In this episode of the podcast, I’m joined by author Ron K. Fried for a deep dive into one of the most compelling figures in organized crime history: Frank Costello, the mob boss who rose to power during Prohibition and later became known as the “Prime Minister of the Underworld.” We discuss Ron’s novel Frank Costello: A Novel—a carefully researched work of historical fiction that vividly brings Costello’s complex character to life. Together, we explore the real-life events behind the book and how Ron approached writing about a man who straddled the worlds of organized crime and political power.

We start with Costello’s early years—his immigration from Sicily, his upbringing in East Harlem, and how he gravitated toward petty crime and gang life. In this environment, he met future legends like Charles “Lucky” Luciano, Meyer Lansky, Benjamin “Bugsy” Siegel, and Vito Genovese—key figures in the creation of a national crime syndicate.

During Prohibition, Costello built his fortune and reputation through bootlegging, running extensive liquor operations, and leveraging alliances that would shape the mob’s future. We discuss the bloody 1931 power shift following the assassinations of Joe Masseria and Salvatore Maranzano, which led to the formation of the Five Families. As Luciano’s trusted associate, Costello rose in the ranks of what would become the Genovese Crime Family.

We explore the mid-1930s transition period when Luciano was imprisoned and Genovese fled to Italy to avoid a murder charge. This opened the door for Costello to become acting boss, a position he would hold for nearly 20 years. During this time, he built a reputation as a refined, politically connected mobster who favored influence over brute force—garnering real sway in political and judicial circles.

We delve into Costello’s political entanglements, including the wiretap involving Judge Thomas Aurelio, in which Costello was caught influencing judicial appointments. We also examine his ties to New York Mayor William O’Dwyer and his suspected involvement in the mysterious death of Abe Reles, a Murder, Inc. informant who “fell” from a window while under police protection.

One major focus is Costello’s appearance at the 1951 Kefauver Committee hearings, a turning point in his career. His decision to only allow his hands to be filmed became a media sensation and diminished his power and mystique. The public scrutiny weakened his position and empowered rivals—most notably, Vito Genovese, who sought to reclaim the top spot in the family.

We look at the 1957 assassination attempt on Costello, carried out by Vincent “The Chin” Gigante on Genovese’s orders. Though Costello survived, he chose to step down. We also discuss the murder of Albert Anastasia later that year, and the theory that Costello may have had a hand in framing Genovese, leading to his 1959 conviction on narcotics charges.

From there, we examine Costello’s final years, during which he remained influential behind the scenes but largely retired from active leadership. We reflect on his complex legacy: a ruthless gangster who carefully curated an image of legitimacy and respectability. Ron shares how he explored that duality in his novel—bringing humanity to a man who lived in both the criminal underworld and the corridors of political power.

We also discuss mob portrayals in film and television, and look ahead to the upcoming 2025 gangster film Alto Knights, a much-anticipated movie featuring dramatizations of several key historical figures we covered. Our conversation touches on why the Mafia continues to fascinate the public and how Frank Costello’s story stands apart as one of strategy, survival, and power.

📘 Check out Ron K. Fried’s book Frank Costello: A Novel – available wherever books are sold. https://www.amazon.com/Frank-Costello-Excelsior-Editions-Ronald/dp/143849114X

In late August 1979, the FBI's Brooklyn-Queens Metropolitan Resident Agency (the BQ) received a significant tip from a top-echelon informant within the Genovese crime family. This informant, known as "Bob," reported that Paul Castellano, head of the Gambino crime family, had mentioned an upcoming major meeting at Gurney's Inn in Montauk, New York. The anticipated attendees included prominent figures such as Frank "Funzi" Tieri of the Genovese family, Carmine "The Snake" Persico of the Colombo family, and Tampa's organized crime leader, Santo Trafficante Jr.

