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