10 Management Lessons From Highly Successful Gangsters

By Jeppe Kleijngeld

Running a large company or criminal empire, what’s the difference? The demands for its managers and leaders are very similar for sure. As a leader, your vision needs to inspire others and your actions need to have significant impact. You also need to be able to effectively solve problems and prevent painful blunders. Taking a close look at 10 highly successful gangsters from popular movies and television series can be inspirational. Eventually most of them went down, but they all had impressive careers as criminal CEO’s. What can business leaders learn from their successful approaches and significant failures?

1. Plan all your actions carefully
Neil McCauley
The Gangster: Neil McCauley, Heat

The Lesson: In the spectacular opening scene of Michael Mann’s Heat, criminal chief Neil McCauley and his team of robbers manage to take down a huge score. The key to their success? Planning, planning, planning. McCauley is a perfectionist; every detail needs to be scrupulously prepared, nothing can be left to coincidence. It there is even a slight chance that something is wrong; he will walk away from a job no matter how much money is at stake. Off course, there is a slight bump in the road for McCauley and his team later on, but that is only because pulling armed robberies is a highly volatile business. But even with a terrific investigation team on their tail lead by a fanatical Al Pacino, they manage to take down another – even larger – score later on in the movie.

2. Build a team you can rely on
Joe Cabot
The Gangster: Joe Cabot, Reservoir Dogs

The Lesson: ‘I should have my head examined for going with someone I wasn’t a 100 percent on…’ Yeah, you should have Joe. As a manager, your most important task is to choose the right people around you and make them perform optimally. When you have a crucial project to realise – a diamond heist in Joe Cabot’s case – you don’t want to take any chances on whom you hire for the job. Joe’s negligence at this point, allowed a special LAPD-agent to infiltrate his crew, leading to a disastrous outcome for the project and all those involved.

3. Always look out for opportunities and know when to strike
Henry Hill
The Gangster: Henry Hill, GoodFellas

The Lesson: In Wiseguy, the novel on which the classic mob movie GoodFellas is based, protagonist Henry Hill describes his bewonderment at how lazy many people are. Great entrepreneurs like him are always looking for new ways to make money. Once in a while, a golden opportunity arises and a highly successful business manager will recognize this once in a lifetime chance and grab it. In Henry Hill’s case, this was the Air France heist in 1967. He walked away with 420.000 US dollars from the Air France cargo terminal at JFK International Airport without using a gun; the largest cash robbery that had taken place at the time. This was Hill’s ticket to long term success within the Mafia.

4. Analyse, decide and execute with conviction
Michael Corleone
The Gangster: Michael Corleone, The Godfather

The Lesson: Your success as executive depends for a great deal on the way you make decisions and follow them through. When his father, family patriarch Don Vito Corleone, is shot by Virgil ‘The Turk’ Sollozzo, Michael Corleone knows the threat of his father’s killing will not be over until Sollozo is dead. That is his analysis. Then, without any hesitation, he decides to kill Sollozo despite the hard consequences that he knows will follow. The third part – the execution – he performs flawlessly, killing Sollozo and his bodyguard Police Captain McCluskey in a restaurant. Michael later in the film again proves to be an extremely decisive leader when he has the heads of the five families killed when they conspire against the Corleone family.

5. Support the local community
Young Vito Corleone
The Gangster: Young Vito Corleone, The Godfather Part II

The Lesson: For long term success, you need more than just great products (in the mob’s case: protection, gambling and theft). You will need commitment from all your stakeholders and especially goodwill from the communities you operate in. Young Vito Corleone sees that gangster boss Fanucci is squeezing out everybody in the neighbourhood he lives in. Nobody is happy with him. So he murders Fanucci and takes over as neighbourhood chieftain. Rather than squeezing out people, he starts helping them. Every favour he does for somebody, earns him a favour in return. Those are a lot of favours and a lot of people who think he deserves his success and wealth. They are willing to give everything for their Don.