Recognizing the potential significance of this gathering—the most consequential since the 1957 Apalachin summit—the FBI swiftly mobilized. Agents, including undercover operatives, were dispatched to Gurney's Inn, posing as tourists to monitor arrivals and activities. Specialized personnel were prepared to install surveillance equipment to capture conversations during the meeting.

Despite the extensive preparations, the anticipated meeting never occurred. The reasons remain uncertain; possibilities include the informant providing inaccurate information, the mobsters altering their plans, or suspicions about increased surveillance leading to a change in venue. This outcome was reminiscent of the 1957 Apalachin meeting, where law enforcement's unexpected presence led to the mobsters' dispersal.

While the immediate operation at Gurney's Inn did not yield the expected results, it underscored the FBI's evolving strategies in combating organized crime. The bureau's readiness to deploy advanced surveillance techniques and coordinate large-scale operations marked a shift towards more proactive and sophisticated approaches. This evolution contributed to significant successes in subsequent years, including the Mafia Commission Trial of 1986 and the conviction of John Gotti in 1992. This episode about the FBI’s almost-successful attempt to bug a major mob meeting at Gurney's Inn illustrates the challenges law enforcement faced in infiltrating organized crime and highlights the pivotal role such operations played in modernizing the FBI's methodologies.

Joining us in this episode, we have:

Daniel Edward Rosen, a staff reporter from the New York Sun, whose work has appeared in Esquire, the New York Observer, City Journal, New York Magazine, and the New York Times.

See his original article: https://www.nysun.com/article/how-the-fbis-mad-dash-to-wiretap-the-mob-at-a-montauk-hotel-nearly-50-years-ago-helped-modernize-todays-agency

Frank DiMatteo joins us to provide color commentary based upon his experiences growing up embedded in one of the most infamous mob crews in the history of the American Cosa Nostra.

Frank is the son of Ricky DiMatteo, a member of the legendary Gallo Crew of the Colombo Crime Family in New York City. He is also an author of several books in his own right including Growing Up Mafia, Mafia Hit Man, Lord High Executioner, The Cigar, Carmine the Snake, Red Hook, as well as the publisher of Mob Candy.

In today's episode, we wrap up one of the most detailed and historically rich series we’ve ever done. In Part Three of our special deep dive into the FBI’s 1967 report on La Cosa Nostra, we close the book on an era where the mob’s influence was at its peak across the United States.This final installment takes us beyond New York’s Five Families and paints a broader picture of organized crime’s national footprint — from the power struggles within familiar crime families to lesser-known but highly active Mafia outposts across the country.Read the full FBI report for yourself: https://www.maryferrell.org/showDoc.html?docId=113324🧠 In This Episode, We Cover:✅ The Bonanno Crime Family’s descent into chaos, civil war, and betrayal — as Joe Bonanno returns to face down the Commission and fight to reclaim his throne.✅ The Gambino Family’s rise, as Carlo Gambino cements his control and grooms Paul Castellano behind the scenes — a critical step in Mafia succession history.✅ The Genovese Family’s murky leadership, with Vito Genovese in prison and shadow bosses like Philip “Benny Squint” Lombardo running the show unnoticed.✅ The Lucchese Family’s transitional moment following Tommy Lucchese’s death — and the jockeying between Carmine Tramunti and Tony “Ducks” Corallo to take control.✅ The Colombo Family’s quiet power, with key figures like Sonny Franzese and Carmine Persico taking shape as future legends.But that’s just the beginning.🗺️ We also dive into the overlooked regional strongholds that reveal just how deep and wide La Cosa Nostra’s reach really was:Buffalo, NY – Under Stefano Magaddino, this powerful family controlled Western New York and stretched its reach into Canada and several upstate cities.Albany / Utica / Syracuse, NY – Subordinate to Buffalo, these cities were managed by men like the Falcone brothers and Anthony DeStefano, with FBI confusion over whether Utica operated as its own borgata.Cleveland, OH – Led by John Scalish with key figures like Frank Milano and James Licavoli, the Cleveland family maintained quiet power and deep national connections.Baltimore, MD – Frank Corbi ran a small but respected Gambino-aligned crew while the Jewish mob held most of the city’s gambling rackets.Rockford, IL – Uniquely independent, the Rockford family under Joseph Zammuto resisted Chicago Outfit control and operated with its own leadership structure.Dallas, TX – Joe Civello led a low-profile family that may have answered to the Genovese Family rather than New Orleans, challenging traditional narratives.Denver, CO – Though unnamed in this report, the Smaldone brothers dominated organized crime in Colorado, running a tightly knit and durable operation.Boston & Providence – Raymond Patriarca controlled New England, but the FBI misread key leadership roles, as Gennaro Angiulo and Henry Tameleo held more power than noted.🎯Each of these regional snapshots is more than just a list of names — they offer a rare “moment-in-time” look at how the FBI viewed organized crime in 1967. Some of it is accurate, some speculative, and some flat-out wrong — but all of it is fascinating.The report lists:📋 Full leadership rosters for major New York City families: Gambino, Genovese, Lucchese, Colombo, Bonanno.🌍 Regional family structures in other cities: Buffalo, Cleveland, Chicago, Dallas, Rockford, Baltimore, Denver, and many more.⚖️ Acting titles, rival factions, and transitional leadership: Families undergoing internal strife (e.g., Bonanno and Chicago).In fact, we cover 30+ cities and over 200 individual mobsters across the United States, so get ready to dig in.🎬 Catch Up On Parts One & Two:Part One: https://youtu.be/p3YTUNRnDlwPart Two: https://youtu.be/hzz1F6E5c7A🔔 Support the show on Patreon:https://www.patreon.com/GanglandHistoryPodcast

