Underboss: Summary & Review

underboss book cover

“Underboss” (1999) is the life history of mobster Sammy Gravano up until he turned government witness against his former boss John Gotti and (a good chunk of) his associates in 1991.
“Underboss” is written by Peter Mass, but since it’s heavily based on Gravano’s own account, it feels like an autobiography.


About the Author: Peter Maas was an American journalist and author. He wrote several books about important figures in the criminal words. Much of the book is based upon Sammy “The Bull” Gravano, a gangster in the Gambino family who participated in the hit on former boss Paul Castellano and reached the Underboss position under the newly elected boss John Gotti.

The Beginnings: Learning the Use of Violence & Power

Gravano didn’t have an easy childhood.

At school, he used to often be in the middle of problems. Sometimes, self-created, and sometimes, because he’d always fight back any slight.
And he did receive quite sneering and bullying, partially because he was dyslexic and “easy to make fun of”.

But he always fought back, and sometimes, he learned that it paid.
He says:

If someone ridiculed him, he beat him up after school. That instantly ended the slights. “That’s when I found out that violence paid,” he says. “They stopped laughing.”

Power > Violence: It Hit Gravano Hard When He Realized

Two union goons walked into Gravano’s shop, and started threatening Sammy’s father.

Saviano thought to himself “there is no way I’m gonna get these two bums harm my father”. And he armed himself with a gun. But it wasn’t needed.
It wasn’t needed because Sammy’s dad knew the local mafia boss: Zuvito.
Sammy was flabbergasted.
He thought:

What good’s he?

He’s a frail little old guy, half the size of my dad. A strong wind would knock him right off his feet. I don’t know Cosa Nostra. I don’t know Zuvito’s power. I’m a kid. I’m with a gang. My thing is to fight with my fists.

And, lo and behold, the two goons go back and apologize a million times, plus pledge their help in case Sammy’s dad needed anything.
All because of Zuvito.
And that made Sammy all the more interested in understanding -and possibly acquiring- that type of power:

“That really opened my appetite to know more about Zuvito, what the hell he was, what made him so feared. Boy, I thought, wasn’t it something to be that physically unimposing and still have that kind of power and strength? I really didn’t understand it then.

Sammy was obviously a guy who enjoyed power.

Pick Your Battles: Avoid Being In Constant War

Gravano was impulsive, in some ways.

And he did sometimes act impulsively, almost always because of honor, revenge, and keeping his status and rep as a honorable, tough guy.

But he wasn’t impulsive all the times, and he was also smart.
Most of the times, he knew when to step back, and when to find alternative solutions to escalations.
For example:

He was robbing us blind, the cocksucker. “Now Ralph Spero ain’t a made guy. But it’s an awkward situation. He’s Shorty’s brother and I’m with Shorty. I decide it was better to sell the joint, get the fuck out. (…) I tried to avoid confrontations (…) there’s enough people to shoot in the head without looking for it all the time.

If People Don’t Respect Their Partner, They’re Not Going to Respect You

On keeping your partner’s honor:

“Once he told me that Carlo Gambino had spotted him in some restaurant with a girlfriend, whatever, and Carlo had called him over. In Italian, Carlo said, ‘Where’s your wife? What are you doing with this putana in a place like this where you’re seen by people who know you and your wife? Don’t you have any shame? Don’t you have any pride? Don’t you have any respect for your wife?’ “Toddo didn’t take offense. He thought Carlo was right and he was wrong. If you couldn’t be loyal to your wife and your children, how could you be loyal to Our Thing.

Why would you avoid that?

He wasn’t talking about somebody who just goes with a woman on the side. Every man, I think, does that at one point or another. But you don’t flaunt it. Put some shade on it. Like your wife could walk into a beauty parlor and other women are going to be there laughing behind her back. You put her in this position. You’re the one who belittled her. You want to sneak away somewhere, sneak away.

Read more here.

Machiavellian Strategy: Send a Double Agent

Old trick, but always valuable.

A double agent is someone who is on your side, but who pretends to be dissatisfied by you, and ready to turn on you, badmouth you, or generally happy to hear others complain about you.

Then, the double agent will report everything back to you.

