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The ‘Fear City: New York vs. the Mafia’ Syllabus

A list of books, movies, shows, and forums to check out after you’ve delved into Netflix’s new documentary on the mob

Getty Images/Ringer illustration

The most intriguing figure in Fear City: New York vs. the Mafia, the new Netflix documentary about the largest federal investigation into the mob in U.S. history, isn’t Paul Castellano, the so-called white-collar don who ran the Gambino crime family like a Fortune 500 company. It’s not John Gotti, the flashy boss who would later order the hit on Castellano and become a tabloid sensation in the 1980s. Nor is it Rudy Giuliani, then a young U.S. attorney who oversaw the convictions of the heads of the Family Families of New York. It’s not the capos and soldiers who give on-camera interviews. It’s not Curtis Sliwa, who founded the Guardian Angels to combat street violence in his home city.

The most interesting person in Fear City is a man with a leather bag and a penchant for disguise.

Introduced just over halfway through the first of the documentary’s three parts, Joe Cantamessa was an agent on the FBI’s special operations squad with a knack for planting concealed microphones and getting through locked doors. And unlike other agents featured in the film, his appearance—in the early ’80s, he sported aviator sunglasses and a lush, shaggy mane—and the demeanor he developed as a self-proclaimed “bad kid growing up” helped him do his job without getting noticed. Given that he’s bugging the homes of the most powerful mobsters in the five boroughs, that’s essential. We first meet Cantamessa, who prefers the title of “Black Bag Man,” as he’s looking for a way to drop a wire in the home of Angelo Ruggiero, a Gambino family captain who “ate a great deal and talked a great deal” and seemed like the best starting point for a federal investigation. To do so, Cantamessa waits for a legitimate phone problem at Ruggiero’s house, calls off the phone company, enters the home, and puts a tap on the mobster’s line—all while an unsuspecting associate of Ruggiero watches. Later, Cantamessa is able to implant a recording device in Castellano’s Staten Island home by interfering with the boss’s TV signal, and then showing up as a representative from the cable company. It’s a genius plan that would pay dividends that were both salacious and key to building a case.

But in Fear City, Cantamessa’s stories are told with the humor and suspense typically reserved for mobsters telling their stories. “My blending technique would depend on the neighborhood, and generally speaking, I’m just a local guy doing his job,” he says with a smirk.

The decision to focus on the likes of Cantamessa, other investigators, and the young prosecutors who would end the glory days of the New York mafia is what sets Fear City apart from other organized-crime movies and documentaries. The movie shows flashes of the lifestyle that’s been glamourized throughout media—an early montage talks about cocaine-pushing, disco-era mafiosos wearing polyester waffle-weave bell bottoms and lilac water cologne—and interviews with mob associates John Alite and Michael Franzese help push the story forward. But Fear City askews any glorified retellings of those stories, instead opting for a seldom-seen perspective. That’s by design, says Jon Liebman, one of the film’s executive producers and a former prosecutor who joined the New York U.S. attorney’s office shortly after the events covered in the documentary, commonly referred to as “the Commission case.”

“To tell the story of the Commission case, you needed to tell the story of how it was put together, which was a collective effort on the part of the FBI and the U.S. attorney’s office in New York, to conceptualize the fight and also to investigate it and prosecute it,” Liebman says.

What makes Fear City compelling isn’t just the cat-and-mouse game told from a new vantage point, however. It’s a story about two dramatically changing institutions at crossroads: the city of New York, which had developed a reputation for street violence in the 1970s and was set to undergo a construction boom that would transform its physical and financial landscapes forever; and the FBI, which had struggled to build a case against the mob bosses who insulated themselves from culpability. The mafia would find a way to insert itself into the skyscraper development via the concrete industry. The FBI and U.S. attorney’s office, meanwhile, would figure out how to prosecute the heads of the Five Families via the Racketeer Influenced and Corrupt Organizations Act, commonly referred to as RICO. Eventually, the billions of dollars the mob pulled in from the construction jobs would become a key piece of evidence in the Commission case, the RICO trial at the center of Fear City that took aim at the heads of the Bonanno, Colombo, Gambino, Genovese, and Lucchese families.

