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Steven Malanga
Unglamorous Mobsters
As a 1988 HBO documentary reveals, the real Sopranos were brutal—and banal.
4 April 2007

The Sopranos, the HBO series entering its final season on Sunday night, won fame by depicting a Mafia crew whose members had begun assimilating into middle-class suburban life—moving into McMansions, raising kids who attend Ivy League schools, discovering the psychiatrist’s couch (or armchair).

Interestingly, it was HBO, nearly 20 years ago, which first gave us a look at what the real mob was like when it started to go suburban—and the picture is nothing like The Sopranos. The now-forgotten Confessions of an Undercover Cop, a fascinating 1988 documentary, traced the decline and fall of the very Jersey crew that inspired The Sopranos—the crime family of Ruggerio “Richie the Boot” Boiardo, whose gang was less introspective, even more violent, and a lot less glamorous than Tony’s fictional mob.

Sopranos creator David Chase had learned about this Jersey mob as a child. Visiting relatives in Newark’s predominantly Italian-American North Ward, he met a cousin with “fuzzy connections to a prominent mob family in Livingston,” an exclusive suburb where Boiardo had moved. Though Chase says in a 2002 interview in New Jersey Monthly that “90 percent of [the show] is made up. . . . it’s patterned after this [family].”

Boiardo, known simply as the Boot around Newark, began running numbers while working as a milkman before Prohibition, and he quickly figured out that crime paid better than dairy. He moved up the racketeering ranks and during Prohibition competed with another prominent Newark mobster, Abner “Longy” Zwillman, to smuggle booze through Newark. Working independently, the pair supplied much of the eastern half of the United States. Their contending rackets got so big that, according to FBI files, Al Capone himself journeyed to Newark to settle a feud between them when it threatened to disrupt the flow of illegal booze.

There was little mystery about the Boot’s rise. Like the fictional Vito Corleone, he was brutal and had a knack for surviving. He earned his nickname from his habit of stomping his enemies to death, and he consolidated his power in Newark after withstanding a hit by a rival gang that left him full of bullets but defiantly alive. The Boot, moreover, passed his viciousness on to his son Anthony “Tony Boy” Boiardo and recruited other like-minded hoods. Not only did these guys dispose of their enemies as sadistically as anyone in The Sopranos, but rather than brood over their bad deeds as some characters in the series do, the real Sopranos actually recounted their nastiest killings with relish.

In one FBI surveillance tape, for instance, Tony Boy declares, “How about the time we hit the little Jew.” An associate adds, “As little as they are, they struggle.” Then Tony Boy finishes describing the scene: “The Boot hit him with a hammer. The guy goes down and he comes up. So I got a crowbar this big. . . . Eight shots in the head. What do you think he finally did to me? He spit at me.” In another tape, the mobsters recall with equal delight locking a victim in a car trunk and setting it afire. “He must have burned like a bastard,” one mobster says.

As in The Sopranos, the Boot joined the flight of Italian Americans out of Newark to the Essex County suburbs, where he built an opulent walled-in retreat in Livingston. But unlike Tony Soprano’s modern McMansion, the Boot’s estate was more like some European fortress, described by Life as “Transylvanian traditional” in its architectural style, with busts of famous Romans dotting its grounds. Another particularly noteworthy feature: a large furnace, rumored to be where the Boot’s crew disposed of his enemies’ remains.

By the time Confessions takes up this gang’s story in the mid-1980s, Boiardo had recently died, as, unexpectedly of a heart attack, had his son and heir apparent, Tony Boy, leaving what remained of the crew to their lieutenants. Most of these hoodlums had also by now decamped to Newark’s suburbs—places like North Caldwell, Roseland, and Bellville, all mentioned frequently in The Sopranos. But unlike Tony’s crew, the real Sopranos still used Newark’s decidedly unglamorous and gritty North Ward as their base of operations.

The investigation at the center of Confessions begins by chance, when a retired East Orange, New Jersey cop named Mike Russell is driving down Bloomfield Avenue in North Newark and sees two young guys attacking an older one. Russell goes to the aid of the older man, driving off the attackers. He discovers that the guy he’s helped is Andrew “Andy” Gerardo, now head of Boiardo’s old gang. Gerardo invites Russell into his hangout, a coffee shop on the avenue just a few steps from a monument to Christopher Columbus and the Italian American contribution to America. There, Russell meets other key members of the crew, who treat him like a hero and befriend him.

Russell then contacts a friend in the state police, who asks him to begin surveillance on the crew. Incredibly, the mobsters invite Russell to move his oil delivery business into a storefront adjoining their Newark headquarters, figuring he’s friendly, and from there the investigation takes off. But unbeknownst to the state police, Russell enlists a cameraman and begins his own videotaping of the Jersey crew, which provides most of the material for the HBO documentary.

The footage illustrates the gap between Hollywood and mobster reality. Like most celluloid gangsters, Tony Soprano’s crew carries itself with a certain “mob chic,” evident in everything from Silvio’s elaborately coiffed jet-black mane to Paulie’s meticulously delineated grey sideburns to the expensive Italian suits that Tony and the boys favor. Their headquarters is the baby boomer’s fantasy of bad-boy living, the Bada Bing strip club.

But the real-life evil is more banal. The Boot made his headquarters inside a candy shop on Roseville Avenue in North Newark, transformed by the time of Confessions into a rinky-dink pizzeria and dimly lit adjoining cocktail lounge called The Finish Line. One look inside The Finish Line and it’s clear that for this real mob crew, style took a back seat to earning money.

Most of the action that Russell investigates takes place in even less glamorous social clubs around North Newark—little more than storefronts sporting linoleum floors, faux wood paneling, folding chairs, and card tables. From these motley locations, which could be had cheaply in Newark once rising crime and white flight eroded the city’s retail base, the crew ran nightly card games that netted them about $1 million a week. The earnings were big, though these games were nothing like those in The Sopranos, where mob-run gambling sessions take place in hotel suites and occasionally feature big name “guest” players like Lawrence Taylor.

Confessions makes it clear that few real mobsters could ever score a bit part on The Sopranos or any other gangster show—they simply look too ordinary. The Confessions crew runs around North Newark in Bermuda shorts, white tee-shirts, and knee-high socks, or in cheap polyester slacks and Ban Lon shirts—a look that would never get you a photo shoot in Vanity Fair or on the cover of Cigar Aficionado, where James Gandolfini, who plays Tony Soprano, has appeared.

The investigation recounted in Confessions resulted in 48 indictments and more than 30 convictions or guilty pleas for gambling, loan sharking, and racketeering, which effectively broke the back of the Genovese family in Jersey. At the end of Confessions we see the crew making a “perp” walk as they head to court, and it’s clear just how unsympathetic and crude such mobsters really were—nothing like the strangely appealing Tony Soprano. As the reporters badger them for a statement, one of the crew’s top soldiers tells the newsmen: “Fugettaboutit. Go get a job.” That’s about the level of sophistication of the real mob.

Hollywood will no doubt continue to find new and innovative ways to package the Mafia, as Chase did brilliantly in his series. But for a sobering dose of reality, get your hands on a copy of Confessions of an Undercover Cop.

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More by Steven Malanga:
Borrowing Trouble
Why the State and Local Pension Problem Will Get Worse
Grassroots Soccer Mania
More . . .
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