Says Gravano:

“To keep tabs on him when I’m not around, I have Mike DeBatt play up to him. He tells Fiala that he wants to continue to work for him as a bouncer, how I always underpaid him. And now I know Fiala doesn’t have a clue who I actually am. He’s saying to Mike behind my back, ‘Fuck this Sammy. Fuck this punk. When I take over, I’m doing this, that.’

Fiala’s mistakes:

  1. Not checking who Gravano was
  2. Running his mouth

Social Strategy: Don’t Badmouth Your Frenemy (or he turns into an enemy)

Paul made a big mistake: he let word out that he didn’t like John Gotti.

Now from a “frenemy“, he pushes Gotti further and further into full enemy.

When Paul started talking, the word started spreading that he was going to demote John. And you know what demotion means in the mafia: it might as well be the prelude to getting whacked.
Says Gravano:

Paul is already talking about when Neil dies, he’s going to close down the Ravenite. He’s going to break John down to a soldier, stick him somewhere in a crew, maybe under Joe Butch, and treat him like a fucking hard-on. Without even being dead, he’s finished. “Then there is the possibility they would move on John and kill him.

What do you think that’s going to do for John and his crew?
John was below Paul, but he had his own crew as well, he had people around him who liked and supported him.

When those rumors spread, for John Gotti it started being a matter of “kill or get killed”. And that certainly pushed him hard to look for a way to attempt at Castellano’s life.

Machiavellian Tip: Don’t Go Overboard With Machiavellianism

… And never flaunt it!

Says Gravano, talking about John Gotti:

“’Listen to me,’ he says. ‘Keep them broke. Keep them hungry. Don’t make them too fat.’ “I can play Machiavellian like John—John was always quoting Machiavelli, I guess he did read him

I don’t know if this is true, to be honest. It might be, or it might not. Still, it’s not the type of advice you want to give to your underbosses, because that signals you’re not a true collaborator.
It signals that you want obedience and that you are ready to deploy highly value-taking, coercive, and abusive ways to reach your power goals.

And that decreases your social capital, your persuasive power, and increases the odds of a betrayal.

Take the Loss: It’s Good For Long-Term Business

Sammy was in construction, and one project was turning out to be a loser.

His business partner advised him to pull out and cut the losses.
Sammy replied:

‘You’re right, they can’t do nothing, but you know what will happen with that? Everybody in the world will hear about it. For everybody in the world we do work with, it’ll be Sammy does work and makes money, all well and good. If he loses money, he’ll abandon you. How do you think that’ll sit with people, Eddie? This will be the best two hundred thousand I’ll ever spend because people will say not only is Sammy qualified to do the job, but he’ll stay with you, win or lose.’ “’That’s important to businesspeople, Eddie,’ I said. ‘That’s why you were never successful in business. Because you scheme too fucking much.

“Because you scheme too F. much”: let that be your warning.

Leadership Tip: Don’t Isolate Yourself (or you get whacked)

Let me preface this:

In a way, Paul Castellano was a genius businessman.

The mafia has a great advantage in doing business: it can threaten, strong arm, intimidate and, if needed, resort to violence, exact revenge, or corrupt juries if it goes to court.
And Castellano was one of the best bosses in leveraging that “criminal edge” to expand the Gambino’s empire into legitimate and semi-legitimate businesses.

However, a skilled businessman doesn’t necessarily make for a great leader.
And especially not for a crime family.
That’s where gambino failed: as a mafia boss.

Let’s start with the first mistake: isolation.

Gravano says that Paul Castellano died, in good part, because he self-isolated from the family:

Castellano’s mansion on the hill perfectly symbolized a growing reclusiveness that over time would ultimately prove to be his undoing. By effectively abandoning his presence in the family’s social clubs, he began to lose touch with the pulse of the streets (…) He saw himself as a man with far-flung business interests. This led to a widening division

Leadership Tip: Be Like Your Team (or you get whacked)

Paul Gravano was unlike the gangsters in his crew.
Says Gravano:

He didn’t understand gangsters. He didn’t understand what the fuck it was to be broke, to have to go out and rob and do certain things. He didn’t understand what a gangster was all about, obviously. I mean, he didn’t really understand gangsters like John Gotti and Angie Ruggiero, or me or Frank DeCicco, anybody who is a real hoodlum or gangster in that sense of the word.

