Childhood is, or should be, a time of innocence, and for a while that is the way it was for brothers Michael Jr. and Jeffrey Gentile. And then a pistol fell out of a coat.
“We were taking the coats from people who had come over to visit our parents and this gun just dropped on the floor,” says Michael. “For us it wasn’t a matter of, ‘Oh my God, look, a gun!’ but, ‘Hey, we better figure out which coat this fell from and put it back.’”
The brothers were born 14 months apart in the mid-1950s, and grew up in the western suburbs and everything was just fine for a time, or as Jeffrey puts it, “just like episodes of ‘The Wonder Years’ until they started to get interrupted by episodes of ‘The Sopranos.’ ”
As they write in their book
, “
Mob Adjacent: A Family Memoir”: “Once Michael and I started paying attention, the veneer that wrapped around our family fiction cracked, and there was no putting it back together. One day you’re a kid learning to read; the next you’re reading the newspaper, and there’s an article about the man who came to dinner last week. Pictures, too. Yup, that’s him. The newspaper said he’d been indicted for running a suburban gambling ring and was looking at five years in prison.”
The man who came to dinner remains nameless but the names of many of the others who pepper the book’s pages and frequented the brothers’ lives read almost like an old most-wanted list.
“Through geography and happenstance, our father grew up and knew well the post-Capone generation of Chicago criminals and crime bosses,” says Michael Jr. “They were his friends.”
The names of those people, some with well-known nicknames, pop from the pages:
Manny Skar,
Richard Cain,
Joey “The Clown” Lombardo, Frank “Skip” Cerone and his brother James “Tar Baby” Cerone and their cousin “
Jackie the Lackey” Cerone.
The brothers’ grandfather came here as a 2-year-old from Italy in 1896, settling with his parents and siblings in the then heavily Italian neighborhood around Grand Avenue and Aberdeen Street. After he helped a neighbor fight off two men who were attacking him, that man, a crime figure named Vincent Benevento, conferred on him the sort of respect and supplied the connections that can go a long way in Chicago.
He had a son named Michael (in 1929), the father of Michael Jr. and Jeffrey, and together they worked in the produce business. Then the son went to war (Korea) and afterward, with the help of some by-then nefarious childhood friends, opened a bar. He married (a woman named Mary Ann) and started a family. The Gentile brothers have a sister named Lisa.
“My dad was kind of the go-to guy for his friends,” says Jeffrey. “He was always clean as a whistle and good at what he did and so when a place was in trouble, my dad was called in.”
And so it was that in the early 1960s, he was running a place called Orlando’s Hideaway, part of a notorious strip of entertainments along Mannheim Road in the near western suburbs. Those of a certain age are likely to remember the fancy hotels, nightclubs and restaurants of that strip, and perhaps some of the illegal gambling and prostitution activities too, that comprised what was known as “Glitter Gulch,” a sort of mini Las Vegas.
It was at Orlando’s where the brothers met “a small, quiet, balding man, always perfectly tailored.” The boys were told to address him as “Mr. Sam.” He was
Sam Giancana, the head of the Chicago outfit from the mid-1950s to the mid-1960s.
Giancana, often known as “Momo,” used Orlando’s as a meeting place. The brothers were there when
Frank Sinatra came to call and, they write, “We heard an unforgettable explosion as Mr. Sam raged at Sinatra” — about a Nevada casino deal that supposedly involved Joseph Kennedy, father of JFK, a Sinatra pal. “We have never seen anyone so angry before or since. Snarling, really. Spitting mad. Literally. Red face. Eyes bulging. Insane. Terrifying.”
That is but one of the lively anecdotes in “Mob Adjacent,” a book that came to life after Michael Jr., who has had a long career in the produce business, produced and hosted a 10-part series of short YouTube videos about his family.
These premiered in November 2016. “I thought that the videos were good but that they were only a half effort,” says Jeffrey. “I always wanted to write a book about our family and so Michael and I began to collaborate, to share memories and stories.”
The foundation for the book was letters and journal entries that Jeffrey had been keeping for decades. To flesh those out the brothers talked, often for more than 14 hours at a stretch, at Michael’s home here and Jeffrey’s in Pasadena, Calif.
“Mob Adjacent” is a fine and lively book, one that gives a solid and not overwhelming history of organized crime in these parts, and offers a very detailed narrative of their family and their own lives. It is frank and honest and surprisingly amusing.
“Our lives are the result of geography and happenstance,” says Jeffrey. Or, as he writes in the book, “Being mob adjacent meant we got the best seats in the house. It also meant we got to go home after the show.”
Their father died in 1995. At his wake, Jimmy Cerone approached the open casket, patted the corpse’s cheek and whispered into the coffin, “You were a good boy.”
His sons do justice to their father’s life and this project has made them appreciate one another. “Writing this book gave us a greater understanding of who we are and where we came from,” says Michael.
It has also given them something of a cottage industry. At their website mobadjacent.com, you will find a way to order the self-published book, see the video segments and purchase all manner of items, from an array of T-shirts to shot glasses, pens and mugs. The brothers have written a pilot episode for a television series that they are shopping around to agents and producers.
“It is a sitcom based on our lives,” says Michael. “But it could also be a drama.”
Thanks to
Rick Kogan.
1930: 
1978: Six burglars who struck at mob boss 
