When William Mastrosimone was working on the script for the 1992 mini-series "Sinatra," the singer told him a startling tale that involved Joseph Kennedy Sr., JFK, Chicago mob boss Sam Giancana and Judith Exner, Sinatra's girlfriend who was also mistress to both Kennedy and Giancana.
It was a tale of power, sex, murder, intrigue and hubris, the stuff of Greek tragedy, not to mention political and mob legend.
That story was the starting point for a new play, "Ride the Tiger," now in previews, and opening Wednesday, April 3, at New Haven's Long Wharf Theatre.
An earlier version of the work titled "Dirty Business" premiered in Florida in 2008. But Mastrosimone, (off-Broadway's "Extremities," "The Woolgatherer," and "Shivaree" which premiered at Long Wharf in 1983) says this new version steps away from docudrama and refocuses on the psyches of the high-profile characters.
The Long Wharf production stars John Cunningham as the senior Kennedy, Douglas Sills as JFK, Peter Anthony Stewart as Sinatra, Christina Bennett Lind as Exner, and Jordan Lage as Giancana. Artistic director Gordon Edelstein stages the show.
Over a diner breakfast near the meatpacking district where the theater is located, the Trenton, N. J.-born Mastrosimone, 65, talked about gaining Sinatra's trust and his own efforts to fill in the details of the story of how the singer put the Kennedys in contact with Giancana, how the Mafia's efforts in Chicago helped get Kennedy elected, how the Kennedys — once in office — betrayed that favor, and what happened after.
Short, stout and balding Mastrosimone looks like someone who could easily travel in the shadowy circles of power and intrigue, a no-nonsense sideman who would make you feel comfortable sharing a confidence, counsel or a drink.
"I found Sinatra at a time in his life when he was very willing to tell the story," he says sotto voce.
"This was a man who was 77 and he wanted to get things off his chest," says the writer. "Basically Frank was saying that Sam Giancana had the motive, the means and the opportunity to do this."
"This" meaning the 1963 assassination of the president.
The play takes place from 1960 during the presidential campaign through 1962, and presents a motive that allows the audience to project to Dallas in 1963 and imagine that Kennedy's assassin did not act alone.
The connections among the CIA, JFK and the mob is not breaking news. Members of the Giancana family have already recounted their version of the time in "Double Cross: The Explosive, Inside Story of the Mobster Who Controlled America," a 1992 book by Giancana's brother Chuck Giancana and Chuck's son Sam. Giancana's daughter Antoinette also wrote about political and mob ties in the 2005 book "JFK and Sam: The Connection Between the Giancana and the Kennedy Assassinations."
Mastrosimone is working as a dramatist, using information from Sinatra's personal perspective to imagine the behind-the-scenes power plays.
Does he believe that the well-established mob connections led to Kennedy's assassination?
"Yeah," says Mastrosimone.
It started, he says, in 1960 with the senior Kennedy — who made money in the booze business during and after g Prohibition — asking the entertainer, who was a pal to JFK, to lunch.
"Joe said to Frank, 'You know some very unsavory people in Chicago.' He never said, 'Mafia.' Joe asked Frank to go to Chicago to ask Giancana, who was an organized crime figure there, to swing the union vote Jack's way in the election."
"Sinatra went to Giancana and asked him for this personal 'favor' which was the coin of the realm in that world. The assumption was in the end Kennedy would get the labor vote and the mob would have someone in the White House."
But once elected, Kennedy's brother Robert became attorney general and launched a campaign against the Mafia by jailing, indicting and deporting mobsters all around the country.
"It was a precaution against anyone saying the Mafia got the president elected," says Mastrosimone, "and it worked."
All About Hubris
"What do you call someone who asks a favor like that and then tries to screw the Mafia?" says Mastrosimone. "Are they idiots? The Kennedys are not idiots. It's about hubris."
"Ride the Tiger" characterizes JFK as being "undisciplined, out-of-control and an adrenaline freak," says the playwright. In the play's first scene Joe Kennedy, a formidable planner who envisions a 100-year dynasty for his sons and their offspring, warns his son about his problem.