Still, in the beginning, Gravano thought highly of Castellano. He thought he was intelligent and wise, and knew how to move.
But Castellano made too many mistakes, and instead of being seen as smart and beyond being a gangster, he highlighted how he was the opposite.
For example:

“Afterwards, Toddo told me Paul had said to him, ‘What’s with this Sammy, going out on a hit in his condition? I thought he would just assign his people to the contract.’ ‘What can I tell you?’ Toddo said. ‘He’s got the balls of a fucking elephant.’ Toddo said Paul kept shaking his head, like he couldn’t get over it.

Paul doesn’t understand that for Sammy doing the hit himself was a question of honor.
Guys like Sammy want to hit back, as soon as possible. By “not understanding”, Castellano was also saying “I’m different than all these guys”. And people don’t want leaders who are too different from who they are.

Read more on leadership psychology:

And read here a primer on leadership.

Leadership Tip: Don’t Badmouth Your Team Members

Says Gravano:

“When I broke my ankle with that biker, the first thing out of Paul’s mouth was ‘Sammy, what were you doing in there? You’re a made guy. You don’t belong in those clubs anymore. This is beneath you.’ “I said, ‘Paul, it’s my club. I’m trying to put things together.

See what that idiot of Paul did there?
He indirectly told Gravano he was a failure for managing clubs. How’s Gravano supposed to feel when his boss says that? He’s going to dislike him, of course, because thas is offensive.

And he pushed down the people in his team both directly, and behind their back.
For example:

Even with Frankie DeCicco, when there was a business partnership we wanted to go in, Paul says, ‘Frankie? Frankie’s a gambler. He’s a street dog, Sammy.’ This was Paul’s mentality.

Those guys are going to be in business with Frankie, and now they’re going to feel like they’re in business with a street dog. Even if they don’t tell Frankie that, they still feel demeaned by their boss.
Plus, the boss loses status by behaving “un-leader like”. Leaders don’t crap on their own teams!

Leadership Tip: Earn the Respect of Your Team

Paul Castellano had an issue:

People didn’t really recognize him as a gangster.
And if your crew is made up of a large chunk of gangasters, that can become an issue.

He could have worked around it, or done something about it. Instead, he compounded that issue.
Says Sammy:

—all the guys in the family who regularly killed for Paul, the guys Paul sent out when he wanted somebody hit. “And Paul says, ‘You know who the true tough guys are? The cops. “You could have heard a pin drop (…) “As we walked out, Roy DeMeo, said, ‘Next time he’s got a hit, he should send in the fucking cops!’ “Paul was so out of it, saying a true tough guy is really a cop. That’s not a gangster talking. You don’t tell a gangster something like that.

So not only was Paul not earning the respect of his gangaster crew, he expanded on the thread of:

  • Not understanding gangsters
  • Not respecting gangsters
  • Being a poor gangster

If you are unlike your team, and if your team can’t look up to you, that’s already an issue.
But if the team starts to feel put down and embarrassed by what you say, then you are going to lose power as their boss.
And, eventually, your team might turn on you.

Ideally, great bosses are great at what their own team members do, or have been great at the past or -Castellano only had a couple of failed stick-ups-.
Failed that, at least, the leader should respect and recognizes the contribution of his team -Castellano seemed to scoff at the gangster way and preferred to be seen as an “industrial magnate”-. That created a major rift.

Leadership Tip: Don’t Steal From Your Team

Might sound like an obvious tip, but it’s not so obvious.

Once you have the power to steal, then stealing also becomes possible and might become more “normal”.

Paul Castellano received $40.000 from Gravano twice, by mistake. And he never gave back to Sammy what was rightfully his.
This is how Sammy put it:

“He said, ‘This guy gets his hands on money, he never gives it back. He’s never bringing up that forty again.’ “I said, ‘Are you nuts, Frankie? He’s got a trillion dollars (…) You mean to tell me he’s keeping my end?’ “Frankie said, ‘I tell you what. A steak dinner he never brings it up.’ We shook hands. It’s a bet. “Well, I bought Frankie the steak dinner. I couldn’t believe it. That bum kept the forty thousand.

