We’re diving deep into the life and legacy of one of the most notorious figures in the history of the Genovese Crime Family—Thomas “Tommy Ryan” Eboli. And who better to tell that story than his own son, Xavier Eboli?

Xavier Eboli, a Marine Corps veteran and author ofThe Boss in the Shadows: The Life and Death of Thomas ‘Tommy Ryan’ Eboli, joins me for an incredible two-hour conversation.

Together, we explore what it was like growing up as the son of a powerful mob boss, tracing his father’s journey from a young boxer and as a boxing manager to a feared underworld leader whose career ultimately ended in a hail of bullets in 1972.

We’ll also discuss Xavier’s own life—his time in the Marines, his evolving relationship with his father, and the lasting impact of his father’s murder.

Along the way, we touch on key figures like Vito Genovese, Charles “Lucky” Luciano, Vincent ‘The Chin’ Gigante, Philip ‘Benny Squint’ Lombardo, and even Hollywood connections to Al Pacino and Al Lettieri.

So grab a drink, settle in, and get ready for an intimate, firsthand look at the life and death of one of the mob’s most infamous figures.

This is Xavier Eboli’s story, in his own words.

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We discuss many topics including:

• Xavier's upbringing and relationship with his father
• The early life of Thomas “Tommy Ryan” Eboli in Chicago and then New York
• Thomas Eboli's relationship with his father and eventual introduction to his Cosa Nostra mentor, Vito Genovese
• Eboli's boxing career as “Tommy Ryan”
• Eboli's introduction to the underworld in the 1920's and 1930's during Prohibition
• Thomas “Tommy Ryan” Eboli's career as a boxing manager and some of the fighters he managed including Tony Pellone and Rocky Castellani
• Eboli's 1952 ban from boxing due to the assault of a referee and promoter after a particularly heated bout
• Xavier's life growing up as Tommy Eboli's son and his entrance into the Marine Corps. in the early 1960's
• Xavier's chance meeting with Charles “Lucky” Luciano
• Stories from the infamous Copacobana nightclub
• Xavier's memories of notable mob figures including Vito Genovese, Vincent “The Chin” Gigante, Philip “Benny Squint” Lombardo, and others
• The circumstances of assassination of his father in 1972, the false Carlo Gambino drug rumor, and the aftermath
• We also touch on his uncle, Pasquale “Patsy Ryan” Eboli, their relationship, and his connections to the restaurant scene from The Godfather
• His uncle Pat's demotion and disappearance in 1976
• The last chilling conversation Xavier had with Vincent “The Chin” Gigante
• We cover Xavier's long life and career after the murders of his father and uncle
• We talk about his book, “Boss in the Shadows: The Life and Death of Thomas ‘Tommy Ryan’ Eboli”

Buy Xavier's book on Amazon: https://www.amazon.com/Boss-Shadows-Death-Thomas-Tommy/dp/B0DQM34JDM

We talk with Nicholas "Nick" Parisi, award-winning author and Springfield, Massachusetts mob expert.

Nick has written two books on the Springfield mob including:

1. City of Betrayal: The Genovese Family's Springfield Crew
2. Mafia Confession: King of Bootleggers Murder

Why should you trust Nick?

First, Nick is the grandson of a man named Giuseppe "Joseph" Parisi, who was deeply involved in one of the most infamous events that became a cornerstone of how the Springfield Mafia came to be

Second, Nick grew up around the mob in West Springfield, Massachusetts. He was childhood friends with notable figures such as Ty and Freddy Geas, Anthony "Bingy" Arillotta, and others.

He is widely considered to be a local subject matter expert when it comes to the Springfield mob.

100 Years of Springfield mob history

This episode covers over a century of mob history in Springfield including the early formation of the mob and the eventual alignment with the Genovese Crime Family in New York.

• How immigration in the early 1900's led to a rise in Springfield's Italian population
• The rise of Italian street gangs and the Black Hand
• The rise of the city's first boss, Carlo Siniscalchi
• The rise of Nick's grandfather, Joseph Parisi
• The eventual dispute between Siniscalchi and Parisi that ultimately led to Carlo Siniscalchi's assassination at the hands of Nick's grandfather
• The murder trial of Joseph Parisi
• The rise and untimely demise of Antonio Miranda, successor to Siniscalchi and brother of Genovese legend Mike Miranda, and the alignment with the Genovese Crime Family (which still exists today)
• The subsequent rise and assassinations of Pasqualina (Albano Siniscalchi) Miranda as well as Michael Fiore

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We then cover the golden era of the Springfield mob between the 1930's into the 1990's:

• The four decade long career of Salvatore "Big Nose Sam" Cufari, long-time boss of Springfield and Capo within the Genovese Crime Family
• Cufari's successor, Francesco "Frankie Skyball" Scibelli in the 1980's and early 1990's as Springfield's boss and Capo
• Scibelli's successor, Adolfo "Big Al" Bruno in the 1990's as the new boss of Springfield

We then shift gears to cover the rise of a new generation of Springfield mobsters, who would ultimately be responsible for the downfall of the Springfield Mafia:

• The rise of the "Young Turks" including Anthony "Bingy" Arillotta, Ty and Freddy Geas, as well as Emilio Fusco
• The coup against Adolfo "Big Al" Bruno that ultimately led to his assassination in 2003
• The rise of Anthony Arillotta as Springfield's boss and Genovese Crime Family Capo after the death of Al Bruno
• The downfall of the Springfield mob after several key players decide to testify including Frankie Roche (Bruno's assassin), Felix Tranghese (long-time Springfield made member), and John Bologna (New York mobster and right-hand man to Artie Nigro, Acting Boss of the Genovese Crime Family)
• The ultimate decision by Anthony Arillotta to flip and the men cooperated against including Ty and Freddy Geas, Arthur "Artie" Nigro, and others.

We close the episode by discussing:

• The book writing and publishing process
• The 2018 murder of James "Whitey" Bulger by Nick's childhood friend, Freddy Geas
• Nick's perspective on making judgements about government cooperators

This was an epic discussion that I hope you enjoy and share! If you want more exclusive content like this, please sign up for my Patreon channel at https://www.patreon.com/GanglandHistoryPodcast

In this episode, we talk with Ray Franze author of ‘The Heights.’

The Heights is a historical mob fiction novel based upon the early days a very real and powerful crew of Italians in Chicago Heights, Illinois that became one of the most powerful, but least well-known, crews in the Chicago Outfit (as well as nationally).

Fox News Chicago has called The Heights “A masterful dive into mob history.”

• Buy the book: https://www.amazon.com/Heights-Ray-Franze/dp/1955058083
• Blue Handle Publishing: https://www.bluehandlepublishing.com/ray-franze
• Connect on Facebook: https://www.facebook.com/theheightsnovel/
• Connect on TikTok: https://www.tiktok.com/@writerrayfranze

Here is a brief synopsis of the book:

“FALL IN LINE, OR FALL IN A GRAVE

After 30 years of research and scouring 5,000 pages of FBI files, The Heights was born. Inspired by true events and racketeers who ruthlessly fought their way into Al Capone's inner circle and expanded organized crime across the American West.

It's hard to believe Sal Liparello has survived long enough to enjoy a midday scotch on his California tomato farm.

The sixty-something crime boss from Chicago Heights helped take out Sicilian gangs, advised Al Capone on some of his biggest moves, and rubbed elbows with the Kennedys, Sinatra, and Marilyn Monroe - all while avoiding the likes of Eliot Ness and J. Edgar Hoover.

But as he surveys the fruits of his labor, Sal also remembers the cost of staying above ground and out of prison.

And all those decisions are about to catch up with him.”

In the episode, we dive deep into the book and talk about:

• The characters and their backgrounds
• The process of mixing real history within a fictional novel following a single character
• The question of historical fiction versus non-fiction writing
• The writing process and getting published
• Weaving in real characters such as Al Capone, Tony Accardo, and even Eliot Ness

Additionally, we dig deep into the real history behind ‘The Heights’ to discuss the real-life counterparts of some of the characters within the books. We discuss the origins of the Chicago Heights crew and how they eventually joined forces with Al Capone to become a part of the larger Chicago Outfit in the 1920's and beyond.

We also discuss their exploits and their potential part in planning the St. Valentine's Day Massacre. Mentioned in this episode are:

• Francesco Lipperatti (also known by the name “Frank LaPorte”)
• Vincenzo Ameratti (also known by the name “Jimmy Emery”)
• Dominico Roberto (also known by the name “Dominic Roberto”)

These three men were the core leaders of the Chicago Heights crew in the 1920's that murdered their way to the top of Chicago Heights, formed partnerships with Al Capone and eventually were brought into the Chicago Outfit under Capone. They ran bootlegging in what Eliot Ness dubbed “the second wettest city in America” behind Cicero, Illinois, and provided shooters and brains whenever Capone needed them.

These three men ran Chicago Heights for the Outfit from the 1920's into the early 1970's before the crew was taken over by younger (and more violent) elements of the family. Yet, their history and relative importance in the national crime syndicate is relatively unknown.

Additional source: https://www.myalcaponemuseum.com/id193.htm