Ray Ryan - Life as a Gamble
By Herb Marynell
Evansville Courier & Press, October 14-18, 2002
Oil and gambling do mix, and Ray Ryan excelled at both. Gambling and oil suffered little during the Depression, and they brought money - and colorful characters - to Evansville. Prohibition during the 1920s made some of those who supplied illegal liquor wealthy. It also sped the creation of organized crime in major cities. When Prohibition ended on April 7, 1933, those with money looked for other ways to make more, and gambling and bookmaking came to the forefront. Big gambling areas were New York, New Jersey, Chicago, New Orleans, Florida and Hot Springs, Ark. But, Evansville did more than its share. Gambling already was in the blood of oil men. And hundreds of them poured into Evansville in the late 1930s, trudging fields during the day, ending up in hotels at night, muddy from a day’s work and ready to trade yarns, information and oil leases. Officials at the Vendome Hotel didn’t take kindly to dirty carpets and the mess. Soon, the McCurdy Hotel, where officials had less discerning tastes, became the headquarters for many oil men who spent idle time gambling. Ron Lankford, retired Old National Bank president who started working at the bank in 1956, said the oil men would send the hotel bell captain over before the bank closed at 2 p.m. with checks for $500 or $1000, whatever they felt they needed for a night of gambling... Ray Ryan, Lankford recalled, would come into the bank occasionally to pick up $10,000 for “walking around” money. A Ryan friend also remembered Ryan going swimming in the Bahamas with $5000 in a swimsuit pocket. Even in the late 1930s, city officials sought to halt the city’s growing gambling element. In 1938, Mayor William Dress ordered a ban on slot machines in public places. Police arrested bookies, and citizen groups urged a greater crackdown on gambling. In May 1939, 48 bookies operated in Evansville, paying $35 a month for the telegraph service bringing in race results. Dress eventually said the lid on gambling would be put on “perpetually, everlastingly, forever and longer than that if possible.” Little did he and the citizens groups realize the futility of it all. Evansville was on the verge of one of the most amazing periods in its history. The Trocadero Club opened in the fall of 1939 on “no-man’s land” along U.S. 41 South north of the Ohio River on property in Kentucky. The club offered plush surroundings, top entertainment and an upscale gambling operation upstairs. Other gambling clubs, often joints catering to the less wealthy, opened in Evansville. When the United States became involved in World War II, thousands of military personnel from bases in Kentucky and other cities would come to Evansville where nightclubs, gambling, red light districts and other activities flourished. Noted gambling expert John Scarne concluded that in the 1940s, “Evansville, Ind., had more horse rooms and gambling dives per capita than any other city in America.”
There wasn’t a lack of tips, clues and ideas on why Ray Ryan was killed in a car bombing on Tuesday, Oct. 18, 1977. The problem for federal, state and Evansville investigators, though, was figuring out which tips meant anything. Information rolled in as dozens of police officers scoured neighborhoods, businesses and hotels. Altogether, 40 local officers were involved in the early investigation. Witness reports included: A white and blue car, possibly a newer model Ford, parked on the street with a man inside reading a newspaper. It was parked behind Ryan’s Mark V. A man running just before the explosion to a dark blue Lincoln or Cadillac with Kentucky plates parked near the Olympia Health and Beauty Resort, where the bombing occurred. A “rough-looking” man in the city prior to the bombing, tipping waitresses $50 and $100 and driving a car with Delaware plates. A man, who looked like Elvis Presley only much larger, talking at the Executive Inn on Monday saying “something big” was going down Tuesday. The man drove a black Cadillac with a white top and Texas plates. A cream-colored Chrysler Cordova, with Pennsylvania plates, operated by a man, about 35, dark-skinned, Italian looking. It, too, was parked near the spa. Neighbors near Ryan’s residence reported seeing several different cars parked on the street in days and weeks before the bombing, apparently watching the Ryan home. One car with two men drove off when a neighbor walking his dog approached. Another car was occupied by a man about 50, stocky, wearing a gray felt hat. Police ran down those tips and dozens of others, but no definite leads resulted. Officers fanned out to the city’s hotels and motels, collecting the names of those registered there three days prior to the bombing. The list was up to 1000 people. Records from car rental companies were obtained. The numbers of telephones at restaurants and phone booths were taken down, and calls were painstakingly checked. An examination of Ryans’ Mark V showed it was in park with the ignition on at the time of the explosion. Employees from the local Lincoln dealer said there were only a few places to attach a bomb under that car, and police theorized the bombers were pros. Attaching a bomb to the car, police concluded, would take less than two minutes. David Newcomb, the spa manager that day, still wonders about the man sitting in a nearby car reading a newspaper, and whether someone triggered the explosion with a remote control. The car was across the street in the auto parts store parking lot facing the spa. As he came to work Oct. 18, Newcomb saw the car, thinking it unusual someone would park there. The store was closed the day before the bombing and remained closed on Tuesday, Oct. 18, 1977. When Ryan arrived at the spa, he handed Newcomb, who was at the counter, his gold necklace with gold coins and a medallion for safe keeping. Ryan usually worked out about 20 minutes on light weights before swimming in the spa’s pool, and he didn’t wear the necklace when swimming. Newcomb placed it in a lockbox. Newcomb’s dad, Kenneth Newcomb Sr., the owner, was in the spa that day. He said he talked about 15 minutes with Ryan, and he planned to go with him later and look at real estate Newcomb had purchased. But Newcomb said he first had to go home on an errand, and he had driven four blocks when he heard the explosion. David Newcomb said he was taking the trash out when the blast occurred, knocking him to the ground. The younger Newcomb raced outside, fearing his father, who had just left the spa, was hurt. Newcomb looked at the body on the parking lot asphalt and knew it was Ryan. He saw the necklace.
