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."