Phyllis McGuire, singing star and Sam Giancana paramour, dies at age 89

Phyllis McGuire, singing star and Sam Giancana paramour, dies at age 89

Las Vegas resident’s career was damaged by relationship with Chicago Outfit boss in 1960s

Chicago Outfit boss Sam Giancana and Phyllis McGuire pictured together in London in 1961. Corbis via Getty Images

Phyllis McGuire, the last of the popular McGuire Sisters singing trio and onetime girlfriend of Chicago Outfit boss Sam Giancana, died December 29 at her Las Vegas home. She was 89.

The McGuire Sisters, whose sweet harmonies made them big stars in the 1950s, had chart-topping hits such as “Sincerely” and “Goodnight, Sweetheart, Goodnight,” which recalled an era, as the New York Times put it, of “car fins, charm bracelets and duck-tail haircuts.”

The McGuire Sisters — Christine, Phyllis and Dorothy — were a popular trio in the 1950s and 1960s. They had two No. 1 songs, “Sincerely” in 1955 and “Sugartime” in 1957, as well as many other Top 40 hits. Image from Billboard magazine, 1964. Courtesy of Wikimedia Commons.

In 1952, barely into her 20s, McGuire married broadcaster Neal Van Ells. This was the same year she and her sisters began their musical ascent after winning the Arthur Godfrey Talent Scouts competition. By 1956, McGuire and Van Ells ended their marriage without children.

The daughters of an Ohio steelworker father and minister mother, Phyllis, Dorothy and Christine McGuire ranked with the top stars of the ’50s and early ’60s. Phyllis was the youngest of the trio and the lead singer.

For some fans, however, Phyllis McGuire’s wholesome image seemed less glossy after reports surfaced about her relationship with Chicago Outfit boss Sam Giancana.

By the time McGuire met Giancana in Las Vegas in 1959, he’d had a long history in Chicago’s underworld and as a force on the national criminal scene. In the early ’60s, Giancana was part of an unsuccessful alliance between the Mafia and the CIA to assassinate Cuban leader Fidel Castro.

Around the time Giancana met Phyllis McGuire, he and President John F. Kennedy were involved with the same woman, Judith Campbell Exner. At some point, Campbell Exner also was in a romantic relationship with stage and screen star Frank Sinatra.

Cal-Neva Lodge

During this time, federal agents were tracking Giancana’s movements, including when he traveled to different cities to meet up with McGuire where she was performing. In 1963, this led to a scandal that cost Frank Sinatra his ownership of the Cal-Neva Lodge on the north shore of Lake Tahoe.

That summer, Giancana stayed with McGuire in one of the lodge’s chalets while she and her sisters were there to perform in the Celebrity Room. Giancana is believed to have had a hidden ownership in the now-shuttered Cal-Neva Lodge.

Giancana wasn’t supposed to be there at all. His name was in the Nevada Gaming Control Board’s Black Book, prohibiting him from entering any casino statewide. When a Nevada gaming regulator confronted Sinatra about this, Sinatra lit into the state official, calling him a “crippled S.O.B.” Because of childhood polio, this state official used a cane.

Within months, Sinatra forfeited his ownership in the Cal-Neva, as well as a 9 percent interest in the Sands Hotel in Las Vegas. Sinatra and Giancana blamed each other for the incident.

McGuire once said she had known about Giancana’s underworld reputation but not what those activities entailed, according to the New York Times. The relationship caused some heartache in her family, she said.

“It makes me look terrible,” McGuire said of the relationship. “It would be different if I were on my own, but I’m not a single — I’m part of a trio. My sisters and my parents — they’re brokenhearted about this.”

McGuire and her older sisters performed together until 1968, when the other two took time off to focus on their families. Phyllis continued performing from her base in Las Vegas.

In 1975, Giancana, age 67, was shot to death in his home in Oak Park, Illinois, a Chicago suburb. No one was ever arrested in the killing.

His death had a permanent impact on McGuire. “The two great losses of my life were my father and Sam,” she said.

The McGuire Sisters got back together in 1985 and toured for about 20 more years, performing in casinos and nightclubs. Phyllis McGuire added impersonations of other singers to the show.

Phyllis McGuire’s sisters preceded her in death, Dorothy in 2012 and Christine in 2018.

Bugging Dan Rowan

While Giancana had multiple affairs while he was with McGuire, he was not enthused about her doing the same. Giancana’s accomplices in the plot to assassinate Castro were fellow mobster Johnny Rosselli and private investigator Bob Maheu, who served as the liaison between the Mob and CIA. In his memoir, Maheu recalls that while the three men were meeting in Miami to discuss how to kill Castro, Giancana wanted to take off for Las Vegas immediately but the CIA vetoed the idea.

“It seemed that Giancana was upset about Phyllis,” Maheu wrote. “He had heard that she had been dating the comedian Dan Rowan while he and partner Dick Martin were appearing at the Desert Inn. Since Sam couldn’t go in person, I agreed to at least arrange a tail to be put on Rowan.”