6. Don’t be afraid to use your subconscious
Tony Soprano
The Gangster: Tony Soprano, The Sopranos

The Lesson: As a leader, you want to base your decisions on hard facts as much as possible, but sometimes your intuition is much more powerful than the greatest performance dashboard in the world. In the first season of HBO’s monumental Mafia series The Sopranos, family patriarch Tony Soprano’s own mother tries to have him whacked. He had revealing dreams about this before it happened, but refused to look at the painful true meaning of these dreams. Through therapy, he learned to use his subconscious like a true expert, so when his friend Big Pussy Bonpensiero starts ratting for the FBI in season 2, he knows something is wrong. In a fever dream, Big Pussy (as a fish), reveals the hard truth to Tony. When he wakes up, he knows exactly what to do. Big Pussy must sleep with the fishes. Tony’s new ability to listen to his subconscious makes him a much more effective leader.

7. Think and act faster
Nucky Thompson
The Gangster: Nucky Thompson, Boardwalk Empire

The Lesson: After a botched assassination attempt on bootlegger and crooked politician Nucky Thompson, his enemies are left numb and indecisive of what to do next. Nucky – on the other hand – immediately makes a counter move. He goes to see his enemies and tells them the attempt on his life changed his perspective on things. He will abandon the bootlegging business and politics, so his enemies can take over. In secret however, Nucky books a trip to Ireland the next day, where he purchases a huge amount of cheap and highly qualitative Irish whiskey. His enemies underestimated him. By thinking and acting faster than his opponents, Nucky manages to surprise them and outperform them in business.

8. Take compliance seriously
Al Capone
The Gangster: Al Capone, The Untouchables

The Lesson: He was the king of his trade; the bootlegging business in Chicago. He made millions importing booze and selling it to bars and clubs. The thing that brought him down was income tax evasion. Managers can learn a simple truth from this mistake; compliance is your license to operate. Off course in Capone’s case this was a little different because he did not have any legal income to begin with, but many CEO’s of businesses have fallen into the same compliance trap. Sure, sometimes it is cheaper to pay a fine than to spend a fortune on meeting some obsolete policy, but you should never fail to answer to the most important rules and regulations. So even when it is sometimes tempting to bend the rules, in the end: being non-compliant is always more costly than being compliant.

9. Ride the Industry Waves
Tony Montana
The Gangster: Tony Montana, Scarface

The Lesson: Every industry has its waves, and a great CEO knows how to ride these waves. Take the drug business in the 1980’s. Cocaine was coming up big time in Florida. After Montana gets rid of his weak boss Frank, he sets up a massive cocaine trade in Miami and surroundings. His supply chain is very efficient. He imports the stuff straight from the source in Bolivia. Nobody can compete with that. It isn’t before long that Montana is Florida’s one and only cocaine king.

10. Keep your friends close and your enemies closer
Don Vito Corleone
The Gangster: Don Vito Corleone, The Godfather

The Lesson: You want to know what your competitors are up to? Invite them over for dinner and a meeting. Don Vito Corleone does it all the time. When he invites the heads of the five families for a sit down, in this powerful scene in The Godfather, he learns a great deal. It is not Tattaglia he should worry about, but that treacherous Barzini. Now that he understands the conspiracy against the Corleone family, he can help his son Michael take the necessary precautions.

Fear and Loathing in Las Vegas

Director: Terry Gilliam
Written by: Hunter S. Thompson (book), Terry Gilliam (screenplay), Tony Grisoni (screenplay), Tod Davies (screenplay), Alex Cox (screenplay)
Cast: Johnny Depp, Benicio Del Toro, lot’s of cameo’s including; Tobey Maguire, Gary Busey, Ellen Barkin, Christina Ricci, Cameron Diaz, Flea and Harry Dean Stanton

Year / Country: 1998, USA
Running Time: 118 mins.

It is the foul year of our lord 1971 and Gonzo journalist Hunter S. Thompson (Raoul Duke in the story) and his Samoan attorney Dr. Gonzo decide to undertake the ultimate trip of the seventies. The official assignment is to cover the Mint 400 desert race in Las Vegas, but they have something bigger in mind. They want to find the American dream. Armed to the teeth with highly dangerous narcotics, they head out to Las Vegas in their fire red convertible… Some trip it’s gonna be…

While searching for the American dream, Thompson and Dr. Gonzo only find fear and loathing. Intolerable vibrations in a town not at all suitable for the use of psychedelic drugs. The atmosphere is extremely menacing, but as they behave as animals, nobody even notices them. Vegas turns out to be a savage town. And while soldiers are dying in Vietnam, used car dealers from Dallas throw their money in the slot machines, Debbie Reynolds sings in the Desert Inn and the national police force meets at a congress about marijuana. Thompson and Dr. Gonzo are there.