Do you think that increased trust and loyalty in Sammy, or decreased it?
Obviously, it decreased trust.

Furthermore, Paul was skimming for himself, and lining up his pockets. That meant “taking away from the family”, and destroyed trust and any social capital Paul had with the family.

Leadership Tip: Defend Your Team

Yet another mistake from Paul Castellano was to not defend his team.

Says Gravano:

It was as if Castellano, beset by the unrest brewing in his own family, was seeking allies in other families. “We had this captain up in Connecticut,” (…) The Genovese people hated him because he was their competition. They come up with some concocted story about how he was a real pain in the ass. They want permission from Paul to hit him and he gives it and they do kill him. For being a thorn in their side and a pain in the ass? He was doing his job for our family. He was doing what he was supposed to do. And Paul gave him up, a captain in our family, in two seconds, against every Cosa Nostra rule.

How are other team members supposed to feel about that behavior? Like they are worthless pawns for his leader, and that they can be sold at the drop of a hat.
Instead, show that you’re on the side of your team, and ready to support them.

Indeed, Gravano says later:

“It was a big disgrace for the family. A real black eye. You give him up in five minutes to the Genovese family? Would you want your father giving you up like that? That was a bad, bad move Paul made. A real bad move. You want to know your boss is going to fight for you tooth and nail. But now you’re not so sure anymore. Probably, he thought it was a good move business-wise or racketeering-wise, but gangsters don’t think like that.

Leadership Tip: Keep Your Ego in Check

Leaders who do it for the team command more resources from that team.

Leaders who put “me” first tend to attract a few groupies, but they tend to lose social capital from more high-quality individuals who don’t fall for that “great man” myth.
Says Gravano:

“That’s why all the old foxes in Cosa Nostra hated him. And a lot of the bosses. It wasn’t the life. Just like when we said Paul Castellano was being selfish about money, this was equally selfish. Because it was for me, me, me. It wasn’t for Cosa Nostra. Cosa Nostra was supposed to be family. Not me, me, me.

Leadership Tip: Admit Your Mistakes

Mistakes and corrections are crucial aspects of power dynamics.

Some mistakes can decrease your status and authority.
Yet, never admitting mistakes also decreases social capital. Says Gravano:

“All John had to do was come to me once during that eleven months we were in there together and say, ‘Sammy, I’m sorry. My big fucking mouth got you indicted, number one. Number two, let’s try to get a severance for you, so you could fight your case. Fuck the public. Let’s try to fight this so that one of us, all of us, a couple of us, get out of this fucking mess. “If he done that, I would have never cooperated with the government, not in a million years would I have cooperated.

We don’t know if what Gravano says is true.
He might have cooperated anyway, who knows. But never admitting mistakes is dangerous for a leader, while taking ownership of mistakes can be a fantastic tool to increase trust and increase one’s own social power and persuasion.

Also see this forum thread:

Political Savvy Tip: Watch Out For Your Boss’ Tests

In the mafia, where scheming and plotting are embedded in the life, testing others can make the difference between life and death.

Here’s how Paul tested Gravano:

Paul threw down a newspaper in front of me. It was open to a page. ‘Here, read this,’ he said, walking all around. The story was about Roy DeMeo being found in the trunk of a car. “’What do you think of that?’ he said. He don’t know that I know that he gave the order. He’s being devious. He wants to see my feelings. Like maybe I would say, ‘Hey, Roy was my best friend. I’m going to get even with whoever the fuck did this.’ He’s trying to gauge my reaction.

How did Gravano react?
He took the opportunity, of course.

First off, he didn’t react too quickly, or that would have seeemed fake.
Instead, he read the newspaper first, and then:

“So what I did as soon as I got done reading the article, I looked at him and said, ‘Paul, if you’re mad, I’m mad. If you ain’t mad,’ I said, putting the paper aside, ‘I don’t give a fuck.’ “He looked at me and said, ‘Oh, all right. You want something else with the coffee?’ Those were his exact words and it was over and done with. I guess he was happy

Read more on:

Life Strategy: Make Friends, Not Enemies (& Don’t One-Up)

This is John Gotti, one-upping the people around and beneath him, making them feel bad, inferior… And resentful:

Although, on the surface, Willie Boy played the obedient Tonto to Gotti’s Lone Ranger, he seemed to take special pleasure in reporting what Gotti was up to. Gotti’s idea of humor left plenty to be desired. And Johnson seethed with resentment as Gotti delivered derisive asides about “redskins” and “half-breeds” and often treated him as a second-class citizen.