About 30 people attended the private funeral for Ray Ryan on Oct. 20 at Ziemer’s Fountain Terrace East funeral home. And undercover police and FBI agents were around, one investigator posing as a window washer at a nearby business so he could take pictures of people who attended the funeral. Actor William Holden, Ryan’s longtime friend and a partner in the Mount Kenya Safari Club in Africa, was there. Holden left the funeral with Lt Gene Martin and police officer Steve Bagbey to talk. The 59-year-old Holden said he was introduced to Ryan in New York City in 1939 by Lex Thompson, then owner of the Philadelphia Eagles National Football League team. Holden said he met Ryan again during World War II at the El Mirador, the Palm Springs, Calif., hotel that Ryan and a group of investors restored, helping enhance Palm Springs standing as a playground to movie stars. Holden told the investigators that he joined Ryan in oil ventures in Kentucky in 1953 that resulted in 13 dry holes. Holden said he jokingly told Ryan he would stay out of the oil business if Ryan, whose attempt to buy RKO Pictures failed in 1952, would stay out of making movies. He met with Ryan in 1958 in Europe for a safari that resulted in them agreeing to go into business together and buy the safari club, Holden said. Ryan eventually sold his interest in the club. Ryan’s daughter, Rae Jean, said her father was dear, kind and loving. Also interviewed was Frank Hayden, who watched over Ryan’s businesses in California, and Doyle Dressback, who handled the local oil company operation and Ryan’s Lake Malone Inn in Kentucky. The person who had handled Ryan’s business operations for years, William Gorman, died in 1974 in a horseback riding accident. Ryan, police learned, usually divided his time among Africa, Palm Springs, Lake Malone and Evansville. Steve Bagbey today is 54, and an Evansville City Council member for the past 11 years, representing the city’s 2nd Ward. In 1977, he was working in the bunco-fraud unit of the police department. By January 1978, the investigation into Ryan’s murder seemed at a standstill. Bagbey said Lt. Frank Gulledge of the detective department told him to devote all his attention to the Ryan case. Bagbey said he was surprised by the assignment, since other detectives had more experience. He later was told he was selected because they “wanted someone who would push and not take no for an answer.” Today, federal or local investigators in the Ryan case still refer most questions to “Bags,” Bagbey’s nickname, because the Ryan case never left Bagbey.
The Ryan murder case took dizzy turns in 1978. Investigators looked into former police officers with the Lexington, Ky., police department, who left the agency and ran into trouble with the law. One of the men, while still an officer, met Ryan and other friends during a visit to a Lexington hotel, and tried to sell paintings by Glen Robinson. Ryan liked that painter, took him to Africa once and provided him a studio at Lake Malone. Local witnesses viewed mug shots of the former Lexington officers, but that lead didn’t pan out. A former Evansville police officer who was in state prison said Puerto Rican terrorists had bombed Ryan. Time was spent visiting northern Indiana and Chicago to check into the terrorist group. Witnesses were re-interviewed, evidence checked. Contacts were made with police agencies in states where Ryan had enterprises - California, Texas, and elsewhere. Deeper contacts were made with the FBI, ATF and federal Strike Force groups across the country. Interpol was asked to interview Ryan’s acquaintances in Europe. Although all agencies wanted to solve the murder, Bagbey would discover FBI and ATF offices sometimes engaged in “turf wars” during the investigation. He would become frustrated with the bickering among federal agencies.
A year after the bombing, federal agencies had spent more than $100,000 in the investigation. Bagbey interviewed singer Patti Paige, the former wife of Charles O’Curran, a longtime friend of Ryan. Ryan was the best man at Paige’s 1956 marriage to O’Curran, a choreographer for movies, including ones by Elvis Presley. Paige and O’Curran divorced in 1972 and Paige hadn’t seen Ryan since then. The Ryans, she said, were gracious to her. She recalled O’Curran once saying Ryan had a suitcase full of money in a New York hotel. She also said a man passing through stayed briefly at their Beverly Hills, Calif., home. O’Curran later told her the man was Sam “MoMo” Giancana, then a suspected member of the Chicago mob. O’Curran, police would learn, would travel to Palm Springs, Evansville or other places to visit Ryan and play cards. O’Curran fell out of favor with the Ryan family after Ryan’s death. About two years after Ryan’s murder, the U.S. Attorney’s office in Indianapolis called a grand jury to hear testimony about Ryan’s slaying. The grand jury was called to make sure witnesses would cooperate and to give authorities an idea where the case stood, Bagbey said. The grand jury testimony could become a permanent record of testimony if witnesses died before an arrest, he said.
