7 Habits of Successful Mob Bosses

Alan Schnur
5 min readMar 2, 2020


Benjamin ‘Bugsy’ Siegel

Bookstores and the Internet are filled with thoughtful and illuminating studies of great leaders. Men and women who have overcome immense challenges as they led their troops into battle, CEOs who produced outstanding results in the corporate arena, coaches who created championship teams, and, among others, visionaries who saw possibilities and achieved goals few, if any, thought possible. Indeed, literature is littered with stories of intrepid women and men who have, through their abilities to mobilize, motivate and inspire teams of people, led organizations to greatness. Such is the power and legacy of their leadership skills and their determination to win.

Yet, one important reservoir of exceptional leadership talent has been largely overlooked by these studies. A group, typically male, who have amassed great success by creating enterprises filled with highly loyal, motivated, and entrepreneurial individuals who support the leader’s vision of sustaining healthy business growth by: identifying new revenue sources; hands-on, personalized, face-to-face customer service; strong persuasion skills; timely billing and collection of fees for services rendered; and, effective execution of the organization’s hallmark tactics. A group of hand-picked and carefully-trained employees who, together, form the organization’s competitive advantage. All because of its chief executive.

To their credit, this select group of leaders tends to be:

  • Outstanding judges of talent and character
  • Attractors, developers and retainers of top talent
  • Highly capable mentors
  • Strong administrators of the organization’s HR policies (which are unwritten but clearly known and understood by all)
  • Effective communicators, and
  • Unflinching when confronted with poor performance, whether it be employees or customers.

These men lead by example, are values- and results-driven, reward loyalty and performance handsomely, and promote exclusively from within. They have outstanding ‘executive presence,’ commanding attention wherever they go. Given their heralded accomplishments, they are an ideal group to study. Save for one, small, somewhat unsavory drawback: they head criminal organizations.

I speak, of course, of mob bosses.

Some context may be helpful. Mob bosses oversee and run large, diversified, for-profit organizations. The boss typically has absolute or near-absolute power over the members of the enterprise, is greatly respected and feared for his or her ruthlessness and willingness to exert physical and psychological influence over those who are uncooperative or those who underperform, and the one who profits most handsomely from the criminal endeavors in which the organization is engaged.¹

Despite their involvement in crime, which may, for some, be a bit of a turn-off, there are seven valuable lessons to be learned from this industrious group. To be fair, I must not be alone in considering mob bosses as a font of useful information. Our current president appears to have studied and assumed many, if not all, of their core characteristics and the lessons learned from each. Which include:

1. Creating an all-cash, recession-proof enterprise that generates significant revenue and healthy, sustainable profit margins. Mob bosses explain that it’s best to inherit such a business from an older relative, like a parent or grandparent, as it saves time and hassle. Mail-order steaks, commercial airlines, and online universities are reasonable ventures for the less ambitious. Casinos are typical go-to businesses, since they are cash cows and are near-foolproof. Golf resorts have their appeal, too, as they offer viable money laundering opportunities. Construction is ideal. Diversification is wise. Foreign investors should be considered with caution, as they offer new, possibly highly-lucrative markets but also introduce significant risk. Beware of any quid pro quo, as Russians, for example, will expect ‘favors’ (like election tampering) to be well-compensated. The attached ‘strings’ may be onerous.

2. Building an organization with trusted people who will become beholden to you. Don’t count on money alone to be the bond that binds. Fear is effective when assuming and maintaining control. Ruthlessness is better. Name calling works, too, but only for the novice. And remember: even the best people are expendable. Be prepared to rotate in new loyal staff as old ones are defamed in public and/or ‘retired.’

3. Crushing the opposition while continually threatening allies. It’s all about power. Use every tool available to manipulate and control those who might oppose you and those who are currently your allies. Because allies can become enemies in a flash. Be ready for that eventuality.

4. The willingness — the audacity — to break laws in broad daylight. Many will tell you that the cover of darkness is for the weak. If you have real power, you can shoot someone on 5th Avenue and get away with it. Since it’s about having real power — power that others can see — consider a dramatic breaking of the law in daylight from time to time, even in front of television cameras. This is how respect is earned — and maintained.

5. Shaping ‘the truth’ to whatever you say it is. You’re the Boss. If you say it’s legal, it’s legal. No vig is too high.² You define what’s right and wrong. The more often you say it, the louder you say it, the quicker it becomes fact. If you’re good, the media will support and validate your ‘truths,’ further defining your power, and, critically, expanding the number of people who respect you. Even if there’s no truth to it.

6. Creating a justice system that works for you. The legal system, especially the courts, are yours to control. Judges and juries are there to be influenced. Create your legal playing field well before you need it. A solid foundation will enable you to protect, pardon or fully exonerate your friends — which is another way to engender loyalty, respect and control. And, sooner or later, you may need it, too.

7. Valuing family above (almost) all else. This is a family business. Your family is the source of your emotional strength, your raison d’être. Sons and daughters have a vital place in the business and in your heart. A wife is essential, too, though girlfriends (and/or boyfriends) play a critical role. (The latter is another reason to keep a significant amount of untraceable cash on hand.) Your loyal employees are family, too. Until they are no longer loyal, at which point they are no longer employees. Or family.

Mastering these skills may not be wise or even advisable, given their source and intent. Unless, of course, you seek or hold a high elected office, wish to remain there for years, and care not about the laws of the land or the future of the country. Washington, D.C. seems packed with students of mob bosses. Very good students, all things considered.

¹ https://en.wikipedia.org/wiki/Crime_boss

² A ‘vig,’ short for vigorish, is an excessive rate of interest for a loan, typically set by a moneylender. It often needs to be paid daily or weekly, depending on the terms defined by the moneylender.



Alan Schnur

Alan is a consulting psychologist with a long and storied history of helping organizations of all sizes become more enriching, empowering places to work.