“The notion of attacking the top leadership was the most significant contribution from a prosecutorial perspective,” Liebman says. “Instead of arresting and prosecuting lower level people, who were out in the street committing crimes, this case was about going after the bosses. And the message to the entire mafia is if you can get the bosses, you can get anyone. They were not untouchable.”

If Fear City has a star beyond the Black Bag Man, it’s director Sam Hobkinson, who captures the grit of ’70s and ’80s New York without sacrificing the highly stylized sheen that makes so many Netflix true-crime docs pop. Drawing on unprecedented access to surveillance tapes and photos, Hobkinson reveals key info through fragments of conversations between the mobsters and reenactments that manage to enhance the story, rather than detract from it. This pulls the viewer in, making them bear witness to the growing mountain of evidence against the bosses and the dramatically expanding scope of the investigation without bogging them down in legalese. “I hope people enjoy the ride but also understand the complexity and daring of putting these cases together,” Liebman says. “I hope people can appreciate the complexity and daring of the people involved.”

So what do you need to consume before (or after) Fear City? The Ringer has put together a syllabus to help guide you through the documentary, the peak of the New York mob, and beyond.

The Conversation

The Godfather lords over the mafia genre like don does his capos. But in the case of Fear City, Hobkinson says another 1970s Francis Ford Coppola classic served as a touchstone: The Conversation, which tells the story of a surveillance expert wrestling with the effects of his job. Gene Hackman stars as “the best bugger on the West Coast,” Harry Caul, who’s contracted to record a conversation between a young couple in a San Francisco park. It soon becomes clear that the contents of his tapes could put people’s lives in danger. Caul, who had previously maintained distance from his work, becomes involved in the case, ultimately uncovering a truth that threatens to destroy him. Now 46 years old, The Conversation remains a thrilling character study whose message has far outlived much of the technology featured in it. It’s also still a technical marvel, from the opening telephoto shot to the virtuosic sound mixing. Its influence on Fear City shines through most during an early scene in which Harry edits tape, revealing a new layer to the couple’s discussion with each playback—just as the endless loop of wiseguy tapes help bring the case against the Commission into focus.

Baby Huey and the Baby Sitters, “Hard Times”

“Hard Times,” which serves as the opening theme for Fear City, has been a grail for hip-hop producers for decades. One need not look past its opening four bars, with pounding drums and an ominous bass line, to see why it’s been sampled by the likes of A Tribe Called Quest, Ghostface Killah, and The Game. But even without those interpretations, “Hard Times” stands on its own as a forgotten psych-soul classic—though one that comes with a tragic backstory. James Ramsey, an Indiana-born singer who recorded under the name Baby Huey, was discovered in 1969 after performing for Donny Hathaway and Curtis Mayfield. The latter signed Ramsey and his band to his Curtom label, and over the next year wrote and produced the songs that would comprise the debut Baby Huey album. “Hard Times” is the standout, but the pulsating fuzz of “Running” and gritty covers of “California Dreamin’” and “Mighty Mighty” are also must-listens. Unfortunately, Ramsey wouldn’t live to see the songs’ release: By late 1970, his weight had eclipsed 400 pounds and he’d developed an addiction to heroin. On October 28 of that year, he was found dead in a Chicago motel room at age 26. In 1971, Curtom released The Baby Huey Story: The Living Legend. Nearly five decades later, the album and “Hard Times” are still finding acolytes.

Don’t Fuck With Cats: Hunting an Internet Killer

The producers of Fear City had a breakout Netflix hit late last year centered on a totally different kind of investigative documentary. The three-part Don’t Fuck With Cats focuses on a small group of private citizens who stumble across a video of a depraved person killing kittens and search for truth. What follows is a grim tale that involves internet sleuthing and the murder of a Chinese international student studying in Toronto. Underneath those stories, however, Don’t Fuck With Cats explores our relationship with social media, celebrity lust, and the hunt for justice. It’s a deeply unsettling watch, but a must-see for true-crime fans and anyone fascinated by the power determined individuals can wield.