"The Kennedys cut Frank out, too," says Mastrosimone, "and that infuriated Sam who felt like he looked like a fool in front of his people — and foolish means weak and that means there's danger to his own life from his own people.
"Sam said to Frank: 'Joe knows who I am but his kids think I'm the Boy Scouts. They don't appreciate that I am a powerful man.' The last thing he said to Frank was, 'We're going to show those two brothers how the Boy Scouts keep score."
JFK was killed in 1963; his brother Robert in 1968, though Mastrosimone says the mob link to RFK's assassination is not strong. Giancana's relationship with the CIA — he was involved since the late '50s in plots to kill Cuba's Fidel Castro — has fueled a conspiracy theory about the presidential assassination.
That theory was bolstered beginning in January, 1975, when a senate committee was created, headed by U.S. Sen. Frank Church, a Democrat from Idaho, to investigate CIA and Mafia ties.
Prior to testifying, Giancana was killed June 19, 1975, in his Chicago home, from gun shots to the back of his head and in the mouth — the latter seen as a warning against talking.
Mastrosimone believes that Giancana knew his killer because the table was set for two and sausages and peppers were simmering on the stove. The writer is not sure whether the murder was a mob hit or done by the CIA.
Mastrosimone remembers a telling transcript of a wiretap at a restaurant where Giancana and another mobster were meeting. When the other mobster, who was just indicted, asked him what to do, Sam pointed to a stuffed marlin hanging on the wall. 'You see that fish up there? The only way it got caught was when it opened its [expletive] mouth.'
Power of Beauty
And as for party girl Exner who linked Kennedy and Giancana?
Compared to the other characters, "she looks like an ant next to giants," he says. "But her power was that of the Geisha Girl — the power of beauty, being subservient and possessing the ability to stop a man in his tracks with a glance. She understood that powerful men don't want powerful mistresses. They want malleable people.
"But there are things that she wants. She believes that Jack loves her and she has a future. She believes she can be First Lady, though she never says that. Still, she fights for that in her own way."
Exner wrote her own memoir in 1977 entitled, "My Story."
"I don't buy her version at all," says Mastrosimone. "It's laughable. I think she wrote that book after Sam was murdered to tell the Mafia, 'Look, I have a chance to spill the beans and I'm not going to do it. In fact, I'm going to entertain you with all this [b.s.] and lie and you will see you have nothing to fear from me.' I believe she was truly fearful for her life." Exner died in 1999 at the age of 65. Joseph Kennedy suffered a stroke in 1961 and died in 1969, living long enough to see two sons assassinated. Sinatra died in 1998 at the age of 82.
Though Mastrosimone thought Exner's version was a protective concoction he believes the behind-the-scenes story Sinatra told him for two reasons.
"When we talked about JFK his eyes welled up. He was still smarting from the betrayal 25 years later. But there was an even greater reason why I believed him. The story he told made him look bad. That tough Sinatra of popular propaganda is not in this play. In this play he gets pushed around. He's humiliated. So why would he tell this story? Because he wanted the truth to be told."
Does Mastrosimone have any fear of retribution for telling this story?
"It would look good on my resume if I ended up like Johnny Roselli in a 50-gallon drum filled with cement," he says with a small smile of the mobster known as "Handsome Johnny," a friend of Sinatra's who was called twice to Church's committee. "But the mentality of the mob has changed. They would be proud of this."
And finally, the meaning of the title of the play?
Mastrosimone says it came from Kennedy's inaugural address in which he warned countries who were gravitating toward Communism.
"Once you are riding the tiger," says Mastrosimone, paraphrasing Kennedy, "the problem comes in the dismounting."
RIDE THE TIGER runs through April 21 on Long Wharf's main stage, 222 Sargent Drive, New Haven. Tickets are $42 to $72. Information: 203-787-4282 and http://www.longwharf.org.
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