Thompson’s novel ‘Fear and Loathing in Las Vegas’, which was first published in two parts in Rolling Stone Magazine, became a cultural phenomenon (and my personal favorite book of all time). The movie adaptation by Terry Gilliam is a literal one. Thompson wrote his famous novel Gonzo style, which means the events are told through the eyes and vision of the author who fully participates in the story himself. Since Thompson was heavily under the influence during the writing process, he claims he can’t fully remember which parts truly happened and which ones did not (fully). Therefore this literal adaptation is a highly enjoyable blast, though not always realistic.

There is one downside to director Gilliam’s literal approach. In the novel, all the psychedelic escapades form an integral part of what is obviously a literary masterpiece. In the translation to film however, these escapades sometimes appear to be useless fuckarounds, especially during the final part of the film. However, that is a minor criticism for this is obviously a highly enjoyable movie. Depp and Del Toro are both terrific in their method acting approaches to their roles. Thompson’s poetic writing, beautifully narrated by Depp in voice-over, runs through the movie that captures the era and hallucinogenic nightmare perfectly. Combined with a beautiful seventies soundtrack and Grade A settings, the great time capsule that is Fear and Loathing in Las Vegas is complete. Also, it is one of the funniest movies of all time. So buy the ticket and take the ride.

Rating:

Biography: Terry Gilliam (1940, Minneapolis) started his career as the only American member of the British comedy group Monty Python. As animator, he was responsible for the bizarre cartoons used in the sketches. In 1975 he directed his first movie for Monty Python, namely Monty Python and the Holy Grail. After his period with Monty Python, he moved on as independent director and had remarkable success with his bizarre masterpiece Brazil in 1985. After that success, things went downhill for Gilliam; The Adventures of Baron Munchausen became an expensive flop and the disastrous production of the never completed Don Quichotte became legendary. Despite these problems, Gilliam returned and directed a number of valuable contributions to cinema, including sci-fi masterpiece Twelve Monkeys and cult classic Fear and Loathing in Las Vegas.

Filmography: Storytime (1968, short) / The Miracle of Flight (1974, short) / Monty Python and the Holy Grail (1975) / Jabberwocky (1977) / Time Bandits (1981) / The Crimson Permanent Assurance (1983, short) / The Adventures of Baron Munchausen (1988) / The Fisher King (1991) / Twelve Monkeys (1995) / Fear and Loathing in Las Vegas (1998) / The Brothers Grimm (2005) / Tideland (2005) / The Imaginarium of Doctor Parnassus (2009) / The Legend of Hallowdega (2010, short) / The Wholly Family (2011, short) / The Zero Theorem (2013) / The Man Who Killed Don Quixote (2018)

The Rum Diary



Director:
Bruce Robinson
Written by: Bruce Robinson (screenplay), Hunter S. Thompson (novel)
Cast: Johnny Depp, Amber Heard, Michael Rispoli, Aaron Eckhart

Year / Country: 2011, USA
Running Time: 115 mins.

The title ‘The Rum Diary’ can mean two things. Hunter S Thompson’s novel that is told in this movie or The San Juan Star, the near bankrupt Puerto Rican newspaper where main character Paul Kemp (Thompson’s alter ego) takes a job as journalist. Why? Because the entire writing staff is completely drunk. The same seems to apply for the whole population of Puerto Rico in the 1960’s, the setting of The Rum Diary.

This is a story about alcohol and lots of it. But, whenever Kemp takes time off of drinking, he engages in a compelling journalistic endeavor, shining light on the culture and problems of the relatively unknown country he resides in. This is also a love story. Kemp falls head over heels for the stunning Chenault, the girlfriend of corrupt businessman Sanderson, who wants Kemp to write stories in favor of his unethical real estate plans.

Kemp’s dilemma, going along with the flow or exposing the ‘bastards’ as he puts it, is the backbone of this movie. The pace is as relaxed as the setting and director Robinson succeeds well in translating the mood of Thompson’s novel to the white screen. The cast is on a roll as well. Depp, who once said he would like to play Thompson every few years, is solid as always. He gets excellent comic support from press associates Michael Rispoli, Richard Jenkins and Giovanni Ribisi. Amber Heard and Aaron Eckhart play Chenault and Sanderson, whose characters add the necessary intrigue and substance to the story.

