He (Roger) left Chicago for St. Paul, but he was unable to find work. Touhy describes his plight, "[I was] dead broke. I bummed my way out of the city aboard a freight train."
Eventually, Roger found work as a telegraph operator for various railroads and commercial houses as he made his way out west. During his travels he worked as an operator for the Union Pacific Railroad, then as a telegraph operator and later as a brakeman on the Northwestern Railroad. Finally he accepted a position as a telegrapher for $185 a month on the Denver & Rio and Grand Railroad and was sent out west by the company, often to Colorado, with most of his time spent in Eagle County.
It was here in Eagle where he befriended Clyde Nottingham, who was said to be the meanest cowboy in the region if not in the state. A giant of a man with a short temper, Nottingham grew up in the rough and tumble world of mining camps. He was a man beset with endless personal problems, and he acted as the local bully. 'When he wanted something," a relative noted, 'he just took it."
In 1899, Clyde married Tillie Samuelson. They had three children, a daughter Lola and twin sons, Harold and Clyde Jr. Harold, who was said to have been a bright child, died at age two, after a week's illness, and Clyde Jr. died in infancy.
Clyde had moved to the area from Iowa at the age of seven. Like his father, teamster William Henry Nottingham, he was known to be mean to the bone. Both men were known to threaten with death anyone that dared cross them.
In 1904, Clyde Nottingham beat and threatened to kill a depot agent named H.G. Comstock and then ordered him out of town. A few days later the clerk spotted Nottingham walking toward him, pulled out a revolver and fired three shots. Comstock failed to kill him but did manage to cut a hole through his pants and give him flesh wounds in two other places. A trial was held, but the jury, knowing Nottingham's reputation, acquitted the depot agent, who left town that same day. A while later Nottingham was arrested for beating up another depot agent-the one Roger Touhy replaced.
Several days after arriving in town Roger Touhy-the five-foot four-inch, ninety-eight-pound kid from Chicago's Valley who never backed down- met Nottingham, the giant rancher with the quick fists.
Roger remembered Nottingham: "I got my first warning of western bad-man danger when a local merchant told me, 'You won't be here long, sonny, we got a rancher, Clyde Nottingham, who runs depot agents out of town. He carries a gun. Guess he don't like you depot agent dudes.'"
He continues, "It was cold that first night in Eagle and I had the stove red hot as I jiggled the telegraph key, handling the freight car, stock car and personnel messages. The waiting room door opened and in came a big man in cowboy clothes and a sheepskin coat. He spat on the potbellied stove.
"I walked to the ticket window, looked out and saw the caller was carrying a .45. He didn't look pleasant, but damned if he was going to run me out of town. 'Mr.,' I asked. He nodded and I said 'Mr. Nottingham anytime you want to spit on the stove go right ahead. But come back the next day after the stove cools and polish it. I ain't going to do it.'"
Remarkably an agreement was reached. Touhy agreed to put Nottingham's letters on the late train and in turn, Nottingham agreed to stop spitting in Touhy's fire. This was the beginning of what Touhy would deem "a fine friendship." Touhy was invited to spend time at Nottingham's ranch with his family. Touhy admits this gave him a "sense of belonging," which he appreciated.
Spending his free time at Nottingham's three- hundred-acre ranch, complete with stream, lake and seven bedroom house, Roger learned big game hunting and horseback riding. He became a better-than- average marksman and acquired his life-long obsession with fishing.
Roger left Eagle after a two-year stay and in 1918 enlisted in the Navy and was eventually stationed at Harvard University where he worked as a wireless operator and taught officers the Morse code.
'The Navy," as Roger liked to point out, "gave grounds for me, a boy from the eighth grade to say honestly to cops, bootleggers, convicts, prison guards and interviewers, 'I've been to Harvard.'"
Opting for an early out with the Navy Reserve, Roger was back in Chicago by 1919, living with his father in suburban Franklin Park and dating Clara Morgan, having kept in touch with her through long letters from Colorado and later from Boston. There was talk of marriage, but Roger set off for the west again, landing in Drummund, Oklahoma where the oil business was in full boom and fortunes were being made overnight.
"I didn't know any more about the oil business then a mink knows about sex hygiene, but I could learn....The Sinclair Oil people, in a moment of laxity hired me as a scout. The experience I had in that line was confined to watching silent western movies in which army scouts killed Indians,"says Tuohy.
Actually the position he filled was as a driver to the world famous geologist Dick Raymond who had been brought in to determine which wildcat wells were producing the most oil and from that, decide which land was worth leasing. "There was nothing," he wrote "against my buying leases that Raymond recommended."
Learning everything he could about the oil business from Raymond, Roger took $1,000 out of his savings and purchased a 150-acre site that Drummond recommended. Within a month, he resold the lease for a 200 percent profit. He repeated the process twenty times in one year. Of that time Touhy said, "[I] never lost on any of them...the money was good, but I was a guy who liked the city. And my mind was on the girl at the telegraph key in the Blackstone Hotel."
He returned to Chicago with $25,000, a respectable fortune in 1920, "and,"he liked to point out, "it had taken me less than a year to earn it."