This guy testified only against Gotti.

Divide & Conquer Social Strategy

An interesting power move by Paul Castellano:

At this meeting, Paul mouths off that he should have had Sammy killed over the Fiala situation. This was classic Paul—divide and conquer. Paul saw and seized an opportunity to drive a wedge between us. The Fiala business was history. But Louie figured that it wasn’t resolved in Paul’s mind and panicked. He thought if Sammy’s going to be killed, he’ll be killed as well. He took Paul’s word at face value. He don’t know Paul well enough to know that Paul was just talking.

Basically, Paul made Louie think he might have ordered a hit on Sammy. And he thought that if he was too close to Sammy, he was in danger as well.
He saw a risk in being too close to Sammy, and he saw an opportunity in distancing himself.

Don’t Believe The Hype

One of the reasons Gotti fell, and one of the reasons why he ultimately weakened his family and mafia in general, is that he fell victim to his own hype.

Says Gravano:

I’ve seen a lot of smart people do stupid things because of an ego. John was no different. After a while you get power-struck. He started believing these newspaper and magazine articles, what they were saying about him on television. He went past having a big ego. You’re talking now about an egomaniac. He don’t want to hear the truth. He’s not looking for it. He’s looking for people to say what he wants to hear. Not only was the media having a love affair with him, he was having it with himself.

As a matter of fact, the more you become successful, the more you must be careful about ego and hype.
Also see this video:


  • Structure and collaboration = power

In 1931, warring factions of the Italian underworld, primarily Sicilian and Neapolitan, came together to form Cosa Nostra. This union enabled it to completely dominate organized crime.

Also read: strategies of power.

  • Be smart, and street-smart

Says Gravano:

You can’t be a thug forever if you want to get ahead. Somewhere along the line, you have to learn to be a racketeer as well. You can be both.

  • Your family doesn’t determine your path

Gravano had loving parents. And his father valued and rewarded honest working. He told Sammy several times. But Sammy seemed to have been “born” to be a gangster.

  • Teachers can help save children

Gravano, an undiagnosed dyslexic, had been kicked out from school, branded as a “lost case” by most teachers, and was ready to give up on school.
But one teacher almost saved him, restored his faith in himself and helped him catch up.
Says Gravano:

Because here’s a guy who’s put such an effort, an honest effort, into you, and you wanted to make him look good

But then he moved yet again, and it was back to the same usual thing of teachers giving up on him.

  • Always listen to both sides

Gravano’s mentor took him under his wings.
And right after he received one local man seeking help:

I’ll get back to you in a day or two.’ “After the guy leaves, Toddo looks at me and says, ‘Assume you were me, what would you do?’ “I said, ‘I’d get a couple of guys with some bats and send them over and break this other guy’s legs. I’d break everything he’s got.’ “’Good,’ Toddo says. ‘You got balls. And you’re young and you’re stupid.’
‘You know those things attached to the sides of your head? Those ears? Use them. Remember that in life. Listen with both ears. You listen to one story. You listen to the other one.

  • Justice inner works have a lot to do with power dynamics

“Underboss” shows that who the prosecutors go after, and what they’re ready to do for it, has a lot to do with “what’s in it for me”:

“This D.A., this bum Eugene Gold, who would get caught molesting some kid, don’t give a fuck about anybody except Mimi. He sees big headlines with Mimi. And this assistant D.A. comes to me and he says if I flip, if I testify against Mimi, I get a total walk. I’m out of the whole thing.

This isn’t just Gravano talking, by the way.
The simple fact that Gravano, who committed 19 murders got away with 5 years and a cushy witness protection program says a lot about how justice works.

  • If you’re in criminal organizations, keep your mouth shout

Like Toddo Aurello once said, ‘You do a hit, it’s over and done with. You talk about it and you’re doing it again. And it could wind up on tape.’”

And it worked for Sammy:

when the state’s organized crime task force eventually did decide to bug the office, thousands of hours of recorded conversations produced nothing of evidentiary value.