Mob-ordered killings were common in Chicago during the first half of the 20th century. The Chicago Crime Commission logged 986 gang killings between 1919 and 1964. Of those, 727 were committed between the years 1919 and 1934. In all, just 13 of the 986 cases resulted in murder convictions. Killings increased after Al Capone came to Chicago in 1919 to join his New York boss Johnny Torrio to take over one mob and battle other gangs for control of saloons, gambling joints and houses of prostitution. With the arrival of Prohibition in 1920, the wars escalated. Millions were to be made by offering illegal liquor. By the close of the 1920s, Capone ruled Chicago. He beefed up his forces by recruiting young toughs from the “42 Gang” and the “Circus Gang” on Chicago’s west side, gangs that quickly went from auto theft and burglary to murder and mayhem. Several became top figures in Chicago’s organized crime, and some figured prominently in the life of Ray Ryan. The “42 Gang” members included Sam Giancana, Sam Battaglia, Felix “Milwaukee Phil” Alderisio, Albert “Obie” Frabotta, Charles Nicoletti and Marshall Caifano. Most were investigated in more than a dozen murders each. Alderisio and Nicoletti were the mob’s main executioners, police said. The “Circus Gang” contributed Tony Accardo, Tony Spilotro, Joseph Hansen and others. Accardo later had one of the longest and most efficient reigns as head of the Chicago syndicate. Giancana, Battaglia and Alderisio also would become mob bosses. They would have parts in Ray Ryan’s life, but Caifano, who never reached the pinnacle of the Chicago mob, had a lead role. Born July 19, 1911, in New York City, Caifano moved to Chicago as a youth. At 5-feet 5-inches in height, Caifano was known as “Shoes” for using elevator shoes. Between 1929 and 1951, he was arrested 18 times, often under other names, for auto theft, grand larceny and other crimes. The Chicago Crime Commission in 1958 said the tough, stocky Caifano was questioned numerous times about gangland murders and shootings. Among the cases were slayings of other hoodlums, another’s girlfriend who was bludgeoned and burned to death, and a man who killed Caifano’s brother. But Caifano’s career was on the rise. In the 1940s, wide-open gambling parlors and casinos in Florida were closing under pressure from local and state officials.
Organized crime was looking for better places to make money. That became Nevada, which legalized all forms of gambling in 1931. Reno already had casinos, but the spotlight soon shifted to Las Vegas. In 1946, Benjamin “Bugsy” Siegel, backed by New York mobsters Frank Costello and Meyer Lansky, opened the Flamingo in Las Vegas. The love affair between organized crime and Las Vegas bloomed. But the mob’s love of Siegel did not. Siegel, believed to have pocketed large sums of construction money, was killed in 1947. During the decade after the Flamingo’s opening, more New York-backed casinos opened, providing millions to be skimmed. Chicago didn’t get a Vegas casino until the Stardust opened in 1958. John Drew, a familiar face in Chicago, represented the Chicago syndicate in the Stardust’s operation. He came from the Bank Club casino in Reno, which the Chicago mob took over a few years earlier. Drew’s name would show up frequently as a friend of Ray Ryan. Caifano was calling Las Vegas a second home by the early 1950s. He was sent there to buy property and take care of problems for his bosses. While in Nevada in 1955, he legally changed his name to John Marshall. Also often showing up with Caifano was Charles Delmonico, who had changed his name in 1953. Delmonico was born Charles Tourine Jr., the son of one of the New York Genovese family’s top members, Charles Tourine Sr., a key figure in the family’s drug and gambling operations. A crack in organized crime’s influence in Las Vegas occurred in 1957 with the shooting and wounding of Costello in New York. Police found a note listing the day’s take at the Vegas Tropicana casino in Costello’s pocket. Media coverage focused on organized crime and Las Vegas, and reforms would slowly occur. Also in 1957, Accardo stepped down as Chicago’s mob boss after a term that began in 1946. As his replacement, he selected Giancana, who assigned Caifano to be Chicago’s representative in Las Vegas. Police said Caifano used intimidation - and possibly more drastic measures - to assert his authority. Gus Greenbaum, who turned struggling casinos into a large profit for syndicate owners, was a problem in 1958 because of drugs, drinking and huge gambling losses. In December, after Caifano took over his new job, Greenbaum and his wife were found dead in their Las Vegas home, their throats slit. No one was ever charged. In 1960, Nevada started the Black Book of undesirables, people banned from the casinos. Caifano was among 11 on the first list. He kept going into casinos and state officials had him arrested. Caifano filed a lawsuit to remove his name from the Black Book, but he lost in court. By 1963, Caifano was on a downhill slide. He and Delmonico would soon encounter extortion involving Ray Ryan and end up in jail.
Ray Ryan sat outside a Las Vegas casino at a table of cards, facing one of the world’s most famous gamblers. It was 1949, and the Thunderbird Casino was among the newest clubs on the expanding Las Vegas strip. Ryan, a 45-year-old millionaire oilman, was pitted in a private game of lowball poker with Nicholas “Nick the Greek” Dandolos, legendary for his skills at the card table. Both were accustomed to card games with stakes worth six figures. Ryan, a friend said, would train for weeks for games of such importance. He had a knack at cards, being able, for example, to determine a player’s hand after a few draws and discards in gin rummy. The game with Dandolos lasted a week or more, lasting five and six hours a day. It ended with the 67-year-old Dandolos losing $550,000 and reportedly paying a large portion, or all, of the loss. Dandolos later claimed he learned from a man that Ryan had cheated. The allegation: The man said Ryan paid $20,000 to use confederates to monitor the game with binoculars. Ryan would then learn about his competitor’s hand through a short-wave device.
