The best guess may be that he and Roy mingled and identified with friendly, turn-of-the-century gamblers, drifters and hoboes, those admired men of ease and freedom who played billiards and bet on horses at the racetracks. The mythos that emerged around this lifestyle must have taken hold of their souls, even though the results would not be apparent until much later in life. Like neglected children the world over, they looked outside of their family for sustenance and in the morally milder times in which they grew up, they gradually came to learn that they could beat the odds no matter how much was stacked against them. After Ray enlisted he did not see his brother again for some thirty years. They were to be reunited by Roy's wife, Helen Purcell Myers, who had been a concert pianist. Roy was then the owner of a poolroom, while Ray had come to love poker and horse racing. Roy had suffered a serious accident and had a glass eye.

Early military records of Private Myers reveal the following: Company M, 28th Infantry from 4-24-11 to 4-23-14; Company B, 27th Infantry 8-15-14 to 3-16-17 (Philippine Islands). During the second enlistment a significant emergency assignment was with the Punitive Expedition of 1916, led by Brigadier General John J. "Black Jack" Pershing. The aim was to "get Villa," or Pancho Villa (1878-1923), bandido of the Mexican revolution. The history and details of this expedition were published in the Elks Magazine, in February 1989, by Raymond's son, John, and is reprinted in this section in part on page 20. Raymond would learn he was not a natural fighter or infantryman ("I had a glass jaw," he would say) and by his third enlistment the army proved accommodating and gave him other assignments. He would always consider the army "fair," in addition to providing "three square meals a day." A story he related about his fellow soldiers in the Punitive Expedition is very interesting, especially in view of his interest in destiny. It seems that the harsh circumstances that drove him to enlist early, at the age of sixteen, may have saved his life. When the Expedition was completed, his second enlistment period was due to end within six months. Therefore, in the midst of the raging World War I, he was not sent to Europe with the 27th Infantry. Later he learned that all of his friends from the Expedition had been killed.

When he re-enlisted for the third time late in 1917, he was assigned to the Quartermaster Corps, and was sent to Russia as a guard on the Trans-Siberian Railway. President Woodrow Wilson sent the expeditionary force to Siberia and the Russian Far East under the command of Major General William S. Graves for the purpose of protecting allied shipments carried by the railway. The great railroad had earlier been repaired by American railway men under Benjamin Oliver Johnson, who had been a superintendent of the Northern Pacific Railway. The American troops guarded only small sections of the railroad "from Mysovsk, on the eastern shore of Lake Baikal, to Verkhneudinsk and the section between Imam and Vladivostok." (See Trans-Siberian Railway in the World History, by Frederick C. Giffin, on the internet.)

After the war Raymond became a Disciplinary Barracks Guard, Pacific Branch, with a promotion to Corporal in June 1919, and was assigned to Alcatraz Prison. In 1853 the army had constructed a military fortress on Alcatraz Island and soldiers of the Civil War and Spanish-American War were confined there. Following the destruction of the San Francisco earthquake in 1906, Alcatraz received hundreds of civilian prisoners. The prison was at near-capacity by the 1920's.