Tag Archives: Cosa Nostra

Management Lessons from a Gangster

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Management Lessons from a Gangster

Confession and trigger warning: I’ve been listening to podcasts of Sammy ‘The Bull’ Gravano. 

And I was surprised at some of the valuable management skills he used in his past day job.

Sammy ‘The Bull’ Gravano with John Gotti

If you’re not familiar, Salvatore Gravano was a big-time gangster and all-around bad guy, mostly in the 1970s and 1980s and mostly with the notorious NY Gambino mob, as a street guy, then a Made guy (formally initiated), then a Caporegime (or Capo, a captain with his own crew), then Consiglieri (think Robert Duvall’s Tom Hagen in The Godfather), and ultimately Underboss, reporting to the uber-notorious John Gotti – effectively, he was sort of the COO of the Gambino family.

Gravano’s boss, John Gotti

If Gravano had a LinkedIn profile, it would be pretty impressive – – loyalty to his organization, steady rise to top management, etc. – – falling short, however, in the areas of education (8th grade), and the fact that he, uh, spent over 22 years in prison. (I did check and no, he has no LI profile- yet).

Sammy ‘The Bull’ Gravano – mug shot 1990

His list of crimes ranges from the petty (stealing spare tires from car trunks when he was in a street gang) to shakedowns of various flavors, to the truly horrible – murder, either directly or as a planner, 19 by the FBI’s count (most famously, planning and executing the murder of the head of his own Family, ‘Boss of Bosses’ Paul Castellano, Gotti’s predecessor – in the middle of Christmas shopping crowds in NY in December 1985). 

DECEMBER 17, 1 The body of Thomas Bilotti lies by his car on E. 46th St. after Bilotti and Paul (Big Paul) Castellano, 70, were shot to death by three men, who fled. At the time of his death, Big Paul was reputedly the boss of the nation’s biggest crime family., (Photo by NY Daily News Archive via Getty Images)

The first lesson is compartmentalization.  I’ve always felt that there’s something to be learned from virtually everyone – from career mentors to role models to competitors to my dog Rizzo, who is super capable of being in the moment. It requires focusing on something important and ignoring everything else.

In this case, learning from a mobster requires the ability to separate the guy described above from the gruff, but relaxed and confident 77-year old you hear in the podcasts.  While he committed a lot of heinous crimes that can never be forgiven, at the same time he also has some interesting takes on his past that can be helpful to us ‘legitimate’ people.

  • Gravano is a master compartmentalizer – – rationalizing the crimes of the past and softening them with statements about how he always did the right thing or what was required of him after pledging loyalty.
  • Moral Hazard Disclaimer: You need to be comfortable with the fact that listening to his podcasts in some way puts money in his, and Patreon’s, pockets.

Lesson:  Loyalty to the organization, but with limits.  Everyone knows that the Cosa Nostra demands utter loyalty – above family and faith.  You do what the Boss demands without question, you keep him informed, you expect the same from those you lead.  The penalty for screwing this up was usually not living long afterward.

  • Gravano took his loyalty oath seriously but not blindly.  When the mercurial Gotti would order a hit, Gravano on multiple occasions would challenge Gotti’s command, encourage him to calm down and reconsider, rather than act on impulse and create bigger issues.
  • At the same time, after both of their arrests in 1990, when Gravano heard that Gotti had asked for a plea whereby he would throw Gravano under the bus, he reconsidered his view of loyalty and cooperated with the FBI against Gotti.
Testifying against Gotti
Friday, April 3, 1992 edition of the New York Post

Lesson: Win-win.  Gravano had outsized influence with labor unions on huge construction projects (not a few of which were Trump projects).  Rather than exerting influence through threats of violence, he created unique schemes whereby all parties came out ahead (except, of course, the people paying for the buildings) – ensuring the loyalty of those he got payments from. And while his education stopped at 8th grade, he had practical experience running construction companies and was adept at running the numbers.

See also:  Speak softly and carry a big stick

Lesson:  Loyalty to people.  Without question, personal loyalties were extremely important to Gravano, and he would go to significant lengths to help those he had loyalty to, even at personal risk, often for no financial benefit.

Lesson:  Planning.  Hearing the planning involved in some of the hits is eye-opening; sometimes it would take months. Staking out, detecting patterns, having plans and back-up plans, deploying decoy cars to block or distract police, etc.  The goal was to anticipate every possible scenario and cover for it.

Lesson:  Sunk cost.  Despite planning, sometimes the unexpected did happen – -and despite having lots of assets in place, at times Gravano would assess the situation and cancel the hit.  Considering the severe potential consequences of not executing the plan, this was no small decision.

Lesson: When in hole, stop digging.  Gravano was arrested in 1990 and served 5 years as part of a plea deal, released in 1995, moved to Arizona.  The end of roughly 20 years in the mob, with access to the Witness Protection Program (which he quickly opted out of).  Free to start anew.

Which he did. In 2002, he was arrested for running a drug ring, got a 20-year sentence and was released a bit early in 2017.  Oops.

He is by all appearances walking a straight path now.

Sammy ‘The Bull’ Gravano – podcaster

Final lesson: Adapt and survive.  This poorly-educated, street-smart, morally challenged 77-year old was previously mostly comfortable with a gun.  He is now a podcaster and YouTuber, and you can hear him grimace when he asks you to ‘Like and Subscribe’ at the end of his podcasts, as his handlers insist.  He also now does live ads for companies like watch company MVMT (“I don’t often take off my Rolex, but when I do, I wear MVMT” or “I know about doing time”), or counseling company betterhelp, or online insurance broker Policygenius. He also has a website and a number of other ventures.

Re: adaptability, see also: Madonna

It’s a strange world.  Competence comes in all shapes and sizes – – some of the most brilliant minds unfortunately are those of criminals, for example:

  • Hijacker D.B. Cooper
  • Hackers
  • Ted Kaczynski (Unabomber) – evaded capture for 20 years
  • Frank ‘Catch Me If You Can’ Abagnale (although apparently some of his stories are made-up, making them a different type of scam)
  • All the real smart ones who haven’t been caught

We can’t (and shouldn’t) benefit from the crimes of others, and criminals should not be rewarded for their crimes.

But there can be a benefit from observing criminal minds.