail-carrier need fear being molested by him and his men, for mail was of no value to them, and that he “did not desire to kill any man, for money was all he was after and if he could not get it without taking life, he certainly would shed no blood.”
“Among Mason’s first robberies,” continues the historian who interviewed the mail-carrier, “was that of a party of Kentucky boatmen returning home from Natchez. They had camped at what was called Gum Springs, in the Choctaw Nation. They ate supper, and, as a matter of precaution, were putting out pickets before retiring for the night. In going to their positions one of the pickets stepped on one of Mason’s men, who were hidden in the grass awaiting an opportunity to pounce upon the boatmen. The robber thus carelessly trod on jumped up, gave a yell, and fired off a gun, calling upon his comrades to shoot and kill every boatman. This was so unexpected to the Kentuckians that they became panic stricken and ran off in the wildest confusion, leaving everything, some even their wearing apparel. Mason and his men went to the camp and carried away everything.
“The next morning, just at daylight, Mr. Swaney came along, and seeing the camp fires burning, rode out, but could find no one. He was going toward Natchez, and having met no party that morning, he instinctively knew that something was wrong, and began to blow his bugle. The boatmen recognized the familiar sound and commenced coming to Mr. Swaney, one and two at a time. He asserted that they were the worst scared, worst looking set of men he ever saw, some of them having but little clothing on, and one big fellow had only a shirt. They immediately held a sort of council of war, and it was unanimously agreed to follow the robbers and recapture their property. It was an easy matter to follow their trail through the cane and grass. Their plan was, as they had no arms, to provide themselves with sticks and knives, and should they overtake Mason and his men, attack them by a vigorous charge, knocking them down right and left with their shillelahs, and if those in front fell at the fire of the robbers, those in the rear were to rush upon, overpower and capture the robbers and recover their property.
“They started in pursuit of the robbers under the lead of the big Kentuckian. They had gone about a mile when they began to find articles of clothing which had been thrown away by the robbers. The big Kentuckian found his pants, in the waistband of which he had sewed four gold doubloons and, to his great joy, the robbers had not found them. After this it was noticed that the big Kentuckian’s valor began to fail him, and soon he was found in the rear. The pursuit was kept up about two miles further, when they were suddenly hailed by Mason and his men, who were hid behind trees, with their guns presented, and who ordered them to go back or they would kill the last one of them. This caused a greater stampede than that of the night before, and the big Kentuckian out distanced the whole party in the race back to camp. They abused the big Kentuckian at a round rate for his want of courage, but he only laughed at them, saying he had everything to run for. But, to his credit be it said, he spent his last dollar in procuring supplies for his comrades.”
Mason was an active man and this comparatively insignificant robbery was doubtless preceded and followed by others of greater consequence of which, however, no written record or oral tradition now exists. Then occurred the Baker robbery on the old Natchez Trace—a robbery that became widely known through the current newspapers and soon convinced the public that Mason was an outlaw of dangerous character, working over a large territory.
Colonel Joshua Baker, the victim of this famous robbery, was a merchant living in central Kentucky. In his day he made a number of trips south, going down in flatboats and returning by way of the old Natchez Trace. Colonel Baker had the misfortune to come in contact with Mason at least once on land and once on water, and, as is later shown, played an important part in the activities that resulted in ending Mason’s career.
In the spring or summer of 1801, Colonel Baker took several flatboats filled with produce and horses to New Orleans. After disposing of his cargo, he set out on his return home, accompanied by four men, each of whom rode a horse. Besides the five riding horses there were five pack-mules in the cavalcade loaded down with provisions, and, among other things, the proceeds of the sales made in New Orleans. Colonel Baker and his men experienced no unusual trouble until they reached the ford across what was then called Twelve Mile Creek, but since known as Baker’s Creek. The place is in Hindes County, Mississippi, about twenty miles west of Jackson and near where the Battle of Baker’s Creek was fought on January 16, 1863. There, August 14, 1801, the Baker party was surprised by Samuel Mason and three of his men. A paragraph relative to the robbery that followed was published in The Kentucky Gazette, September 14, 1801. It is the earliest printed record so far found of Mason’s activities on the Natchez Trace: