Underboss Summary – October 2022

Author: Peter Maas

Short Summary
Underboss (1997) covers a lot of ground, from Sammy Gravano’s childhood in Brooklyn to his days as a made man in the Gambino crime family. Along the way, we get an inside look at some of the most notorious mobsters of the 20th century and the crimes they committed. We also see how power and greed can corrupt even the most loyal soldiers, leading them to betray their friends and family. 
Source: amazon.com

Detailed Summary

The Underboss book starts with Gravano’s childhood and adolescence in Brooklyn, where he first started getting involved in crime. From there, it goes into his years as a made man and underboss in the Gambino crime family, which included participating in several murders. It then details how he eventually became a government witness and took down John Gotti. “Underboss” is an interesting read because it gives insight into the mind of a mafia member. It’s also fascinating to see how Gravano went from being a ruthless killer to becoming a government informant. 

“Underboss” gives you a sense of what it’s like to be a mobster and how the mafia operates on a day-to-day basis. One thing that struck me while reading “Underboss” was how Sammy Gravano seemed to rationalize everything he did, no matter how heinous. He talks about killing people like it’s no big deal and in some cases, even tries to justify it. For example, he talks about how one victim deserved to be killed because he was cheating on his wife. It’s chilling to read, but it gives you a good understanding of the mindset of a Mafia hitman.

Underboss Key points

Badmouthing your frenemy is a surefire way to turn him into an enemy

In business and life, it’s important to be strategic about your relationships. You want to be careful about the company you keep and the way you interact with others, especially when it comes to those who may be considered your “frenemies.” A frenemy is someone who is both a friend and an enemy. They may be someone you compete with professionally or personally, but there is still some level of respect or fondness between you. It’s important to navigate these relationships carefully, as they can easily turn into full-blown enemies if you’re not careful.

One way to make sure you don’t inadvertently turn a frenemy into an enemy is by refraining from badmouthing them behind their back. Gossiping about them or speaking ill of them will only make things worse and could potentially damage your relationship beyond repair. It’s also important to avoid being drawn into their drama. If they are constantly starting drama or creating conflict, resist the urge to get involved. This will only make things worse and could put you in the middle of a feud that you don’t want anything to do with. 

So what should you do instead? The best course of action is to simply ignore them. If they see that you’re not bothered by their presence, they’ll eventually get bored and move on. Of course, this isn’t always easy. But it’s important to remember that the next time you feel the urge to badmouth your frenemy, doing so will only make things worse.

If you come across as too Machiavellian, people will see through you and your schemes

You may have heard of the “Machiavellianism” personality type – someone who is cold, calculating, and manipulative. This person is often successful in achieving their goals, but they are not always liked or respected by others. If you want to be successful in your own life without being a complete jerk, it’s important to use Machiavellianism sparingly. The problem is that if you take things too far, people will start to catch on and they’ll turn against you. So while it’s important to be ruthless and manipulative, you also need to know when to stop. If you push your luck too far, you’ll ultimately end up alone and powerless.

There are times when it’s helpful to be manipulative and calculate your moves carefully, but if you do it all the time people will catch on and they will start to resent you. It’s important to find a balance between being assertive and being liked. If you’re too Machiavellian, people will see through you. Be calculating and strategic, but don’t be so obvious about it. If you go overboard, people will catch on and they won’t trust you. Be sure to always act in your own best interest, and be willing to use whatever means necessary to achieve your goals. Remember, the end always justifies the means – so long as you don’t get caught.

No business wants to take a loss, but sometimes it’s the best thing to do for long-term success

We’ve all been there. We’re so close to closing a deal, but the other party just won’t budge on their offer. So we do what any good negotiator would do: we compromise. We give in on some points and they give in on others until finally, we have a deal that both sides can live with. But sometimes, the best course of action is to simply walk away from the table. It may seem counterintuitive, but sometimes the best way to win in negotiation is to lose – at least in the short term. By walking away from a bad deal, you signal to the other side that you are not desperate and that you are willing to walk away from a deal that does not meet your needs.

This can often lead them to come back with a better offer that is more favorable to you. Of course, this strategy only works if you are truly prepared to walk away from the deal. If you bluff and they call your bluff, then you will be worse off than if you had just accepted their original offer. But if you are confident in your ability to find another buyer or supplier who will give you a better deal, then walking away can be effective.

Underboss Quotes

“Remember that in life. Listen with both ears. You listen to one story. You listen to the other one. Someplace in the middle is the truth. It’s up to your brain and knowledge to determine what to do if you know the background of the people who are involved. Don’t ever react to anything in life—legitimate or illegitimate—by listening just to one side. You got plenty of time to react. Listen to both sides. Think about someplace in the middle and make up your mind. Then react. Then you do what you want.” –Peter Maas

“Sometimes, no matter how smart you are, you can’t avoid getting tripped up.” -Peter Maas

Crucial Conversation Review

“Underboss” is an excellent book for those who want to learn about the dark side of power. The book is full of strategies and tips on how to manipulate people and get what you want. While some of the tactics may be unethical, they are still useful to know. Overall, Underboss book is a fascinating read that provides valuable insights into the world of power and manipulation.

To whom I would recommend the Underboss Summary?

  • Anyone who wants to understand how successful people think and operate in relationships of authority.
  • Anyone who wants to know about human nature and the psychology of power.
  • Anyone who wants insights into criminal organizations.
Underboss Summary - October 2022

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