Dandolos said he demanded the money back in 1951, but received only $26,000. Ryan denied cheating and playing in that 1949 game. He did say, however, that he won $15,000 from Dandolos in a 1951 game at the Flamingo casino. The story of the Ryan-Dandolos game, however, made the rounds. Novelist Ian Fleming used the scenario in his 1959 James Bond book, and subsequent movie “Goldfinger.” The incident, investigators would later believe, also set off a chain of events that would lead to Ryan’s 1977 car bombing death.
Ryan was a familiar figure in the 1950s in Las Vegas, where he was known as a high roller who often bet against house odds. Those in Palm Springs also knew him as a developer of houses and clubs. Around 1952, Ryan and 17 investors purchased the El Mirador Hotel in Palm Springs and spent nearly $5 million to restore the hotel to its former glory. Built in 1928, the hotel had declined after World War II, when General Patton used the property for troop training. Ryan bought out the other investors in 1960, but sold the hotel before the decade’s end. Ryan also acquired vast tracts of land around Palm Springs and began developments in the 1950s. He built a home that he gave to Clark Gable in hopes of attracting other movie stars to buy second homes in Palm Springs. Frank Bogart, Palm Springs mayor during the 1950s, called Ryan “one of the greatest guys who ever lived. He was the best liked guy we ever had here. “You couldn’t find a nicer guy, happy, laughing, and giggling. He was doing something every minute,” said the 92-year-old former mayor, who lives in a subdivision developed by Ryan. Ryan would be known as “Mr. Palm Springs,” he said, and was the “desert’s greatest booster.” Ryan knew a lot of movie stars, and they came to Palm Springs, Bogart said. “All the important people came here - the queen of England, Prince Philip.” So did President Eisenhower, and Ryan was there to greet him. President Kennedy visited four times, and his brothers made visits, as did Vice President Gerald Ford. Bogart said Ryan was a “one-man chamber of commerce for the city.” At one time, Ryan was the largest single developer, building the Bermuda Dunes Country Club and surrounding area with Realtor Ernie Dunlevie. Ryan owned a good portion of downtown Palm Springs. He also owned 2500 acres in nearby Desert Hot Springs. Ryan and Don Eastvold spent millions developing the North Shore Beach Yacht Club and Marina with a capacity for 400 boats, a luxury hotel and homes at Salton Sea, 30 miles south of Palm Springs. Ryan, Dunlevie and Charlie Farrell, a former silent screen actor, were building the new Bermuda Dunes Racquet Club when Ryan was killed. Farrell called Ryan “a wonderful guy, very sweet and nice and a gentleman at all times.” Bogart said Ryan made $10,000 a day from his oil holdings. So he made numerous donations to local charities and programs, but also frequently visited Las Vegas to gamble. “I had gamblers in Vegas tell me he was the best gambler ever,” Bogart said. “He could remember every card.” Bogart said Ryan’s only association with organized crime figures was playing poker with them. “They were the only guys who had money. He (Ryan) had to have someone rich enough to make it interesting for him,” Bogart said.
While people in Palm Springs watched Ryan with admiration, others in Las Vegas watched with greed. Marshall Caifano had been the Chicago mob’s representative for a few years, overseeing any problems. His friend, Charles Delmonico, was considered a “roving ambassador” for Chicago out west. The Nevada Gaming Commission banned Caifano from the casinos, putting him on the first Black Book in 1960.
In 1963, Caifano and Delmonico - well aware of Dandolos’ claim of Ryan’s cheating - decided to extort $60,000 a year from Ryan, supposedly to repay Dandolos, according to court records. Caifano’s fellow mobster, Felix “Milwaukee Phil” Alderisio was being investigated at the same time for three cases of extortion, one in Florida and two in Colorado, according to reports. Mob informants told investigators extortion was a way to obtain “walking around money.” Ryan reported the extortion attempt to the FBI. “They tried it once before. It didn’t work then and it never will work. They won’t get anything out of me,” Ryan told a Chicago newspaper. Ryan said he was the object of shakedowns in the past, “but I didn’t pay off and I never will.” Federal authorities charged Caifano, Delmonico and Allen Smiley, who later was acquitted, in the Ryan extortion case. The 1964 trial was held in a Los Angeles federal court. Ryan was kept under FBI protection until the trial, and he hired a bodyguard. The extortion attempt, according to news reports of the trial, started when Caifano contacted Ryan at the El Mirador Hotel in April 1963. Ryan said he talked with his old friend, John Drew, co-owner of the Stardust casino and long associated with the Chicago mob’s gambling operations. Drew told Ryan that Caifano was “OK.” When Caifano and Delmonico arrived at the hotel in a car on April 30, Ryan got in. Delmonico was driving, and Caifano was in the back seat. Ryan, still unsure of the two men, told the hotel bell captain and a hotel stewardess to follow in another car. During the car ride, Ryan testified, Caifano and Delmonico mentioned the Vegas card game with Dandolos. They demanded $60,000 a year as syndicate protection money and $15,000 to repay Dandolos. Delmonico, Ryan testified, struck him across the chest, saying “that’s just to show you we mean business.” The argument over money continued until Ryan was let out of the car because he was flying to the Desert Inn in Las Vegas that night. Ryan said he had someone contact Drew, then in Reno, who said there was nothing he could do. At noon on May 1, Caifano came to Ryan’s room at the Desert Inn, saying Ryan hadn’t paid. Caifano said the syndicate had protected him in the past from being kidnapped, but from now on he had to pay $60,000 a year, Ryan testified. Ryan quoted Caifano as saying: “You’re one of the people we’re going to put in line. I know you know a lot of important people, including Bobby Kennedy, but