Raymond John Ryan (born January 9, 1904, in Watertown, Wisconsin) was a professional gambler, oilman, promoter, and developer. Described as having a larger-than-life personality, he mingled with prominent businesspeople and movie stars, as well as with card sharps and mobsters on his path to fame and fortune.
As a boy, he was fascinated with stories he read about Tarzan. He graduated high school in Watertown and then went to Northwestern. His father was a highway contractor.
In the 1920s he went into the oil business in Kansas but was unsuccessful. In the process, he did, however, learn some powerful lessons about making timely investment decisions.
Ryan lived in Milwaukee where he gained fame as a high stakes gambler while working a day job as a candy salesman. During his 8 years in Milwaukee, he met and married his wife, Helen Kelly. He was also alleged to help run a crap game and horse book at the corner of West Wisconsin and North 11th Street.
February 1935, Milwaukee register of deeds John W. Kelley (no relation to Helen Kelly) sued six gambling dens after his son lost $10,000 at them. Gamblers named in the lawsuits including Ray Ryan, Mickey Goldman, Louis Simon, Joseph Krasno, Sam Goldberg, Mac McLoughlin, Jack Lazarus, Hyman Finkelstein, Art Hoge, Murphy Klein, Harry Glinberg, Pete DeBroe, Joe Ickstedt, Abe Katz, Al Diamond, Harry Feinberg, Arnold Roe and Bob Duncan. Ryan was specifically identified with the Chateau Country Club (Highway 57) and the Manhattan Club (617 North Second Street).
Ryan finally succeeded in oil drilling in the 1940s due to the booming oilfields of southern Indiana, Illinois, and western Kentucky. His oil business was managed by Kentucky native, William “Billy” Gorman, who died in a mysterious horse-riding accident in 1974.
December 1941: Ray Ryan and his wife were staying at a downtown Chicago hotel. Two men entered their suite, tied them up and left them in the bathroom. The intruders escaped with $7,400.
At some point, was a New York franchise holder in the All-America Football Conference with Mrs. Lou Gehrig. Conference head Arch Ward asked him to sell his interests because he was a known gambler. This league only existed 1946-1949, so it would be in there. When it folded, the San Francisco 49ers and Cleveland Browns joined the NFL.
In 1949, Ryan gave an inscribed gold key chain to Las Vegas mobster Davie Berman that read, “DB from Ray Ryan, 1949.”
Also in 1949, Ryan played a high stakes game of “low ball” poker with Nicholas “Nick the Greek” Dandolos and won $550,000 from Nick. The game went on for 15 or 16 sessions over a few weeks alongside the pool at the Flamingo Hotel in Las Vegas. James Harakas, a lawyer and government official in the Interior Department, personally brought $323,000 of Nick’s money to Ryan over four different days. (Friends of Ryan’s would later claim he also once won $800,000 at a game in Florida, and bet $200,000 on a single football game.)
In 1951, Ryan was at the Horseshoe Club in Las Vegas with Dandolos, Harakas and a man named Steve Pappas. Dandolos accused Ryan of cheating in that earlier game and demanded $195,000 back. Ryan denied it, but offered to pay $135,000 to avoid embarrassment of being called a cheater.
June 1951, Ryan was actively pursuing an oil deal in Zubair, Iraq. Not sure if it went through.
In the 1950s and ’60s, Ryan was a land developer in Palm Springs, California. Real estate development in Palm Springs did not generate much interest until actor Clark Gable built a home there. Ryan joined with 24 other investors to purchase the run-down El Mirador Hotel in Palm Springs. After restoring it to its former elegance, he bought out his partners in 1960 and then sold it. The list of regular guests included William Holden, Dean Martin, Gregory Peck, Paulette Goddard, Ginger Rogers, Louella Parsons, and Freeman Gosden, among others. Howard Hughes secured a separate cottage to ensure privacy.
In 1962 Ryan, with partner Ernie Dunlevie, opened the Bermuda Dunes Country Club which later became a host club for the Bob Hope Classic golf tournament and where Clark Gable built a home on the sixth fairway. Bob Hope joked the golf course was so far out in the desert that caddies had to be recruited from the foreign legion.
July 5, 1963: Marshall Caifano, Charles DelMonico and Allen Smiley (real name Aaron Smehoff) were arrested for a $60,000 “shakedown” of Ryan. Ryan alleged the men met him at the El Mirador in Palm Springs on April 26 and demanded he pay them the money he owed Nick the Greek. Ryan refused, and shortly (May 1) after they busted into his hotel room in Las Vegas and made the demand again.
January 16, 1964: The extortion trial started. Ryan testified that the men told him that he had to pay and had no protection from them. “I know you know a lot of people, including Bobby Kennedy, but we’ll take care of that, too,” Caifano allegedly said. Ryan said he ran from them and yelled back, “Shoot me in the back. That’s the way you do business.”
January 24, 1964: Extortion charges were dismissed against Allen Smiley by Judge Jesse Curtis. The judge said, “There is no direct testimony or evidence of Mr. Smiley’s participation in any one of the alleged offenses.”
February 5, 1964: Defense attorney James Hogan said Ryan was “a liar and a card cheat and unbelievable on the witness stand… When Ryan found out Dandolos was going to sue him and he would be exposed as a cheat, the extortion plot was hatched in his mind.”
On February 7, 1964, Marshall Caifano and Charles DelMonico were convicted of extorting $60,000 “protection money” from Ryan, who testified against them. On March 31, Caifano was sentenced to 10 years and DeMonico to 5 by Judge Jesse Curtis.
The conviction was upheld in 1966, and they began their sentences. When Caifano was released from prison in the 1970s, Ryan reportedly offered him $1 million in restitution.
December 16, 1968: Ryan was indicted in Los Angeles on charges of conspiracy and obstruction of justice. US Attorney Matt Byrne said Ryan had “manipulated” records of the Mount Kenya Safari Club previously subpoenaed during a 1967 investigation into racketeering. The conspiracy charge came from his working with secretary Helen Hansen to alter the records. Specifically, records were destroyed or changed to hide the financial involvement of New York gambler Frank Erickson, who was allegedly setting Mafia members up with memberships. Other members included Winston Churchill, Bobo Rockefeller and Dr. Norman Vincent Peale, though there’s no evidence these three ever actually went there.
Ryan was convicted and sentenced to three years in prison on September 14, 1970. The conviction was reversed in December 1971 by the court of appeals.
Ryan was the target of an IRS audit in the 1970s over some disallowed deductions stemming from his involvement in and development of the Mount Kenya Safari Club, in Nanyuki, Kenya, with actor William Holden and Swiss banker Carl Hirschmann.
On October 18, 1977, Ryan went to a health club in Evansville, Indiana, as he often did. When he finished his workout, he walked outside to his new Lincoln Mark V coupe. However, someone had connected a dynamite bomb to the ignition of the car. As soon as Ryan turned the key, Ryan’s car exploded violently. The impact of explosion killed Ryan almost instantly. It took investigators two days to locate and collect all of the pieces of the car – one piece of metal was located 377 feet from the scene of the explosion. The bomb damaged nearby cars and took out power in eastern Evansville. The murder is unsolved.
Marshall Caifano was an obvious suspect. Another suspect was Nick the Greek, though Nick was dead – did someone else get revenge on Ryan for Nick from the grave?