Phyllis McGuire’s Boudoir Was Bugged by FBI When She Had a Passionate Romance with an Infamous Mobster

Phyllis McGuire and Sam Giancana made up one of the most bizarre couples of the '60s as she was a singer and he was a mobster tracked by the FBI. McGuire even double-crossed the FBI.

The Isley Brothers said it best: “You never know when you’re going to fall in love.” In Phyllis McGuire’s case, the man she fell head over heels for was Chicago mob boss Sam Giancana.

PHYLLIS AND GIANCANA’S LOVE STORY

Phyllis and her older sisters, Christine and Dorothy McGuire, achieved worldwide fame in the early '50s with their singing trio, The McGuire Sisters. They stole people’s hearts with popular songs like “Sincerely” and “Sugartime” before taking some time off in 1968.

However, the trio started facing challenges, including blacklisting, years earlier due to Phyllis’ love life. In 1959, the sisters had a gig at the Desert Inn in Las Vegas, one of Giancana's many casinos.

During the McGuires’ performance, he supposedly was immediately intrigued by “the one in the middle:” Phyllis. She happened to be a big blackjack player, and she had run up a $20,000 debt at the tables.

Giancana heard about it, but instead of making sure the money was paid, he told the casino’s frontman to “eat the marker,” meaning he should just forgive the debt. At the time, neither Phyllis nor her sisters knew who Giancana was.

He introduced himself as Sam Flood, so nobody could have imagined he was the same man who drove for Al Capone in Chicago, had been arrested several times, and was linked to murders and illegal gambling.

Giancana and Phyllis began dating shortly after, but their romance was a surprise to many, especially because she and her sisters were considered “nice girls” and American icons.

According to retired FBI agent William Roemer, power was what led Phyllis to Giancana. Rohmer described the mobster as an ugly and brutal man who lacked culture but had enough power to corrupt people.

The FBI was the most significant challenge in their romance.

As a lover, though, Giancana was attentive. He would send Phyllis jewelry and furs and even meet her overseas when the trio had to perform abroad. Those close to the couple were sure they loved each other. Roemer explained:

“It’s amazing that it ever took place. She had everything. She had beauty. She had money. Yet, she fell in love with this gangster. I could never figure it out.”

Phyllis admitted that she just liked him, and he was nice to her. Before finding out who he really was, some of her friends told her that Giancana was a murderer, but she wondered why he was still on the street if he had really done the things what people said he did.

FACING COMPLICATIONS

Eventually, Phyllis learned the truth, but it was too late as she was already in love. She thought about breaking up with him a couple of times, especially because her parents couldn’t accept their relationship.

Personal matters aside, the FBI was the most significant challenge in their romance. Roemer himself was in charge of investigating Giancana, and he went as far as following him into men’s rooms and bugging Phyllis’ boudoir.

If that wasn’t enough, the FBI wiretapped the couple’s motel room in Phoenix in 1961. Later that year, they staged a confrontation at Chicago-O’Hare International Airport.

As expected, Phyllis was questioned about her partner’s criminal activities, but she claimed she didn’t know anything. She pointed out that Giancana was “very protective” of her and wouldn’t talk about what he and his organization did.

FBI’S INVOLVEMENT

The FBI probably believed that Phyllis would help them catch her mobster boyfriend, so they urged her to cooperate in the investigation. In 1965, she testified before a grand jury in a racketeering case against Giancana.

Although Phyllis confessed that she was aware of his reputation and still chose to date him, she remarked she didn’t know anything about his crimes. That really hurt her and her sisters’ careers.

”[Phyllis] never cooperated with us. She double-crossed us, really."

Her comments were so frowned upon that they were blacklisted on TV for a while. It was unacceptable for one of America’s sweethearts to be with that man.

Apart from that, her brother-in-law gave her an ultimatum: if she didn’t leave Giancana, The McGuire Sisters would be over. Phyllis was too in love and couldn’t do it, though.

Also, in 1965, the FBI granted Giancana immunity so that he couldn’t plead the 5th Amendment and stay silent in court. Even with the agreement, he didn't say a word and was sent to Cook County Jail for contempt.

GIANCANA’S FINAL YEARS

The mob exiled Giancana after he spent one year in prison, so he moved to Mexico and South America, where he set up some gambling operations and became rich again. The mob wanted part of his earnings, but Giancana didn’t believe they deserved it.

According to Roemer, Giancana felt pushed out and considered that they had nothing to do with the money he made. Years later, he moved back to Chicago, and the mob knew it.

In 1975, a person got into Giancana’s basement and killed him in a still-unsolved case. Even after all the ordeals, Phyllis was still in a relationship with Giancana at the time.

The singer once confessed that she would not change anything about their romance. In fact, she stayed close to some of his family members, including his three daughters. It is important to point out that Phyllis never betrayed Giancana. Roemer said:

“She said she would [betray him], but she never did. She never cooperated with us. She double-crossed us, really."

Phyllis, who supposedly received all of Giancana’s money after his passing, died at her Las Vegas home on December 29, 2020. Apart from her early marriage to Neal Van Ells, she never remarried.

The rest of the McGuire Sisters passed away years before Phyllis did — Dorothy died in 2012 and Christine in 2018. They kept performing together in nightclubs and other venues until 2004. Rest in peace.