The Great Rondout Train Robbery – Part One

The eight-man crew that pulled off this feat included professional thieves and a corrupt law enforcement officer; it was rumored at the time that they possibly even had mafia connections.  The caper itself was bold, simple and, with some inside information, relatively easy to pull off.  Of the people involved the most famous were probably the Newton Brothers. The four brothers (Willis, Joe, Willie and Jesse) were from Texas and had made a very profitable career of holding up banks and robbing trains. The Newtons aren’t as notorious as other outlaws, the reason probably being is that they never killed anyone in their illegal activities. As they saw it, they were into an alternate form of a business. They simply weren’t killers.

In the early twentieth century, trains were known to carry loads of cash and other valuables for the Post Office for their pay roll and other financial needs.  Hitting the right train could mean the score of a criminal’s career allowing them to retire very wealthy men. One would just need to know which train to rob.

William Fahy was thought to be a rising star among the inspectors of the Postal Service. However, he would give the robbers the date, place and time that the train loaded with goods would be. Also involved were Brent Glasscock, James Murray and Herbert Holliday. Glasscock was thought by some to be the brains of the operation. He and Murray had legal and illegal dealings with the Post Office and railroad delivery of mail. Glasscock would provide valuable information to make the robbery run smoothly and Murray would provide the place to sort and divide the stolen goods. Hebert Holliday was a volatile career criminal, who had pulled off a handful of robberies. All three possibly had connections with the mafia, most notably infamous Chicago mobsters, Dion O’Banion and Hymie Weiss.

Around 10 p.m. on the night of June 12, the Chicago, Milwaukee, St. Paul line train slowed down right outside the town of Rondout to pick up their orders from the order hoop located on the Rondout Tower. That was the signal. Willis Newton and Herbert Holliday walked out from behind their hiding place dressed as railroad workers, holding red lanterns to get the train to stop. The rest of the gang had arrived driving stolen Cadillacs. They lined the cars up to provide light for the robbers to see what they were doing, as the surrounding area was open county.

After forcing the engine crew to stop the train, they started corralling everyone outside. Staff in the other cars turned off the lights and locked the doors of their cars, per postal regulations. The thieves had accounted for this and broke or shot out the windows of the cars and threw in canisters of tear gas to force the crew inside to open their doors.  At that point everything was going according to plan. The thieves had stopped the train and were about to unload the precious postal bags into the four stolen cars That’s when everything started to unravel.