Maheu hired a private eye to check on the situation in Las Vegas. The private eye placed an illegal tap on Rowan’s phone and got caught. He had left his monitoring equipment unattended in a nearby hotel room where a maid discovered it and reported it.  “Just why he thought tapping Rowan’s phone would help determine details about his love life, I’ll never understand,” Maheu wrote.

Bob Stupak

In the 1990s, McGuire and Las Vegas casino owner Bob Stupak became a couple. In an interview with Las Vegas journalist John L. Smith, Stupak said: “I guess Phyllis is my one big love affair since I’ve been in town. It’s unexplainable. Things happen. I don’t know how they happen. It was completely unexpected. I’d never been with someone who was an entity in themselves, and Phyllis definitely was an entity in herself.”

The relationship with McGuire had a side benefit for Stupak: It enhanced his credibility in the community at a time when he was trying to raise funds to build the Stratosphere Tower.

In 1995, Stupak was involved in a serious motorcycle accident that left him in critical condition at a Las Vegas hospital. His face did not fare well in the crash, with many cuts, broken bones and missing teeth. His skull was fractured, and both his arms and a leg were broken. He was bleeding profusely.

Phyllis McGuire soon was at his side. According to John L. Smith, “Phyllis McGuire took up a vigil at the trauma center and later followed Stupak to the hospital’s Intensive Care Unit, where she read to him daily. She remained by his side for weeks.”

After five weeks, Stupak finally opened his eyes, although he still was out of touch. “Bob was slinging and flinging his arms trying to break out of the restraints,” Phyllis told Smith. “I call him the warrior of warriors. I’ve never seen anyone fight so hard to stay alive.”

Stupak, who achieved his dream of opening the Stratosphere Tower, died of leukemia in 2009.

In later years, McGuire’s companion was a petroleum company owner, Edward Mike Davis, known as Tiger Mike. According to the Las Vegas Sun, Davis was a high school dropout regarded in one media account as “pugnacious and profane.” He died in 2016.

Barbara Walters interview

In 1989, ABC News reporter Barbara Walters conducted an interview with McGuire at her Las Vegas home in the exclusive Rancho Circle gated neighborhood on Rancho Drive. While Walters marveled at the 28,000-square-foot mansion, with its 45-foot replica of the Eiffel Tower, lavish furnishings and pricey dress, shoe and jewelry collections, she also asked McGuire about her relationship with Giancana.

McGuire said when she met Giancana in 1959, she was not aware of his prominent role in organized crime. “When I met him, I did not know who he was,” she said. “And he was not married, and I was an unmarried woman. And according to the way I was brought up, there was nothing wrong with that. I didn’t find out until some time later really who he was. And I was already in love.”

Phyllis McGuire lived in a mansion in the exclusive Rancho Circle neighborhood in Las Vegas for more than 50 years. She died at home last week at age 89.

McGuire acknowledged her relationship with Giancana damaged the singing trio’s career, and she considered breaking it off with him as a result. “I tried twice but it didn’t work,” she said, because of her love for the widowed crime boss.

Adding to the difficulties for Phyllis and her sisters, the FBI was keeping its eye on her. She was called before a grand jury to testify in 1965, but she says didn’t have a lot to say because Giancana didn’t talk with her about his activities. “He was very protective of my not being involved with any of whatever he was doing,” she told Walters.

McGuire explained that wise investments in oil and gas, not the proceeds of her singing career, were the reason she owned a mansion and wore rings and earrings worth millions.

In a 1989 Vanity Fair interview with the writer Dominick Dunne, McGuire said Giancana was the “greatest teacher I ever could have had.” 

“He was so wise about so many things,” she said.

McGuire’s relationship with Giancana was the subject of the 1995 HBO movie Sugartime. This is also the title of one of the McGuire Sisters’ biggest hits. McGuire panned the biopic as wildly inaccurate.

Christmas parties

Oscar Goodman, former Mob defense attorney and three-term mayor of Las Vegas, has fond memories of the Christmas parties McGuire threw at her palatial home.

“Carolyn and myself were always invited to her beautiful home in Rancho Circle for a Christmas event,” Goodman said. “She always had an eclectic group of friends. Kirk Kerkorian was there. Paul Fisher, who makes the space pens, was there. Robert Goulet and his wife, Vera, were there. Robert Maheu was there. It was a very joyous occasion when we saw her socially.”

Goodman never served as an attorney for McGuire. “I never saw her out of her home, other than when she was performing,” he said. “I think she was very, very private.”

For Goodman, McGuire embodied the golden age of Las Vegas, before megaresorts towered over the Strip and suburbs sprawled into the foothills. 

“It was a different town then than it is today. I loved it back then. You felt very close to these people and were part of the history of the town.”

Geoff Schumacher is vice president of exhibits and programs for The Mob Museum. Larry Henry, a longtime journalist, writes the Mob in Pop Culture monthly blog for the Museum.