In Part Two of our deep-dive biography on Paul "The Waiter" Ricca, we chronicle his ascent to the top of the Chicago Outfit from the late 1940s through the early 1970s — a reign that cemented his legacy as one of the most powerful and influential mob bosses in American history.

Listen to Part One: https://youtu.be/D2S-22pslCA

This episode picks up with Ricca serving time in Atlanta Federal Penitentiary following his conviction in the infamous Hollywood extortion case — a racket that siphoned millions from the motion picture industry during the 1930s and 1940s. We explore Ricca's brutal prison experience under Warden Joseph Sanford, a notorious white supremacist who cracked down on Italian inmates, and how Ricca's allies on the outside — including Tony Accardo and Murray "The Camel" Humphreys — pulled political strings and greased palms to orchestrate his early transfer to Leavenworth and eventual release after serving only three years.

Once back in Chicago, Ricca quietly shared power with Tony Accardo in one of the most successful power-sharing arrangements in Mafia history. While Accardo handled day-to-day operations, Ricca became the Outfit's elder statesman — making high-level decisions, approving hits, and shaping the organization's future from behind the scenes. The two men orchestrated the Outfit's expansion into Las Vegas, using Teamsters pension loans and alliances with Meyer Lansky to finance casinos like The Stardust, Desert Inn, and Riviera — creating a multimillion-dollar pipeline of skimmed cash that flowed directly into Chicago's coffers for decades.

Despite his low profile, Ricca remained a prime target for law enforcement. Throughout the 1950s and 1960s, he fought off tax evasion charges, perjury indictments, and a relentless deportation campaign that sought to return him to Italy — where he had been convicted of two murders in his youth. His decade-long legal battle to avoid deportation became one of the longest-running immigration cases in American history, with Ricca outmaneuvering authorities at every turn.

As law enforcement pressure mounted, Ricca and Accardo made the strategic decision to promote Sam "Momo" Giancana as front boss of the Chicago Outfit in the mid-1950s — allowing the brash and flashy Giancana to become the lightning rod for law enforcement while Ricca and Accardo continued pulling the strings from the shadows. But Giancana's high-profile lifestyle, affairs with celebrities, and erratic leadership style caused turmoil within the Outfit. By the mid-1960s, Ricca and Accardo had seen enough, orchestrating Giancana's ouster and restoring order to the organization.