  • Machiavellian move: do good deeds if your name will be linked to it

Says Sammy:

“Then John made another play. He said that Cosa Nostra had to replenish our ranks. He brought up the fact that the Genovese family had forty replacements to make and hadn’t made any new members for a very, very long time. John figured if he could get Chin to agree to make these forty guys, he would leak it that he was behind them being made and they would ultimately look to John.

Chin being a smart guy, he said that “he appreciated John’s thought, and that he would make new made men when he thought it was appropriate”.

  • To have a top organization, you need top people

One of the reasons the mafia was so successful in the underworld is that they enforced and maintained certain rules of conduct and certain expectations from their people.
Compare it to the Irish gangs, for example. Says Gravano:

“They were just supposed to give this O’Connor a serious beating,” Sammy said. “But a lot of the Westies were all fucked-up, drug addicts and drunks. And they end up shooting O’Connor in his legs and ass for whatever reason. So now when the D.A. eventually gets into this, it’s a major thing.”


On himself using racial slurs but not being racist:

Now I use words all the time like nigger, spick, Polack, jewboy, Mick, even greaseball, which is people from Italy. That’s just the way you talk on the street. I don’t think I’m racist. But these rednecks, they are real hard core.

On the gender split of the hairdresser’s school he (half-)attended to get government money:

There’s about six hundred girls in there, full-time and part-time. And only five guys, including me. Two of them are stone faggots. You can consider them women.

How a street cred helps collect money:

When you’re dealing at that level, you’re lending to the bottom of the barrel (…) But even so, during those years, there’s only two people I had to hit to collect. Physically hit, I mean. Only two people. I think that says something about the reputation I had.

On the intricacies, Machiavellianism, friendship, and betrayal all embedded in the mafia, at once:

That was some irony there. Here was Joe Colucci joking and drinking it up with Tommy, who was coming on to his wife, the guy Joe wanted dead. Here was Frankie, who was in on both sides of the story. And here was me, on my first hit, the hunter and the hunted, all at once. Just another day in the life of organized crime.

On the mentality of Gravano, notice what he says at the end:

Joe Colucci was dead. He looked like he was sleeping. He looked peaceful. You going to blow me away now? I thought.

On how he felt after his first hit:

But then I felt a surge of power. I realized that I had taken a human life, that I had the power over life and death. I was a predator. I was an animal. I was Cosa Nostra.

Marry the good girl.
It’s especially a good idea to keep you balanced.
Talking about her future wife she saw in a club:

But I’m watching Debbie. She looks so out of her element in that place. I mean, I’m used to seeing a certain kind of woman in there and she is not that kind of woman. She seems so fresh, so innocent. More than anything, that’s what caught my attention.


I saw her in the kitchen. She had an apron on, she looked like a little housemother, cooking away, cooking and tasting the sauce and the sausage and the macaroni. She was so different from the sluts that I’m dealing with every other minute at the club.

On the friction between “honor” and “criminality”:

Toddo was an honest man within the life. It may be hard to understand that. He was a gangster and a crook, but to us he had honor.

And a good video:

Her: Don’t you see the irony of Sammy the Bull pleased that people have good manners?

Him: That’s because you’re not a mobster and never was

What a genius retort.

Again, on honor:

Gotti was a big-time player and a big-time loser. He always paid his debts, not out of some moral sense but because to do otherwise would bring about immediate dishonor in mob circles.

On Gravano being the happiest when he became a made man (and this was a man who was already a father by then):

They’re calling one guy at a time to go to the basement. I’m as high as a kite. I mean, this is the biggest day of my life, especially at that point. Finally, I’m told, ‘Sammy, we want you to come down.’ “I’m nervous as hell, but happy nervous.

Again on mafia, even including the betrayal, still also being about honor and brotherhood in the mind of (some) of its members (even while Gravano himself says that he realized late it was BS, it was no less real):

“I bought this all one hundred thousand percent. I really felt that I belonged to a brotherhood that had honor and respect. All the things I looked for in life was in a good part of that oath.

On the unfair advantage of using threats and fear doing business:

When the immensely wealthy owner of the Waldbaum chain that bore his name was asked by a presidential commission on organized crime how he could have knuckled under to the Mafia, he replied, “Don’t forget I have a wife and children.”

