Former Winnipegger Al Smiley had close association with “Bugsy” Siegel


Al Smiley

On the evening of June 20, 1947, less than six months after he opened the Flamingo Hotel-Casino in Las Vegas, Ben “Bugsy” Siegel died in a barrage of bullets through the front windows while sitting on a couch in his Beverly Hills mansion at 810 Linden Drive.Assassinated at the age of 41, Siegel was one of the USA’s most notorious gangsters.
Al Smiley (1907-1984), a former Winnipegger, was with Siegel that evening.
“My dad was seated inches away from Siegel, on the sofa, and took three bullets through the sleeve of his jacket,” said Luellen Smiley, a creative non-fiction writer, award-winning newspaper columnist and Mob historian, who lives in Sante Fe, New Mexico.
She consented to an interview with The Jewish Post & News earlier this winter.
“He was brought in as a suspect. His photograph was in all the newspapers,” said Luellen.
“He was the only nonfamily member who had the guts to go to the funeral.”
So who was Al Smiley?
Born in Kiev, Ukraine in 1907 as Aaron Smehoff, Smiley and his family – father Hyman, mother Anne, sister Gertrude (who became a school teacher and lived in Winnipeg until her death many decades later), brothers Samuel and Benjamin – immigrated to Winnipeg when he was five, said Luellen Smiley, during a recent telephone interview with this reporter from her home in Sante Fe, New Mexico.
“My grandfather was a kosher butcher and delicatessen owner,” she continued, noting that the family home and butcher shop was located at 347 Aberdeen Avenue.
“He maintained an Orthodox household and expected that his eldest son would become a rabbi. But, my father was rebellious and interested in sports, especially hockey.”
This caused conflict between the willful youth and his rigid, religious father.
So, the teenager fled Winnipeg for greener pastures in Detroit, Michigan via Windsor, Ontario in 1923.
He got a job travelling with the Ringling Brothers Circus and ended up in California where he was arrested for a drugstore robbery in San Francisco and sent to Preston Reformatory School in Ione, California, Luellen noted.
“It was there that he met legendary movie director Cecil B. DeMille,” she said.
“He was doing some sort of research for a movie. My father asked him for a job in the movie industry upon his release, and DeMille agreed. He found my dad work in a wardrobe department.
He later became a property man, then a grip, the person in charge of production on a set, and eventually a producer.”
He befriended celebrities like George Raft, Eddie Cantor, Clark Gable, Lauren Bacall, along with such gangster associates as Ben Siegel.
“I’m pretty sure Dad met Ben through George Raft,” Luellen Smiley speculated.
With Siegel’s help he opened a nightclub in L.A. sometime in the late 1930s.
Smiley would later tell his daughter that Siegel was “the best friend I ever had.”
In her soon-to-published memoir, excerpts of which she agreed to let this newspaper print, Luellen Smiley reveals the conflicted feelings she had growing up, and into later life too, about her father:
“Some children are silenced. The pretense is protection against people and events more powerful than them. As the daughter of Allen Smiley, associate and friend to Benjamin ‘Bugsy’ Siegel, I was raised in a family of secrets.
“My father is not a household name like Siegel, partly because he wore a disguise, a veneer of respectability that fooled most. It did not fool the government.
“When I was exposed to the truth by way of a book, I kept the secret, too. I was 13. My parents divorced, and five years later, my mother died. In 1966, I went to live with my father in Hollywood. I was forbidden to talk about our life: ‘Don’t discuss our family business with anyone, and listen very carefully to what I say from now on!’ But one night, he asked me to come into his room and he told me the story of the night Ben was murdered.
“When I was spared death, I made a vow to do everything in my power to reform, so that I could one day marry your mother.
“Ben was the best friend I ever had. You’re going to hear a lot of things about him in your life. Just remember what I am telling you; he’d take a bullet for a friend.
“After my father died, I remained silent, to avoid shame, embarrassment and questions. But 10 years later, in 1994, when I turned 40, I cracked the silence. I read every book in print – and out of print – about the Mafia. Allen Smiley was in dozens. He was a Russian Jew, a criminal, Bugsy’s right-hand man, a dope peddler, pimp, a racetrack tout. I held close the memory of a benevolent father, wise counselor, and a man who worshipped me.