Obviously this is no Fear and Loathing in Las Vegas and the drug fuelled craziness portrayed in that movie is largely absent. This is Thompson Light; a smaller movie without too much excessive behavior. Director Robinson did add one pretty funny drug scene that can be considered as a wink to big brother Fear and Loathing. In The Rum Diary, the author Thompson is still searching for his unique voice and it is pleasant to join him on this quest. It is best to keep some rum within reach though as you might get thirsty underway.

Rating:

Biography: Bruce Robinson (1946, Broadstairs, Kent) started his career as an actor, but did not find it fulfilling nor lucrative. He started writing screenplays and in 1984, his Cambodia script The Killing Fields was turned into a memorable war movie by Roland Joffé. With his second script, he chose to direct himself. Withnail & I, which is largely autobiographical, became a cult classic. Robinson’s subsequent films, the advertising satire How To Get Ahead in Advertising and the serial-killer thriller Jennifer 8, while less memorable than his debut, still showed Robinson’s talents. In 2011 he brought The Rum Diary, a novel by legendary writer and Gonzo journalist Hunter S. Thompson, to the screen which received mixed reviews.

Filmography: Withnail & I (1987) / How to Get Ahead in Advertising (1989) / Jennifer Eight (1992) / The Rum Diary (2011)

Maniac Cop

Director: William Lustig
Written by: Larry Cohen
Cast: Tom Atkins, Bruce Campbell, Laurene Landon

Year / Country: 1988, USA
Running Time: 85 mins.

In the eighties many, many (perhaps too many) slasher movies saw the light of day, trying to profit from the popularity of genre classics such as Halloween (1978) and Friday the 13th (1980). Many lacked the true passion for the art of exploitation filmmaking though and were merely cash-ins. This can not be said about Maniac Cop, because two inspired exploitation film makers are behind it. Larry Cohen produced and wrote the screenplay and William Lustig directed. Cohen was at the time mostly known as director of blaxploitation flicks Black Caesar and Hell Up in Harlem and the It’s Alive horror trilogy, while Lustig made the controversial Maniac in 1980.

The potential for a real cult treat was certainly there. Besides Cohen and Lustig, the cast had Bruce Campbell and Richard Roundtree in it, enough to make cult fans drool. The concept is also promising: police brutality offers plenty of opportunity for both humour and scares. The poster and tagline really sell this flick: ‘You have the right to remain silent. Forever!’ Great!!! Let’s watch this.

Unfortunately the execution of Maniac Cop is disappointing. As much as I wanted to enjoy this, it fell short on delivery. The positive critique is that the suspense is adequately delivered. The story is what you would expect it to be. A six foot tall cop is killing innocent people in New York and panic spreads through the city. Bruce Campbell’s cop Jack Forrest is wrongfully accused of the killings and he and a few accomplices have to discover the (supernatural) truth and stop the killer.

Why it is disappointing, is mostly because so much potential is wasted. There are no moments in which the police brutality angle is put to good use. There is hardly any humour in the movie and when you have Campbell in your cast that is a deadly sin. The action-packed finale of the film also fails to offer a satisfactory conclusion.

Perhaps part 2, which is said to be Lustig’s favourite entry in the trilogy, has more to offer. The third instalment Maniac Cop 3: Badge of Silence (1993) is best left alone though. When voodoo comes into play, it won’t do much good to this concept.

Rating:

Biography: William Lustig (1955, New York) always enjoyed exploitation flicks and wanted to pursue a career as filmmaker. After working as assistant on a few films, including Michael Winner’s Death Wish, he directed two porn movies under the alias Billy Bagg. In 1980, Lustig found himself at the center of a storm of controversy when he made the disturbing slasher film Maniac. Throughout the eighties and nineties he would continue to make exploitation films, including the Maniac Cop trilogy.

Filmography: Maniac (1980), Vigilante (1983), Maniac Cop (1988), Hit List (1989), Relentless (1989), Maniac Cop 2 (1990), Maniac Cop 3: Badge of Silence (1993), The Expert (1995), Uncle Sam (1996), Conducting Dario Argento’s ‘Opera’ (2011, short doc)