we’ll take care of that too.” Caifano said they were going for a “little ride in the desert.” Ryan testified he was escorted out into the hallway, where he saw Delmonico and Dandolos. He then made his getaway, dashing behind a a porter and his luggage racks. He started running, saying: “Shoot me in the back - that’s the way you do business.” Ryan told the court “I thought I’d make my stand. If I was going to get it, it would be right now. I wasn’t going in that car into the desert.” Ryan would say several Chicago crime figures tried to convince him not to testify, including John Roselli, the man Caifano replaced as Chicago Las Vegas representative, and Sam Giancana. They warned he would have trouble with the IRS if he testified. (Ryan did face problem with the IRS after the trial.) Ryan’s friends and an informant later told police a prime reason Ryan went to the FBI was because of being struck by Delmonico. The Los Angeles extortion also resulted in Delmonico being charged for an Evansville bank robbery. When his picture appeared in Evansville papers in 1963, employees of the First Federal Savings bank said Delmonico was the man who robbed them on Oct. 8, 1962, of $22,800, then the largest bank robbery in the city’s history. John Stinson, the bank’s executive vice president, said the robber forced him to open the vault, then drive the robber away. After four blocks, the robber told him to stop the car and walk back to the bank, Stinson said. I
n 1965, the charges were dropped after Delmonico’s noted Washington, D.C., attorney, Edward Bennett Williams, and federal authorities said Delmonico, who said he was in Florida when the robbery occurred, passed a number of lie detector and truth serum tests. The bank vice president and teller, however, continued to claim Delmonico was the robber. J. Robert Duvall, a retired FBI agent, said he believes Delmonico was in Evansville in 1962, tracking Ryan. When he discovered Ryan was out of town, he decided to rob the bank instead, he said. During the 1964 Los Angeles trial, Dandolos filed a civil lawsuit against Ryan, seeking $1.5 million in damages. The case later was tossed out and Dandolos died shortly thereafter. Marshall Caifano’s problems didn’t end with his extortion conviction. He had fraud and other charges to face. Caifano received a 10-year sentence, and Delmonico a five-year sentence, in the Ryan case. Both eventually went to federal prisons in 1966. Delmonico was released in January 1970 and Caifano in December 1972. But Caifano never forgot Ray Ryan. His hatred of Ryan, authorities would learn, would eat at Caifano for years, even after he was free.
In 1957, Ray Ryan had entertained top political leaders, made millions in oil and entrenched himself as a man of respect among Hollywood stars, sports heroes and society’s elite. By the end of that year, though, Ryan would also attract attention from a new group: investigators with the federal government. Two events in November of 1957 focused the government’s attention on organized crime, and that meant Ryan, too, became entangled in the dragnet. On November 14, police broke up a meeting of the country’s major organized crime bosses gathering at Apalachin, a small community in upstate New York. The resulting publicity forced FBI Director J. Edgar Hoover to crack down on organized crime. Soon all federal agencies focused on anything resembling organized crime. About two weeks after that raid, federal agents broke up a Terre Haute, Ind., gambling operation that handled as much as $10 million in bets during a 10-week period. A federal grand jury was convened to investigate the gambling operation. More than 170 people nationwide were subpoenaed, and Ryan was one of them. The investigation uncovered a nationwide telephone betting system that had wagers on everything from college and professional football to the World Series. Bets on single games were as high as $10,000. Records showed numerous telephone calls between Ryan and the gambling operation, federal officials said. In 1958, Ryan went to Europe to avoid attempts to subpoena him. Ryan was in Belgium when federal officials got legal proceedings completed to subpoena him there. Before he was served with the subpoena, however, he moved to Switzerland and the whole process had to start over. Before that could be done, the federal grand jury’s investigation was over. But Ryan’s troubles with the federal government were just beginning. While federal officials became interested in Ryan in 1957, other law enforcement agencies noticed Ryan earlier. He was a frequent visitor to Chicago. Chicago newspapers would note Ryan would be seen at high-stakes card games in the Blackstone Hotel. In 1941, Ryan and his wife, Helen, were robbed by two men who posed as FBI agents. They stole $7400 in cash and jewelry, newspapers reported. Helen Ryan reportedly told her husband it was a holdup. Ryan opened an eye and said: “It’s just a gag. Tell them to quit kidding.” The two men, one an escapee from a Texas prison, were captured the following year and convicted. In 1953, FBI agents arrested the sheriff of Madison County, Texas, for aiding in the escape of prisoners, including one who robbed the Ryans. That announcement was made by J. Edgar Hoover. In 1944,
The New York District Attorney’s office asked the Chicago Crime Commission for information about Ryan. And in 1951, the Pinkerton Detective Agency sought information on Ryan’s involvement with New York gangster Frank Costello after Costello’s testimony before the Kefauver Senate investigating committee. Letters were exchanged in 1953 between the Chicago Crime Commission and officials in Nevada, where John Drew was seeking a gaming license. Drew, said Chicago officials, was a close friend of Ryan and staying at Ryan’s El Mirador Hotel in Palm Springs. Drew, once a dealer and employee in Chicago clubs, was arrested in 1943 on gambling charges. One memo by Chicago officials said a confidential informant told of a plan by Drew and friends to take a large sum of money from Jack Benny in a crooked dice gambling game. There was no indication such a game took place.
