In the early morning hours of January 16, 1934 amid a dense fog rising from the Trinity River Clyde Barrow along with a man named James Mullens lay in a patch of weeds waiting for the line of prisoners to assemble at their work areas nearby. At 7:00 am, the prison work crew had appeared along with their customary escorts known as "longarm guards". Among them were prisoners Raymond Hamilton and Joe Palmer, both armed with loaded .45 automatics retrieved from a hiding place near a woodpile. As the prisoners reached the point near Clyde and Mullens, Ray and Palmer produced their weapons and began firing on the guards. Major Crowson fired upon Palmer, inflicting a superficial scalp wound. Palmer returned fire. One round from Palmer's pistol struck Major Crowson in the stomach, an injury which later proved fatal. Ray's bullet hit guard Olin Bozeman in the hip knocking him to the ground. Bozeman was later treated at Huntsville hospital and released. Crowson age 24 died shortly after. To cover the escaping men Barrow and Mullens jumped up from their posts and began firing their Browning automatic rifles in the air. The other prisoners not involved in the escape plan, dropped to the ground in an effort to avoid being struck in the crossfire. Meanwhile, Bonnie had remained in the black Ford V8 coupe at a distance of about one mile. Upon hearing the thundering sounds of gunfire she depressed the car's horn to guide the escapees in the fog towards the getaway car. Hamilton, Palmer, and Methvin along with two other convicts Hilton Bybee and J.B French all met up at the small Ford coupe. Just then Clyde and Mullens approached the group, hearing Raymond complaining that there wasn't enough room in the coupe to accommodate them all. Clyde retorted: "shut your mouth, this is my car and I'm handling it". Although cramped and uncomfortable, they all managed to find their places in the car. They made their way to Hillsboro by evening and with Clyde driving continued on dropping off French and Bybee before turning north toward Forth Worth.
Eventually, Raymond Hamilton broke off his ties with the Barrow gang. Bonnie and Clyde were content with the small robberies that just sustained their daily survival. Raymond however, had visions of greater wealth and big bank jobs and wasn't content with the small take from filling station hold ups. After the split, Raymond made it known in a public statement, that he was in a different league than Barrow. But what really started a riff between the two outlaws, was that when Clyde was driving, he witnessed through his rear view mirror, Raymond lining his pocket with money they had obtained from a fresh bank robbery and also handing some of this loot to his then girlfriend Mary O'Dare who was seated next to him in the back of the car. Ray stated that he was a "gentleman bandit" and not to be connected to Clyde Barrow any more. While in New Orleans, Louisiana, Raymond, along with galpal Mary O'Dare, lived the good life, staying at the Lafayette Hotel under an alias. While there, he wrote a letter on the hotel's stationary to his attorney, about his not being associated with Barrow anymore.
Called a "washerwoman" by Bonnie Parker and Henry Methvin and considered a "golddigger" by Raymond's older brother Floyd Hamilton, Mary O'Dare from Wichita Falls was not very popular with the others in the Barrow gang. Mary unsuccessfully tried to persuade Bonnie to drug Clyde, rip him off and leave him. As with Billie Parker, Mary too, was sentenced to one year and one day in the federal prison at Alderson, W. Virginia for harboring Bonnie and Clyde. Also, in 1938, Mary received a five year stint for narcotics trafficking. She was first married to a criminal, Gene O'Dare and then married to a Wichita Falls tailor named Barney A. Pitts. Mary was playing the part of "Moll" to Raymond Hamilton, but was then looking to reconcile her earlier marriage to Barney Pitts. She was also married to a criminal named Raymond Tilghman and later married convict Fred H. Holmes. She was the daughter of Joe Chambless and the sister of criminal Odell Chambless (photo below). Mary was lastly married to real estate developer Chuck Collins. Mary O'Dare Collins died at the ripe age of 95 and her ashes were scattered over the California mountains.
Following the robbery of a bank in Prentiss, Mississippi, Raymond Hamilton and Ralph Fults made good their escape in a car belonging to a M.E. Smith, taking Smith and his companion Ralph Bayless as hostages for the next 24 hours, where they were much of the time locked in the car's rear compartment. The car was later deserted on the edge of Memphis, Tenn.
Ray graduated to "Major Crime" when he met Bonnie and Clyde. During an escape from Prison, Joseph Crowson, a guard was slain. For that crime, Raymond was to die in the "electric chair." He did, on the evening of May 10, 1935 Raymond and fellow inmate Joe Palmer, were both to die that evening. Because of Raymond being so upset, Palmer agreed to go first. Raymond finally composed himself and followed. Just before the current was applied, Raymond turned momentarily to the assembled witnesses and said, "Well...goodbye all".