His Cheating Heart
Evansvillians old enough to remember Oct. 18, 1977, will recall the day our sheltered city experienced its brush with the Mob. A car bomb exploded outside of Olympia Health Spa (on Bellemeade Avenue just east of Green River Road) shortly after 1 p.m., damaging a nearby apartment building, hurling debris nearly a football field away, knocking out power on the Southeast Side of town, and killing the Lincoln Continental Mark V’s occupant, local oilman Ray Ryan.
Ryan, described by some as a “larger than life character,” traveled often and lived the lifestyle of the rich and deceptive, the former earning him friendships with some of Hollywood’s greatest star power of the day — Dean Martin, Frank Sinatra, Bing Crosby, Bob Hope — and the latter connecting him with gangsters such as Frank Costello and Frank Erickson. These relationships were further strengthened through his partnership with actor William Holden to develop the Mount Kenya Safari Club in east Africa, a playground for the rich and famous and high-ranking members of organized crime.
Ryan’s murder intrigued Steve Bagbey, a 29-year-old patrolman working in the detective office who arrived on the scene that afternoon. Bagbey would eventually become the lead investigator in the case, heading across the country and back in search of answers (“Ray Ryan Unsolved,” Evansville Living, Nov/Dec 2004). In a 2002 interview with Evansville Courier & Press reporter Herb Marynell, Bagbey said, “Raymond John Ryan from Watertown, Wis., was one of the most fascinating guys I never met.”
In their manuscript The Mob Murder of America’s Greatest Gambler, Herb Marynell and Steve Bagbey reveal Ray Ryan’s wagering penchant.
Chapter 38: Cheating Bookies
Ray Ryan already had headed west in the late 1940s to Los Angeles, Hollywood, Las Vegas, and Palm Springs. In LA, he rented a suite at the Beverly-Wilshire Hotel for extended periods. Old and newly acquired friends stopped by. Card-playing went on all hours of the day, and he was betting heavily on horse racing. No one could miss him.
Allen Smiley, always looking for the next rich “sucker” to take for a bundle, heard of Ryan’s heavy betting and asked about him. Smiley once chaperoned a wealthy oilman to the New Orleans-area Beverly Club owned by Frank Costello and Philip “Dandy Phil” Kastel, then to a Las Vegas casino, and finally a gambling den in the Midwest. In the process, the oilman lost “a small fortune” of $100,000 or more in each place. Smiley hoped Ryan might be his next victim.
Tommy Guinan, whose sister was Prohibition-era actress and New York nightclub hostess Texas Guinan, knew Ryan betted as much as $125,000 a day, but warned Smiley to stay away from him. Ryan liked to place large bets at post time and often made a killing when he could get a bet down.
Ryan, hoping an unsuspecting bookie might be willing to accept his bets after post time, developed elaborate schemes to learn the race winners. One scam was to sequester himself in the shower in his hotel suite while his friends — gamblers and bookies — waited in the living room to go to the track. Meanwhile, Ryan sneaked in a phone call to a spotter at the track to find out who had won the first race.
When he left the bedroom, Ryan apologized for making the guys miss the first race, adding he really had a favorite horse he wanted to bet on. Usually one of the waiting bookies — certain Ryan had no idea who actually won — accepted his bet on the race. Ryan picked up thousands of dollars in the process.
Another scam involved his frequent lunches with bookies, who never turned down a meal with one of their biggest bettors. They’d meet before the races began and never were out of each other’s sight before lunch.
As the waiter passed out the menus, inside Ryan’s was a piece of paper listing the winners of the first two or three races. Ryan pretended to scan the menu while memorizing the note. He earlier had slipped the waiter $500 to pass the information to him.
During lunch, the men talked about a lot of things, and eventually Ryan casually mentioned he’d like to place bets on the early races at the track. Some bookies never suspected anything, believing he couldn’t know which horses won because he was with them the entire time. Bookies who took the bets of $10,000 or more on each race soon discovered lunch was a costly affair.
That wasn’t cheating to Ryan. It was just being smart enough to get the edge on the next guy — something they were trying to do to him.
Early on, he managed to pull off the charade numerous times, but later most bookies shied away from taking his bets after post time regardless of whether they had been with Ryan the entire day. He never bet huge bundles of cash on the scams ($10,000 wasn’t a large bet for Ryan) because he considered it a practical joke rather than a money-making scheme. He loved to amuse his friends with stories of how he put one over on a bookie.
His enormous personal appeal also brought him into contact with movie stars, studio executives, and producers in LA and Palm Springs. Hollywood folks flocked to Palm Springs to get away from prying eyes and the hubbub of sprawling LA. The pace in Palm Springs was slower, the weather milder, and no one cared what anyone did behind the walls and iron gates of the mansions.
Ryan relished being around movie stars and executive moguls, cementing friendships with Johnny Rosselli (an influential mobster) and other hoods who made California their empire and Palm Springs their pleasure palace, and drawing into his sphere of influence wealthy businessmen in the relaxed atmosphere of dinners and galas in Palm Springs and LA. Ryan would collect hundreds of photographs of himself with movie stars and other new friends.
One of Ryan’s famous acquaintances was Phil Regan, a well-known tenor who had appeared in two dozen motion pictures in the 1930s and 1940s. Regan had just starred in the role of Lucky Ryan in the 1946 movie “Sweetheart of Sigma Chi” when they met. Born in 1906, Regan grew up in a cold-water flat in Brooklyn, the son of Irish immigrants. He later joined the New York City Police Department, and at a party given by a vaudeville producer, he went to a piano and sang. A radio executive hired him and his career as the “singing cop” began.
Through Regan, Ryan would meet young multimillionaire Chicago businessman Ralph E. Stolkin, and that partnership would lead to one of the largest oil strikes in West Texas, the financial backing of a Dean Martin/Jerry Lewis movie, and going head-to-head with Howard Hughes for ownership of a major Hollywood studio
Editor’s Note: Herb Marynell and Steve Bagbey currently are seeking a publisher for the 309-page manuscript.