During this era, Ricca rubbed shoulders with and mentored some of the Outfit's most notorious figures, including Murray Humphreys, Gus Alex, Ralph Pierce, Sam Battaglia, Willie Daddano, and Felix "Milwaukee Phil" Alderisio. He also played a pivotal role in grooming the next generation of Chicago gangsters — including the fearsome enforcer Marshall Caifano and the psychopathic loan shark Sam "Mad Sam" DeStefano.

Even into his 70s, Ricca's influence never waned. He remained the ultimate consigliere of the Chicago Outfit — a man whose word was law and whose wisdom guided the Outfit's rackets from Chicago to Las Vegas. This episode breaks down how Ricca's strategic brilliance, political connections, and ruthless pragmatism helped him outlast nearly all of his contemporaries and solidified his place as one of the most underrated and powerful mobsters in American history.0

• 0:00:00 Start
• 00:00:42 Opening Remarks
• 00:01:37 Cliff-Notes of Part One
• 00:07:24 The Waiter's Time in Prison (Mid-to-Late 1940's)
• 00:28:15 Co-Boss of The Outfit (Late 1940's and 1950's)
• 01:17:20 Running the Chicago Outfit (Keeping Control in the 1960's)
• 02:13:56 Late Career & Legacy (The 1970's)02:23:16 Closing Remarks

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.

***

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:

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.

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

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:

We close the episode by discussing:

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.”

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:

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:

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

In this episode, we continue the “State of the Mafia (1967)” series. If you haven’t already, I highly encourage you to go back and watch ‘The State of the Mafia: Part One’ “The rules that hold us together” as it will be a very good primer for this episode’s content.

I’m calling this show ‘The State of the Mafia (1967): Part Two’ “Life or Death Obligations.” Like the first part of this series, this report will jump around a lot, but in the end I think you’ll still enjoy it, and hopefully it teaches you “a couple of three things.”

Okay, so let’s reset the stage here. 

This 1967 FBI report, which we began to cover in Part One (again, go watch or listen to it first if you haven’t), is a veritable gold-mine of information. The aim at the time of creation was focused on providing an overall picture of LCN membership and activities throughout the United States as things stood in 1967. The report was declassified in 1996.

The originator of the report was a man named Robert G. O’Neil, and the report itself was submitted to the FBI Director at the time, one J. Edgar Hoover.

Sometimes in the course of historical research, you just find things that are simply too good not to share. In this case, I found this report by accident, got to reading it, and was very much enthralled by it. And based on the responses in the first episode (a 96% approval rating on YouTube), I think it’s worth continuing. 

In Part One, I covered the following topics:

In this episode, we’re going to continue along that track and get into:

For the sake of time, we’ll stop this episode after transfers of members.

The report in its entirety will likely require four parts in total to fully cover, and will be linked in the description of the episode. Again, it contains references to 50+ cities and 196 informants in total. So, it’s a massive dossier and treasure trove of information on the Mafia.

Link to full report: https://www.maryferrell.org/showDoc.html?docId=113324#relPageId=21

There are many different families, individual mobsters, and stories referenced in this episode. The episode bounces from the "who's who" of the American Mafia, to several lesser known characters, citing informant reports that were geared on teaching the FBI about the Mafia back in the 1960's.

And now, I'm bringing this information to your doorstep.

We talk with Giovanni Rocco, a former deep cover agent for the FBI, is responsible for taking down the American Mob organization commonly referred to by the media as “The Real Sopranos.”

During Operation Charlie Horse, Giovanni infiltrated the DeCavalcante crime family based in New Jersey and personally gathered enough evidence to prosecute and convict several high-ranking members and associates of the crime family. This action, while bolstering his legend in the undercover world, ultimately led to early retirement and the relocation of his family. 

