Where Mafia Villains Find Redemption: The Big Screen

I wrote my last name on the high school registration list – it happens to have more vowels than most. The older students in line behind me whispered, “Watch yourself around this fuckin’ guy” and “He’ll sic the teamsters on ya.” Turns out my last name is but a vowel away from one of Detroit’s most famous attorney’s, who also happened to represent Jimmy Hoffa for 25 years. Fairly or unfairly, one of Detroit’s most prominent families was branded Mafia. Society never seemed bothered either way, complements of a century of Hollywood romanticizing the American Mafia.

When I turned around to see what was up, the guys looked at their shoes. I noticed one of them had a broken arm. I don’t know the story behind his story, but I got the gist because I felt the power. I felt their fear. I felt like I could do whatever I pleased, and they wouldn’t stop me. They thought I was someone I wasn’t, the random spawn of a reputed Mafia boss. Had anyone asked me at that moment if I wanted to join the Mafia myself, no question I would have jumped at the chance. I was sure the guy with the dangerously similar surname got all the girls.

Key Largo movie

Hollywood’s Open Marriage to the Mob

From that moment forward, I studied the way kids do – by watching mob movies, which all seemed to contain a kernel of truth. From classics like Humphrey Bogart’s The Big Heat, Dark City with Charlton Heston, and just about every movie James Cagney starred in – they all seemed to involve la cosa nostra in one way or another (especially White Heat). Sometimes they were the protagonists, sometimes they were unforgiveable shitheels. Even when they came to a bad end, they were memorialized and redeemed for the movie screen.

Hollywood has romanticized the Mafia beyond all recognition. From Vito Corleone to Tony Soprano, fact and fiction have become blended. Oddly enough, Scarface himself, Al Capone, called the mob movie genre “terrible kid’s stuff.”^[1] But the same Volstead Act that made him the most famous bootlegger, also confirmed the marriage of Hollywood to the Mafia.

The money in bootlegging and manufacturing bathtub-style hootch was legendary. The prolific bootlegger who built the mold for the Hollywood Mafia marriage was Joseph Kennedy. In fact, he made his second fortune in bootlegging. (His first fortune came from stocks). While he earned several fortunes over his lifetime, his investment in Hollywood was probably the most farsighted and impactful.^[2] The Kennedy family patriarch’s foray into film gave the future political family the financial backing to grow a political dynasty and run on their morals. Ironically, when appointed by his brother to become Attorney General, the first thing RFK did was go after the Mafia.^[3]

Godfather movie

Growing Pains

When Prohibition came to an end, the Mafia found itself in the position of protecting immigrant communities and labor unions, for a price. They worked for corrupt politicians by forcing citizens to go vote for their candidate. They purchased legitimate businesses adjacent (or extorted them from a patsy) to the entertainment world like bars, restaurants, night clubs, and casinos. (Yes, a strip club counts as a business.) Even low-rent mobsters used their Hollywood connections to become the agents for actors and musicians, while extracting an unusually high percentage usually not worth their services. In the greater scheme of things, while they promoted new acts, they built audiences for jazz and pop music entertainment just as the radio era was turning the page to television.

Sinatra’s Rat Pack

Think of all the amazing acts we would have missed minus the influence of the Mafia! Frank Sinatra, Sammy Davis Jr., Dean Martin, Frankie Valli, Marilyn Monroe, Marlon Brando, McGuire Sisters, Joe Bonanno Jr., and “Big” Paul Castellano; had their careers facilitated through mob influence in the entertainment industry. Just to name a few. Even Madonna has family connections!^[4] [Editor’s note: as reported in numerous media stories, biographies, and movies.]

Bugsy movie

The Movie Mafia

In the movies, the mobsters lived life in color. They were fearless. They were rebels fighting an unjust system. They always had a wad of cash (the forefather of today’s “gangster roll”). They didn’t pay taxes. They were modern American Robin Hood’s stealing from the corrupt and giving the poor a taste of the good life in the form of fugazi mink coats, discount generic cigarettes, and very, very high interest loans. There were rarely consequences to their actions. They wore slick threads, drove fast cars, and had a girl for every day of the weekend. What’s not for a 13-year-old freshman to love?