In 1958, actor William Holden received a call from Ryan, still in Europe, inviting Holden to join him for an Africa safari. In Africa, Ryan and Holden stopped at a hotel where Ryan complained about the service. Holden asked Ryan why he didn’t buy the hotel and make things right. Ryan did the next day. Ryan, Holden and Carl Hirschmann, head of the Commercial Credit Bank of Zurich, became partners in acquiring the Mawingo Hotel in Nanyuki, Kenya. They turned the hotel and grounds into the Mount Kenya Safari Club, an exclusive playground for the rich and famous that still exists today. Ryan figured club visitors would want to hear tom-toms at night so he built a nearby village for 200 who played tom-toms. The safari club was a hit, and Ryan also built schools and clinics and other facilities for the area. Charter members of the safari club included Winston Churchill, former President Eisenhower, Prince Bernhard of The Netherlands, Henry Ford, Walt Disney and Hollywood stars like Clark Gable, John Wayne and Joan Crawford. Evansville’s mayor, Frank McDonald Sr., was also a charter member. There were other names on the list, however, that would later interest federal investigators. Frank Erickson, king of the bookmakers and a friend of Ryan’s, gave memberships to 18 people at the top of the New York mob in the early ‘60s. The names including Gerardo Catena, Thomas Eboli and Pasquale Eboli. When Ryan testified in a 1964 federal court case in Los Angeles against two Chicago mobsters who tried to extort $60,000 a year from him, the IRS was on alert. Court documents showed an IRS agent began investigating Ryan in 1964 because of testimony in the extortion trial about Ryan gambling with large stakes. In 1969, the IRS filed a U.S. Tax Court civil suit claiming Ryan owned $6.7 million in taxes and penalties for alleged unpaid taxes from 1958 to 1965. The government slapped $9 million in tax liens on 50 Ryan properties in nine state. Federal officials said they suspected Ryan was laundering his own income and possibly organized crime cash through a Swiss bank. A long court battle ensued as the government sought Swiss bank records and records from Ryan’s companies in Kenya. The Justice Department also filed a criminal case, saying Ryan altered the records of the Mount Kenya Safari Club to conceal the membership of top organized criminals. Ryan was convicted in July 1970 in federal court and sentenced to three years in prison. An appeals court, though, reversed the conviction. Herbert J. Miller Jr., Ryan’s attorney, said Ryan only meant to protect charter members, not obstruct justice. Miller, now 78 and still practicing law in Washington, D.C., was assistant attorney general in charge of the criminal division - a presidential appointment - during Ryan’s 1964 testimony against mob figures in Los Angeles.
Miller went into private practice in 1965 and was eager to represent Ryan in the Mount Kenya membership criminal case. “I went to bat for him because he had testified for the government (in 1964) and put himself at risk,” Miller said. Miller doesn’t believe Ryan laundered any money. “As far as I was concerned he was not guilty of any crime,” Miller said. “They (the IRS) were sure after him,” Miller said. Miller said he asked federal officials several times for proof Ryan was tied into organized crime. “I never got a straight answer or an answer I could believe,” Miller said. “I hate to think how much they spent on the investigation.” Ryan’s high-stakes gambling would cease during the last 10 to 15 years of his life, police investigating Ryan’s 1977 murder were told. Ryan still played cards - gin rummy, poker, Spite and Malice - as much as possible, but the days as a high roller were over, police were told. Years before his murder, Ryan told a reporter: “Every time I made a bet it would be exaggerated four or five times as the story went around. When it got to the government, it was a staggering figure. “It got so every time I wanted a little action, two months later I had to spend three days with the men from the IRS. So now I don’t bet at all or I wouldn’t have time to take care of my business.” The government would get $2.5 million from Ryan’s estate to settle the tax court case. Ryan’s estate was $12 million. Ryan would sell the safari club, but would return to Africa for months at a time to visit. To get IRS permission to travel outside the country, Ryan had to put some of his Indian Wells holdings as bond. “I never seem to have time to think until I get to Mount Kenya,” Ryan once told a reporter. “It’s the only time where I feel like I can take a deep breath. When I die I want to be buried there.” After he died in the 1977 car bombing, Ryan was cremated and his ashes were taken to Africa by his wife, Helen, who died in 1998. She once told an Evansville newspaper executive that “Ray’s never happy unless he is walking on the edge.”
A road map for investigators into the 1977 car bombing slaying of Ray Ryan came from unlikely sources - federal informants. Investigators learned key information from four of them. They learned that Ryan’s name had been used as bait in the mob-ordered executions of two hoodlums. They learned of the deep-seated hatred of a mobster who wanted to see Ryan slain. And one informant gave information about two mob enforcers who triggered the bomb that killed Ryan 25 years ago today. Three informants would tell investigators about Marshall Caifano. Caifano spent six years in federal prison because Ryan testified in 1964 against him and Charles Delmonico, two men Ryan claimed had tried to extort $60,000 a year from him. One federal informant said Delmonico struck Ryan during the extortion demand. Ryan was so angry about being hit that he decided to testify, ignoring requests from other mob figures to remain quiet. Ryan’s decision to testify, an informant would say, was a way to protect his pride, more important to him than his own life. When Caifano got out of prison in December of 1972, he was 61 and no longer a force in the Chicago mob He received menial chores such as watching over porn shops. His mentor, Sam Giancana, was gone as Chicago boss, stepping down after a year in prison in the mid-1960s for refusing to testify before a federal grand jury under immunity. Two other old Caifano mates, who had served a year or two each as Chicago’s mob boss after Giancana left, were in jail. Joseph Aiuppa was the Chicago boss when Caifano got out of jail, and Caifano would try to work his way up in the Chicago crime hierarchy. It was a November 1977 telephone call by Caifano that helped push one of the informants, Aladena “Jimmy the Weasel” Fratianno, into the federal witness protection program in 1978.