“I made a Freedom of Information Act request and obtained his government files. The Immigration and Naturalization Service claimed he was one of the most dangerous criminals in the country. They said he was Benjamin Siegel’s assistant. They said he was poised to take over the rackets in Los Angeles. He didn’t; he sold out his interest in the Flamingo, and he went to Houston to strike oil. I put the file away, and looked into the window of truth. How much more could I bear to hear?
“He stowed away to America at 16, and was eventually doggedly pursued for never having registered as an alien. He had multiple arrests – including one for bookmaking in 1944, and another for slicing off part of the actor John Hall’s nose in a fracas at Tommy Dorsey’s apartment. He met my mother, Lucille Casey, at the Copacabana nightclub in 1943. She was onstage, dancing for $75 a week, and my father was in the audience, seated with Copa owner and mob boss Frank Costello.
“‘I took one look, and I knew it was her,’ was all he had told me on many occasions.
“On a trip to the Museum of Motion Pictures Arts and Sciences in Los Angeles, I was handed a large perfectly pristine manila envelope, and a pair of latex gloves with which to handle the file. Inside were black and white glossy MGM studio photographs, press releases, and biographies of my mother’s career in film, including roles in ‘The Secret Life of Walter Mitty,’ ‘Ziegfeld Follies of 1946,’ ‘Meet Me in St. Louis’ and ‘Harvey Girls.’ She was written up in the columns, where later my father was identified as a ‘sportsman.’ The woman who pressed my clothes, washed my hair, and made my tuna sandwiches was an actress dancing in Judy Garland musicals, while her own life was draped with film noir drama.
“My father wooed her, and after an MGM producer gave her an audition, he helped arrange for her and her family to move to Beverly Hills, where she had steady film work for five years. He was busy helping Siegel expand the Western Front of the Costello crime family and opening the Flamingo casino in Las Vegas. They were engaged in 1946.
“Still, the blank pages of my mother’s life did not begin to fill in until I met R.J. Gray. He found me through my newspaper column, ‘Smiley’s Dice.’
“One day last year, R.J. sent me a book, ‘Images of America: The Copacabana,’ by Kristin Baggelaar. There was my mother, captioned a ‘Copa-beauty.’ Kristin organized a Copa reunion in New York last September. I went in place of my mother, but all day I felt as if she was seated next to me. I fell asleep that night staring out the hotel window, feeling a part of Manhattan history.
“Now, the silence is over. I don’t hesitate to answer questions about my family. I have photographs of Ben Siegel in my home in Santa Fe, NM, just as my father did. Every few months I get e-mails from distant friends, or people who knew my dad.
“It seems there is no end to the stories surrounding Ben and Al. I am not looking for closure. I’ve become too attached to the story. To me, he was a benevolent father, a wise counsellor and a man who worshipped me.”
Luellen Smiley can be contacted via email:

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Category: Features


  1. Can I simply say what a comfort to discover someone who really
    understands what they are discussing online. You definitely realize
    how to bring an issue to light and make it important.
    More and more people must check this out and understand this side of the story.
    I can’t believe you’re not more popular since you definitely
    have the gift.


    1. Darling
      I arrived on Wednesday!! I am perched on the mountains and trying to
      grasp this transition. I will see you when you come to LA. Are you going to Phily soon?
      Love you and can’t wait for our long awaited rendezvous


  2. Lovely, Lou Lou. Very lovely. Tying the pieces together, understanding the gift you have been given, not through the closure you once sought (as you mention), but a continuous and fascinating living drama.

    Fact is, through the amazing life of your parents, you were gifted with a story to tell, a history to share, and a compelling identity of your own. And we love you because of it all.



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