During his decades-long career as an undercover for the federal government, he successfully infiltrated outlaw motorcycle gangs, domestic and international terror organizations and the Mafia. Drawing from his service in law enforcement in various positions, Giovanni now shares his expertise with law enforcement, military and intelligence units worldwide.

More recently, he has become the host of the show, “Inside the Life” along with co-host Dutch McAlpin, produced by The Mob Museum, where they give listeners a one-of-a-kind look into the inner world of organized crime, featuring guests who have lived on both sides of the law.

In addition to his work as a subject matter expert and host of a successful YouTube show, Giovanni is also an author. He released his autobiography entitled, “Giovanni’s Ring: My Life Inside the Real Sopranos” released in February of 2021. I’ll leave the link in the description of the episode, and if you’d like, you can get a signed copy from Giovanni himself. Definitely a must have book for your collection.

Giovanni’s experiences have been featured in The Washington Times, the New York Post, and more. 

This is his story in his own words.

Episode chapters and timestamps:

00:00 Start

01:27 Opening Remarks

03:36 Interview Begins

04:38 Growing up in Bayonne, New Jersey

06:40 Influence of the Mafia in Bayonne

08:32 Giovanni's family and upbringing

12:09 The influence of violence and the draw of the streets

16:03 Going from "Black Sheep" to becoming a police officer

18:28 The importance of the law enforcement oath

21:06 Giovanni's early law enforcement career

24:09 Working in extremely violent areas of New Jersey

27:35 Dealing with fear on the job

29:56 Were neighborhoods safer when the mob was in control?

31:47 Becoming an undercover operative

33:26 Undercover work and the element of truth

37:10 Physical tells and how they may betray an undercover operative

39:38 Balancing relationships and family life with undercover work

45:55 Introducing Giovanni Gatto (the alter ego)

48:50 The art of evasiveness

50:45 'Operation Charlie Horse' begins

55:19 Meeting Luigi 'Lui the Dog' Oliveri, alleged made member of the DeCavalcante Crime Family

55:52 Getting an introduction to Charlie 'The Hat' Stango, Capo in the DeCavalcante Crime Family

57:08 Getting to know Charlie 'The Hat' Stango

59:06 How 'Operation Charlie Horse' progressed

01:00:00 The Mafia's approach to vetting Giovanni

01:04:35 Walking the legal line as an undercover

01:06:09 Facing dangerous situations as an undercover

01:08:20 Nearly getting caught by The DeCav's

01:13:10 Nearly getting caught, the infamous bridge story

01:16: 15 Nearly getting caught, the soccer game

01:17:12 The end of 'Operation Charlie Horse'

01:18:41 Giovanni gets a contract to kill

01:20:40 The leadership of the DeCavalcante Family during Giovanni's undercover work

01:21:58 The possibility of faking a 'hit'

01:24:40 Early retirement and beginning work with training and development for law enforcement and military personnel

01:32:45 Doing the 'Inside the Life' podcast for The Mob Museum

01:39:25 Closing remarks

In this episode, special guest Tony Taouk and myself discuss the career of infamous Philadelphia mob lawyer, Robert "Bobby" Simone (1933 - 2007).

Robert F. Simone was known for winning a string of difficult cases for clients that included members of Philadelphia's organized-crime family such as Nicodemo "Little Nicky" Scarfo, Philip "Crazy" Phil Leonetti, Frank "The Baracuda" Sindone, union boss John McCullough, and many more.

We discuss many topics surrounding the life and times of Simone including:

Link to Simone's book, "The Last Mouthpiece: The Man Who Dared to Defend the Mob" https://www.amazon.com/Last-Mouthpiece-Man-Dared-Defend/dp/0940159694

Link to "MOUTHPIECE: VOICE FOR THE ACCUSED" (2002)" * PRODUCED BY THE HISTORY CHANNEL (Used in this video) https://www.youtube.com/watch?v=v7hDUNfyRJc