Police said Fratianno probably committed 16 murders, helped plan others and served for a time as mob boss in Los Angeles. He would become the FBI’s most important informant. According to a 1981 biography of Fratianno’s life, Caifano called Fratianno in 1977, asking him to come to Chicago to introduce another individual to Benny Binion, owner of the Horseshoe casino in Las Vegas. Fratianno knew that Caifano knew Binion as well as anyone, and that the Chicago and Los Angeles syndicates were then in conflict. Fratianno concluded he was being set up to be killed if he went to Chicago. FBI agents, who had become friendly with Fratianno, also warned him that Chicago-backed hoods were following him. Fratianno decided it was time to go with the FBI and into the Witness Protection Program. Under FBI protection as an informant, Fratianno told police about the murder of Louis “Russian Louie” Strauss, a hustler and gambler who was trying to blackmail Binion. Binion went to the Los Angeles syndicate and agreed to build another casino near his own and give the mob a 25 percent interest if the problem with Strauss was solved, according to Fratianno’s book. The murder contract was handed to someone else, but after 18 months nothing was done and he was given the contract, Fratianno said. He enlisted Caifano to help, Fratianno said. He and Caifano proposed loaning money to Strauss, who had gambling debts, if Strauss would be an intermediary to extorting money from Ryan in Palm Springs, Fratianno said. That was in 1953, 10 years before Caifano did try to extort $60,000 a year from Ryan. Fratianno said Caifano dropped out of the trip supposedly to extort Ryan, but sent another hood instead to accompany Fratianno and Strauss. At a house in California, where other mobsters waited and watched, Fratianno said he and another man garroted Strauss to death. Gerald Thomas Shallow was a former Chicago police officer who also turned informant when facing stolen securities charges. He told investigators that Ryan’s name was used as bait in the December 1973 slaying of Richard Cain, Shallow’s friend and former partner on the Chicago police force. Cain had an amazing career as a double agent. He worked for the Chicago police department and as chief investigator for the Cook County, Ill., state’s attorney office, all while working for the Chicago syndicate. He was personable, flamboyant and a media favorite, leading reporters and photographers on raids. But Cain was involved in scandals over money taken from a madam, and the killing of a petty extortionist. He used police equipment to conduct lie detector tests on gangsters suspected of talking to cops, and passed on the names of those who failed to mob bosses. He was fired by the police department in 1960, but managed to get a job with the state attorney’s office. In 1964, he was fired from that job, and convicted of crimes that were later overturned. In the 1970s, Cain traveled with ex-mob boss Giancana to Mexico and other parts of the world, drumming up large-scale gambling schemes. Cain and Giancana parted company in 1973, and Cain returned to Chicago. Shallow told authorities the Chicago syndicate wanted Cain dead for making derogatory remarks about a top mob associate, said John J. O’Rourke, former FBI agent in Chicago. The former agent, in a recent interview, said Shallow admitted he and Cain killed the girlfriend of a Chicago mobster in Indianapolis in 1972 on a mob contract. In December 1973, Caifano approached Cain about the idea of killing Ray Ryan in Evansville with a rifle, Shallow told FBI agents. Cain told him “Marshall (Caifano) must be back in the good graces,” Shallow said, according to the FBI report turned over to Evansville police.
Caifano and Cain were to meet Dec. 20, 1973 at Rose’s Sandwich Shop in Chicago, but Caifano left shortly before Cain arrived. As Cain sat at a table, two men wearing ski masks and carrying shotguns entered, one stepped behind Cain, pointed a gun at his head and killed him, according to reports of the shooting. The former FBI agent said it was Shallow’s “personal opinion” that as a reward for setting up Cain, the Chicago syndicate later authorized the “contract murder of Caifano’s sworn enemy, the millionaire named Ryan.”