On honor and “dying with honor”:

Like the man he was, the man I had come to understand him to be, the man I’d learned to respect over the past hours, he accepted this without comment. I felt terrible that a man with such balls had to be hit. But this was Cosa Nostra. (…) He died with dignity. He died Cosa Nostra.

A funny quote:

Unhappy with what he considered to be sloppy management, Sammy decided to take over the whole operation and got rid of the four original owners. “I just bullied my way in. I said I was going to make them an offer they couldn’t refuse. I didn’t have to explain. I imagine they all saw The Godfather.

When a hit needs to be done, to make sure it’s done, it’s the killed life, or the killer’s life:

These two guys have got to go. ‘Don’t worry about the cops,’ he says, ‘because if you run and these guys ain’t dead, we’ll kill you.’”

On negotiation and the advantages of “paying in installments”:

The head of the Westies had come to Sammy and told him that he knew someone on the jury who was available for a price. “How much of a price?” Sammy asked. The answer was $120,000. Ever the negotiator, Sammy whittled it down to $60,000, payable in installments. You never knew, he figured. The guy could get sick or something.

On Gotti wanting to be “known” (funny):

Piecyk found two cops and said that he had just been beaten and robbed. He led them back to the bar and pointed out Gotti and Colletta as his assailants. As Gotti was being handcuffed by one of the cops, he demanded, “Don’t you know who I am?” To his evident displeasure, the cop replied, “No, and I don’t care.”

(but that Piecyk later recanted and withdrew his complaint once he realized who it was).


  • True page turner: the most exciting, enthralling book I’ve read in a long time
  • Deep lessons: if you can read between the lines -important “IF”!-, it contains some of the best lessons learned on strategies, leadership, and Machiavellianism


For as much as I loved this book, there also important cons:

  • Self-serving in justifying his own “snitching”

Sammy turned informant, which is a big no-no in that life for anyone, and especially for someone at his level.

He justifies his choice by blaming it on Gotti and “the life” that was all fake, he says.

But this is what Michael Franzese, a former mobster who did not put anyone in prison, said about Sammy “turning”:

Sammy also laid it on thick on John Gotti.

Gotti wasn’t perfect, for sure, and as far as I know, Gravano might be partially right. Yet, some of the accusations he moves to Gotti feel so exaggerated that you’d just think they’re fake.

Even some of the reasons he provides for disliking Gotti feel conveniently self-serving.
He says he started disliking Gotti because he cheered for Iraq in the Iraqui war, while Gravano instead didn’t want “our kids”, the American soldiers, to die.
Then Gravano was given a military jacket when it was raining outside and he happened to “remember” his days in the army, and now he felt so “American and patriotic”.

What a convenient narrative though, eh?

  • Some parts of the story don’t add up

Some elements don’t add up.

When Gravano told his wife and daughter he was going to collaborate, his daughter turned hysterical.
And his own wife decided and told him right there and then that she wouldn’t go with him under witness protection.

Why not?

Gravano paints a picture of a loving wife.
But that’s not how a loving wife behaves. She wouldn’t leave the moment she gets to know that he was going to join the family again sooner rather than later.

  • Paul Maas own opinions feel like empty and shallow moralizing

Says the author:

The fictional Godfather was myth-making at its most compelling (…) Never mind that loyalty and honor played no part in the actual Cosa Nostra. Perceived reality was what mattered.

That’s the author’s own opinion.
But it’s not true, and his own book disproves it. Even for Gravano, who later testified, honor was a big part of that life -just read the quote-.

Many of those guys’ goals was to “be a man’s man”, to be honorable and respected.

Yes, you might say “honor” was, at least to some extent, a manipulative tool to increase cooperation from others while leaving down the door open for individual’s defection.
But it was still part of that life, and of its allure.


“Underboss” is the book I devoured the quickest in the last year.

It’s because I usually read “heavier” books, while this is more the type of book that you read for personal pleasure.
Yet, there are more lessons learned in “Underboss” than in most self-development books.

Especially, “Underboss” is a treasure trove for power dynamics, social strategies, and Machiavellianism.

Also read:

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