Giuliani Time

Fear City ends with a brief clip of Rudy Giuliani winning the 1993 mayoral election in New York, buoyed in part by his work on the Commission case. He would help usher in a new era for the city—one more cosmopolitan, glossy, and corporate than the decades that preceded it. His two terms were not exactly idyllic, however: From the “broken-windows theory” style of policing he supported to the defunding of the public school systems to a litany of civil lawsuits filed against his administration, his policies did not benefit all New Yorkers. The 2006 documentary Giuliani Time explores the more fraught side of his time in office, including the 1999 killing of Guinean immigrant Amadou Diallo by plain-clothes cops and a 1997 incident in which NYPD officers brutalized and sexually assaulted a Haitian man named Abner Louima. (The documentary gets its name from Louima’s claim that the officers shouted the phrase shortly before he was attacked; Louima recanted that part of the story, though the assault on him was very real.) While Giuliani Time feels unfocused in parts, it’s a crucial look at the man who was once dubbed “America’s Mayor,” as well as the city he ran.

Five Families: The Ride, Decline, and Resurgence of America’s Most Powerful Mafia Empires, Selwyn Raab

By virtue of focusing on the investigators and prosecutors, Fear City doesn’t provide much background of the lives of the mafia figures at the center of the investigation. For completists, there’s Selwyn Raab’s 2005 book exploring the history of organized crime in America, the mob families targeted in the Commission case, and how the mob has transformed since the mid-1980s. It’s long—the 10th anniversary edition is nearly 800 pages—but it’s a rigorously reported and researched text that avoids the conspiracy-heavy approach of so many similar books. All the big names, from Gotti to Gravano to Castellano, are represented in Five Families, but Raab also gives life to the rise and fall of the small-time criminals that surrounded them. By telling their stories, along with those of the people that helped bring down the Commission, Raab’s book is among the most complete texts on the mafia that have ever been produced.


Perhaps you don’t like your mafia history rigorously reported and researched. In that case, allow me to introduce you to an internet forum full of amateur Selwyn Raabs. GangsterBB—specifically its Organized Crime - Real Life subforum—is a place where a thread titled “Why the mob war in Montreal may be far from over” stretches on for seven years and 104 pages, and where users debate whether the current protests calling for police reform and defunding will lead to a new rise of the mafia. GangsterBB denizens also seem to have a lot of info: This thread on the Patriarca crime family from Providence, Rhode Island, has data on the mob’s local recruitment pool in the 1980s and how many making ceremonies have been held in New England in the past few decades. (“RI had one in 97 for a few guys. Whether it was recognized by all 5 families depends on who you talk to.”) Is this all just hearsay and fanfic? Who’s to say? But it’s a lot of fun for anyone looking to kill a few hours reading about the mafia. (H/t to Nick Usen, my personal guru for all things modern-mob related, for putting me on to this one.)

The Sopranos, “Mr. Ruggerio’s Neighborhood”

All of The Sopranos is required viewing, for everyone from mafia buffs to prestige TV connoisseurs to people who just want to understand the recent rash of memes. But the opening episode of Season 3 is particularly germane to Fear City. “Mr. Ruggerio’s Neighborhood” breaks from series convention and puts Tony and his family in the background, instead focusing on the FBI agents who attempt to bug his house. There’s a lot of humor packed in the hour—Tony singing “Dirty Work,” A.J. being referred to as “Little Bing” by the FBI agents, the tennis instructor that takes a special interest in Adriana—as well as a little bit of camp. (The mashup of “I’ll Be Missing You” and the Peter Gunn theme is a little too much, even in a pre–Girl Talk world.) It’s not among the series’ finest episodes, but it’s certainly unforgettable. It also connects back to Fear City on a deeper level: The “Mr. Ruggerio” in question is Tony’s plumber, who arrives after the Soprano household’s water heater explodes; in reality, it’s almost certainly a reference to Angelo Ruggiero, a reputed Gambino family associate whose house was bugged early in the investigation of the Five Families. Of course, Tony fares a little better on the surveillance front, thanks to an assist from Meadow. The key figures in the Commission case had no such luck.