The brothers were being held in a cell in Indiana and forcibly removed five days after the guards death. A fourth brother John was also a member of the gang which although their reign of terror was a short one they were credited with pulling off the first train robbery in American history and theirs was the inspiration for other criminal copycats in later years.

The Reno brothers committed their first heist on October 6th 1866. They managed to stop the train outside of Seymour, Indiana and stole $10,000 in both cash and gold. They were unable to break into the safe despite repeatedly shooting at it before fleeing. They were fast in getting away from the scene of their crimes but their downfall was all the crimes they committed were in the area of Seymour, Indiana. Railroad companies hired Pinkerton detectives to find those responsible and at the end of 1867 John Reno was the first to be captured. In January of 1868 he was found guilty and sentenced to spend the next 25 years in prison.

The three remaining brothers at large continued to rob banks and trains in their local area. On May 22 1868 they stopped a train and beat the guard with pistols and crowbars before escaping with the sum of $96,000. The Pinkerton detectives hoped to lure the criminals in with a trap. A rumour was circulated about a big gold shipment on a train. When the predictable thieves stopped the train the detectives were lying in wait for them.

Once the three of them were in the hands of the mob they had no escape from what was to be their hanging. Two of the brothers accepted their fate and went quietly, the third brother Simon put up a bitter fight in an attempt to get away. During the hanging he continued to fight and survived on the end of the rope for 30 minutes before he died.