Famous Fictional Mob Bosses

Don Corleone, The Godfather Tony Soprano, The Sopranos Frank Costello, The Departed Paul Cicero, Goodfellas

One a.m. that night: Conversation between Philly and Dan Pearson.
Dan: Hello
Philly: What are you doin’?
Dan: Sleeping.
Philly: Oh. Listen, is your friend a cop?
Dan: Who?
Philly: Your friend, the Pen.
Dan: Mike? Are you fucking kidding me? He’s a writer.
Philly: How sure are you?
Dan: C’mon, man. Do you really think I would bring a cop around you? I can’t believe you would even ask that.
Philly: You’re sure?
Dan: He may be Irish and a little out of shape, but he ain’t a cop. He’s a writer.
Philly: All right. You vouched for him. Don’t forget. [click]

*  *  *

Frank and Philly were officers, Operating largely above the Mafia’s daily grind. One of the aspects of the Mob I was interested in was the life of the soldiers, the guys who struggled to “make a nut” for their bosses, often with their fists. Had anything changed for them? To help me find out, Pearson arranged a ride-along with a couple of street guys we met in Brooklyn under the overhead tracks of the subway. Loud noise, Pearson explained, interferes with any potential microphones.

“I don’t have to pat you down, do I?” asks a soldier named “Jo Jo” (no relation to the “Jo Jo” arrested in the bust) when the meet goes down. Jo Jo stands 6'3" and weighs over 350 pounds. His head is shaved, and he wears a light leather jacket, blue jeans, and white sneakers. And one thing becomes very clear—if I piss him off enough, he will have no problem killing me, and it will not so much as affect his appetite.

“Don’t take it personally, pal,” he says. “Paranoia keeps you alive in this line of work. Even if it means the untimely demise of someone else.”

Teddy, another soldier, laughs. In this world premature death seems inevitable, but remains a steady source for humor. Teddy also has a nearly shaved head and a stocky build. His demeanor is calm and measured, like a man who feels like all his words are being recorded for posterity, thanks to the Feds. “No offense, buddy,” he says. “But that’s him talking. I ain’t saying shit today.”

With pleasantries exchanged, Pearson and I get into a white, sparkling clean Cadillac Escalade and head to an innocuous family-style Italian restaurant nearby for lunch. “In this life you don’t have an office,” Pearson explains. “You bounce around all day from one place to the next. Restaurants are one place where you get to spend a few hours off your feet talking. I think that’s why all Mob guys are huge. They eat all day.”

At lunch Jo Jo and Teddy explain how they got into the “family” business. “Most of my family was in the life,” Jo Jo says. “It’s no different than if your grandfather’s a cop, your father’s a cop, so you become a cop. They were gangsters. They used to send me into stores to start trouble. They’d say, ‘Here’s a hundred dollars. Go into this store and punch the guy behind the counter in the face.’ Then they’d go in and offer the guy protection for a couple hundred a month. So the store owner is paying
protection to the guy who’s causing him trouble in the first place.”

After a ridiculous amount of pastries and homemade grappa, the check arrives. The bill comes out to over $400, and it gets passed around to me. “You got this, right, pal?” Jo Jo asks. “Tell Maxim to pay for it. Listen, how do we get 20 percent of what Maxim earns?” That is the question every gangster asks himself: How do I get 20 percent of what you have, in perpetuity, until you’re dead?

“All right, pal,” Jo Jo says as we leave. “Let’s take a ride and do some business.” As we head for Manhattan, I imagine this is what it is like to be a hostage: sitting in the backseat with no mention of where you’re going, whom you’re seeing, or if danger might be forthcoming.  
               
“Don’t shit yourself,” Teddy says. “If it was going to be serious, we’d be carrying guns.”

Working for the Mob, Jo Jo explains, is like any other job, only a street guy doesn’t pay taxes to the government; he pays them to his family—in this case, the head of his crew. A good earner might kick as much as 50 percent of what he makes. The head of his crew takes a piece and kicks the rest up, and so on. For that tax, you receive the protection of the family. If you’ve got a problem, you’ve got the muscle to solve it.

The flipside of that equation is that there are no mitigating circumstances surrounding that 50 percent.

“When business gets bad,” Jo Jo adds, “you get laid off. We get killed. Some guys can’t take it and get out. Former street guys are everywhere—cops, firemen, Wall Street.”

After getting in the car, Jo Jo informs me of the next destination. They’re on their way to see someone who owes them a favor. The guy stopped returning calls, and the worst thing you can do to a Mob guy is try to ignore them.

While driving, Jo Jo daydreams about life after crime. “I won’t miss a bit about this—the ulcers you get when you need to make your nut. I’d like to get married and have kids like you have. But this isn’t a life for a father. I’ve put my sister and her kids through enough being in and out of jail. I’d like to kick back and relax. And with all the money being thrown around today, there has to be a better way.”

As we head into midtown, Teddy warns me, “Buddy, you better think twice before you go into this office with us. Whatever happens, happens. If it goes the wrong way and you’re standing there, you could get hit with a conspiracy charge.”

“See,” Jo Jo says. “You think we’ve been afraid of being identified, but we’ve been protecting you all along. If you knew who we were and what we were doing, the Feds would be knocking on your door.”

“So,” Teddy says, “you want to come over to the dark side?   
“No, thanks,” I say. Pearson and I get out of the car on Eighth Avenue.
“If you want to meet up with us later,” Jo Jo says, “I’ll give you a call around midnight. I’m sure your wife won’t have a problem with that. And bring that Maxim credit card, motherfucker.”

*  *  *

Three  weeks after the bust, prosecutors offered plea deals to 60 of the 62 defendants. “As a practical matter, it is highly unlikely that all 62 defendants will proceed to trial,” Assistant U.S. Attorney Joey Lipton wrote in court papers. “Plea agreements will likely reduce the numbers.” Only the two defendants charged with murder—Charles Carneglia and Nicholas Corozzo —were not offered a plea.

A few days later, I meet up with Philly again in Little Italy. The restructuring is going according to plan. “No one is making any big new moves, but all the business from before the bust is still happening. A lot of the guys are out on bail already. I told you this was going to go away.”

Despite the relative calm in the organization, Philly is more nervous than ever before. He looks disheveled and almost prefers to talk about Mob life than his personal life.

“My ex-wife served me to get additional child support,” he says. “I have a week to come up with the money. If not, I violate my parole.”

In fact, the government has already started to seize some of his assets, including his current wife’s car. “They even took my kid’s car seat,” he laments.

Because he’s close to going back to jail, Philly has decided to stay away from anything that has his name on it—cars, the house, the office. “They’ve got to be following me,” he says. “I wasn’t even parked in front of my house when they took my car. How did they know where it was?” Philly compares his plight to that of the other 61 guys who were busted.

“It’s all about money,” he says. “If you’ve got it, you can get a good lawyer and stay out of jail. If not, you  do time. It’s part of the job.”

Some things never change. Early death, vast segments of a life swallowed by prison, betrayal at the hands of your closest friends. Why still do it? I ask Philly.

“I would never want to do anything else. The money, the girls, the action—what more could you ask for?”