Alva Johnson Rodgers was nearly 50 and had spent 23 years in prison by the time he was interviewed in June of 1979, at the Federal Corrections Institute in Miami, Fla., by Evansville detective Steve Bagbey and a FBI agent. Around 1969, Johnson was serving a lengthy term in federal prison in Atlanta for possessing counterfeit money and a parole violation of a bank robbery charge. A transcript of Rodgers’ interview by police showed Rodgers was in an eight-man cell when Caifano transferred in from the Marion, Ill., federal prison. They would share a cell for about three years, according to the interview. Rodgers was familiar with case law as a jailhouse lawyer, and started working on Caifano’s case. He eventually managed to get Caifano out of jail about one year early. Rodgers said he learned about Ryan and his background, the 1949 poker game between Ryan and Nicholas “Nick the Greek” Dandolos in which Dandolos claimed Ryan cheated him out of $550,000, and the 1964 extortion trial in Los Angeles. Rodgers, in his interview with police, said Dandolos ran to Chicago “for muscle to get his money back” and Caifano got involved. Caifano was “a very vindictive guy” and obsessed with Ryan, Rodgers told police. “It ate at him (Caifano) the whole time that he was in jail, the whole time that I was with him (later) in Chicago (that) it was Ryan who was still walking around,” Rodgers said in the interview. Caifano had told him the New York mob said they would convince Ryan not to testify in 1964, Rodgers said. Ryan, through his gambling and oil deals, was acquainted with some New York mobsters over the years. But Ryan testified anyway. Caifano was released from prison in December 1972. About six months later, Rodgers was released from jail and joined Caifano in Chicago. Rodgers said Caifano was grateful for getting an early release from prison. Informants Fratianno and Rodgers told investigators about times Ryan’s name came up in Chicago shortly before the millionaire’s car bombing. Fratianno, in his book, noted he was at a restaurant in 1976 with Joey “The Clown” Lombardo, a top Chicago mob figure, Caifano and others when Caifano said he was upset that Ryan wasn’t No. 1 on the “hit parade” to be killed. Rodgers told authorities of frequent trips with Caifano, who didn’t like to drive, to a golf driving range to meet Lombardo and others where Ryan’s name came up. Rodgers, in his police interview, said Caifano “wanted to take care of Ryan when he first got out,” but that Caifano was told to leave Ryan alone. Lombardo told Caifano five or six times over several weeks that “we are taking care of it, we are working on it,” Rodgers told police. Lombardo said the syndicate had been trying for years to nail Ryan, even following him to Africa while Caifano was in jail, Rodgers told investigators. Lombardo then suggested Ryan be told to pay a settlement of $1 million to be left alone and “die a natural death,” Rodgers told police. Caifano was to receive half of the $1 million, Rodgers said. Caifano said, “Let’s take the million dollars and hit him anyway.” Lombardo said no, telling Caifano: “The people that we are dealing with, you know, the people that was going to be the in-between. If we give them our word, we are going to have to live up to it,” according to transcripts of Rodgers’ interview.
Police believe the proposal to Ryan to pay $1 million was made by Binion to Ryan probably in the spring of 1977 in Las Vegas. Binion, after Ryan’s slaying, denied to police that the meeting took place.
After his murder, Ryan’s daughter, Rae Jean, told police about a conversation with her father when he visited her July 4, 1977, in California. He said Binion told him that Caifano wanted $1 million “or steps would be taken to get even,” the daughter told investigators. Her father said he told Binion that Caifano would have to get in line behind the “G” (government), meaning the IRS, which had a federal tax court case seeking $9 million, Rae Jean Ryan said. About 3 months later, Ryan was killed in Evansville, a place the millionaire oilman and developer and his wife, Helen, called home. They could have lived anywhere in the world. The Ryans, together or separately, would spend months in Palm Springs, Africa or elsewhere, but for Helen Ryan, Evansville was the family’s base. It was where their daughter grew up and graduated from Memorial High in 1961 before going to Indiana University, Marymount College in California and eventually living in that state. “Evansville always will be my home,” a friend recalled Helen Ryan once saying. “I have too many roots here to consider another place.” Bagbey would believe that Ryan’s friendships with Frank Erickson, the king of the bookmakers, Frank Costello, a leader among the New York mobs, and possibly Giancana were “buffers,” people who were able to use their standing in the mob to prevent anything bad happening to Ryan. A former bodyguard for Ryan told investigators that when he left Ryan’s employment in Africa in the late 1960s, Ryan gave him a letter for Erickson and a message to deliver to Costello. By 1977, the “buffers” were dead, Bagbey said. Erickson died in 1968, Costello in 1972 and Giancana was murdered gangland style in 1975. Bagbey said Evansville probably was selected as the site to kill Ryan because “this was his safe haven. This was where he felt protected and this is the reason he was executed here.” Bagbey, who retired from the police department in 1999, admits the chances of someone being charged in Ryan’s murder “is very remote. That’s very unfortunate for Mr. Ryan and his entire family. “We gave it everything we had and we went down swinging.” Ryan always knew the possibility existed that the mob might kill him. In the year before he was killed, Ryan once told an employee: “They’ll get me some time, I know it.” In 1980, Caifano received a 20-year prison term for conspiracy in a scheme to peddle stolen stocks and as a dangerous special offender. Caifano was released from prison in 1991. Now 91, he lives in Florida. He did not return a phone call requesting an interview. Richard Eisgruber was an FBI agent in Evansville when Ryan was killed. Eisgruber, 63, is retired from the FBI and works security for an airline in Atlanta. The Evansville FBI office for several years had someone close to Ryan keeping track of his comings and goings, but no illegal activity was noted. Several months after Ryan was killed, another informant, this one providing information about Cleveland’s syndicate, told authorities two veteran organized crime enforcers killed Ryan, Eisgruber said. Bagbey and Eisgruber said one of the men fit the artist’s drawings of the balding man seen in the spa shortly before Ryan was killed and another drawing of the man with sideburns who was seen around Ryan’s car in the parking lot. But police never could place either of the two men in the Evansville area at the time Ryan was killed.
Eisgruber said the Ryan murder was one of the toughest cases he ever dealt with as a FBI agent. “We feel we know who did it and why it was done, but never were able to tie the knot,” Eisgruber said. “We had informant information. While that’s kind of nice to know and puts you in the right direction, it doesn’t make your case for you. “The bad guys got away with one, and that’s not good.”