‘Sugartime’ revisited: Remembering a Las Vegas hall-of-famer By John L. Smith, CDC Gaming Reports January 13, 2021 at 8:00 pm Singer Phyllis McGuire, who died just before New Year’s in Las Vegas at age 89, never ran a casino – but there was a time she turned the gaming industry upside down. As a member of the ‘50s sweethearts The McGuire Sisters and as a solo act, she stopped regularly performing years ago. But I can attest that she never lost her magic whether onstage or over a long-distance line. The McGuire Sisters reeled off a string of pop hits as America’s sweethearts but saw their celebrity overshadowed by Phyllis’ notorious affair with Chicago mob boss Sam “Momo” Giancana. There’s something about keeping company with the head of the Outfit that raised eyebrows with those infatuated with the singers of such hits as “Sincerely,” “Sugartime,” “Goodnite, Sweetheart, Goodnite,” and “Something’s Gotta Give.” Singer Phyllis McGuire, the youngest of The McGuire Sisters Like other great entertainers of a previous generation, it’s hard to quantify just how big The McGuire Sisters were in the public eye. They piled up six gold records and dominated the airwaves through most of the 1950s, but time and rock weren’t kind. Phyllis was a survivor of changing musical tastes and kept on working even after Giancana’s violent demise. That alone would be noteworthy, but the fact she did so with such style is what sets her apart in my mind. It’s why she belongs in the great Las Vegas Entertainment Hall of Fame, the one that should be built as a reminder that the glitzy casinos of past and present at their best haven’t been so much about gambling as fantasy. If Hollywood is the great dream factory, then Las Vegas is its roadshow. To me, McGuire will always be a kind of Vegas princess from the golden era, the sort of woman who lit up a room just by entering it – perhaps with the help of a shimmering gown and diamond ring big enough to choke Secretariat. Her liaison with Giancana in Chalet 50 of Lake Tahoe’s Cal Neva Lodge and casino in July 1963 rocked the gaming world. Giancana was a member of Nevada’s then-new “Black Book” of persons banned from setting foot in a casino. His presence on the property was a reminder to the nation that the legal casino industry still had a long way to go before any sober soul could call it legitimate. In Las Vegas, Phyllis lived in a Rancho Circle mansion that was every inch a testament to her sense of style and personality. I got to know her a bit when she was being pursued by the indefatigable casino man Bob Stupak. They eventually became a couple. She affectionately called Stupak her “Peck’s Bad Boy.” You’ll have to look it up. Stupak was more than smitten, sending her a truckload of roses – and of course, calling the press to take note of his undying affection for the Vegas princess. But Phyllis was more than that. She enjoyed the connections she’d made many years earlier in the entertainment business and through her relationship with Giancana. Phyllis was remarkably well connected, trusted in many intriguing rooms from Chicago to Atlantic City if you catch my drift. With the Stratosphere tower project unfinished and Stupak running out of money, the seat-of-the-pants businessman from Pittsburgh searched frantically for funding sources. His hustler’s reputation and mixed track record with the Gaming Control Board didn’t exactly inspire confidence with banks and conventional lending sources. So he turned to Phyllis and the king of Las Vegas intrigue, Bob Maheu, to search for investors. The project all but busted out Stupak, but it was finished and remains a remarkable Las Vegas story that I chronicled in my 1997 book No Limit. Stupak was a one-in-a-million character. During the research of the book, I repeatedly attempted to interview Phyllis about her relationship with Stupak. She played coy for the longest time, then called me one night after a show in Chicago. Giddy from a little champagne and a lot of applause from a packed showroom, she sang “Blue Skies” over the phone. By the end of the song, I was ready to send the roses. Note: For more on Bob Stupak, read “No Limit: The Rise and Fall of Bob Stupak and Las Vegas’ Stratosphere Tower.” John L. Smith is a longtime Las Vegas columnist and author. Contact him at firstname.lastname@example.org. On Twitter: @jlnevadasmith.