Macomb Train Robbery

On the evening of January 3, 1899, a westbound train was held up by about half a dozen men at Macomb, Missouri, a station along the Kansas City, Fort Scott and Memphis Railroad, a few miles east of Mansfield in Wright County. Later evidence showed that the robbers had arranged for a local man, Oscar Ray, to purchase a passenger ticket from Norwood to Macomb as a way of insuring that the train would stop at Macomb, although Ray apparently was otherwise unaware of the outlaws' plans.
When the train stopped at Macomb, Ray got off and started directly toward his home three miles into the country, while the robbers, all of them masked except one, appeared on the scene and compelled the engineer and fireman to leave the engine and go back and uncouple the passenger cars from the front part of the train. The robbers then commandeered the engine, the mail car, and the combination express/baggage car, and one of them got in the engine and drove the three cars away from the station a distance of one fourth to one half mile. Here the robbers broke into the express/baggage car, blew open the safe, and robbed it of its contents, including about $900 and several watches. The holdup men then fired a few warning shots before hurrying to their horses, which they had left about a half mile south of the track, to make their getaway.
A local farmer named Lewis Nigh and two men named Jennings and Sheppard, who were not from the area, were arrested on suspicion at Nigh's home on January 7. Nigh's son-in-law Elmer Byrum was arrested the next day, and he soon turned state's evidence, implicating another local farmer, Jake Fagley, and a man named Jack Kennedy, who had first been introduced to Byrum under the alias of Wright. Kennedy was arrested in Kansas City on January 10, and Fagley was arrested about the same time or shortly afterward in Laclede County, 65 miles from Macomb.
All six men were charged with train robbery, but young Byrum cut a deal with the prosecution and the charges against him were dropped (or at least he didn't spend any time in prison). He testified against the other defendants, naming Kennedy as the ringleader of the gang and the one who had talked the local farmers into going along with the scheme. Kennedy was from the Kansas City area and had spent some time there in the city jail, where Jennings had been one of his fellow inmates. Kennedy had at one time been a railroad engineer, and he was the man who had driven the engine away from the station at Macomb. Sheppard was also from the KC area, but he was just a 17-year-old lad.
All five defendants were convicted of train robbery and received varying sentences. Although Kennedy was supposedly the leader of the gang, Jennings received the longest sentence, twenty years in the state pen. Kennedy received a seventeen-year sentence. Both Nigh and Fagley were given twelve years, while Sheppard, probably in consideration of his youth, was sentenced to only ten years in prison.
Nigh died in prison just a year or so after being sent up, and the other four were all released early, either under the state's three-fourths rule or by having their sentences commuted by the governor.
Discharged in 1912, Kennedy went on to resume his career in train robbery. Using a similar M.O. as the Macomb robbers had used, Kennedy and a sidekick held up a train near the small community of Seventy-Six in eastern Missouri in early November 1922 as it was bound from St. Louis to Memphis. After uncoupling the mail and express cars from the passenger cars, the outlaw pair drove the locomotive and two cars down the track a ways before stopping and robbing the mail car. They then uncoupled the engine from the other two cars and drove it south, jumping from the still-running locomotive near Wittenburg, where their getaway automobile was hidden in some brush.
Unbeknownst to the bandits, postal detectives were onto their scheme and were waiting for them near the vehicle. When the two outlaws made a move for their guns, the officers opened fire, killing both desperadoes.