Marilyn Monroe

After The Godfather debuted, film companies couldn’t get enough mafia stories. They received an embarrassment of riches from Martin Scorsese and company – Francis Ford Coppola and Brian De Palma. My friends and I knew Goodfella’s by heart. We watched The Godfather films countless times and always concurred that number two was the best. As we came up, the movies kept coming too: A Bronx Tale, Donnie Brasco, The Departed, The Irishman, Casino, Bugsy, Hoffa, Gotti. Forgive me for not listing all the deserving films here. Blame the strict word limit. Check out: the Top 100 Gangster Movies of All Time.^[5]

Things in real life, on the other hand, were very different.

The Mafia Colluded with Uncle Sam

From World War II to Goodfella’s-times (50’s-60’s), the Mafia held sway over world events. From 1942 – 1945 the U.S. Navy partnered with both the Italian and Jewish mafias to guard ports and factories from Brooklyn up to New England. Some wiseguys even worked undercover in the consulates of Axis powers as spies (such as Lucky Luciano).^[6] Even the most violent mob henchman could find his patriotism when the boss ordered. But things were never as they seemed.

There is only one documented instance when the U.S. government went to the Mafia for an assist. The target was Cuba’s communist dictator, Fidel Castro. CIA master spook Allen Dulles wanted Castro to be sleeping with the fishes sooner-than-later. So did the Mafia, who still had their panties in a twist over Castro shutting down their Havana casinos. “Through a middleman, an ex-C.I.A. employee enlisted organized crime leaders, including Sam Giancana and John Roselli, to work with the CIA to assassinate Castro. Spoiler alert: they failed. Numerous times.”^[7]

As far as the Feds were concerned, the mafia was batting .500, which was bukku bang for your buck in government circles. Job number three was a doozy and many of the facts remain murky. Whether the Mafia were behind the John F. Kennedy assassination is still a very classified matter. The fact is, Kennedy is dead. Someone killed him. The CIA doesn’t even believe their own Oswald as the stoolpigeon hogwash. The Oliver Stone movie JFK does a masterful job of looping Hollywood Gangster Mickey Cohen into the JFK assassination.^[8] Post assassination, Lee Harvey Oswald was framed as his killer. “Even then, the CIA knew he would be a bad fit for this suit.”^[9] The not-so-dynamic-duo finally solved the Oswald imbroglio with another sloppy assassination. The trigger man was Chicago nightclub operator Jack Ruby. He was widely known to associate with Chicago’s underworld figures. Infer away.

JFK movie

Day of the Rat

Rewatching Goodfella’s during a bout with COVID, I noted not just the size and scope of their crimes, but the publicity they received back then. Because of their audacity. Namely for the Lufthansa heist where almost $6 million in cash was stolen. In real life, the heist was masterminded by James Burke, an associate of the Lucchese family, but “remains otherwise unsolved today.”^[10] Whatever that means. The story was broadcast worldwide at the time and lives on in the lore of Mafia soldiers celebrating about the good old days. Either way, moving into the seventies, shit was changing fast for wiseguys.

This is the decade the shine came off public enemy number one. The news was out. Despite the glitz and glamour, there was also the blood and gore, the ruined lives, the trauma that would pass down through future generations. The murders and broken homes. Kids orphaned. Businesses burnt down to the studs. The corruption that destroyed everything in the name of pure avarice. In 1970, the Racketeer Influenced and Corrupt Organizations Act^[11] was passed. RICO was now the law of the land, which made prosecuting mafia organizations a much simpler process. Famed New York City prosecutor Rudy Guiliani successfully used the Act to prosecute the heads of all of New York’s major crime families and associated villains, henchmen, soldiers, and toadies. The blow nearly knocked the Mafia down for the count.

John Gotti, boss of the Gambino crime family, New York

But Nature Abhors a Vacuum

Enter the competition. MS-13 originated in Los Angeles but practically owns El Salvador by now. They traffic drugs, currency, women, and children. Men are sold as slaves or forced to fight under the gang’s colors. They produce Fentanyl by the tanker truck. They grow heroin where suburbs should have been. The most of the old school Italians weren’t interested in the drug business. In an unspoken Catholic way, they saw drugs as the Devil’s gate to corrupt souls. When MS-13 moved in on their territories, the Mafia was outmanned and outgunned. They let their drug business slide. They didn’t want the war that would surely come their way. Instead, they maintained the other staples of their criminal portfolio – racketeering, protection, extortion, loan sharking, numbers, union organizing (or busting), entertainment, money laundering, counterfeiting, weapons dealing, prostitution, and assorted entrepreneurial schemes.

Sopranos TV Show

The opportunity cost for the Italians was staggering. Missing out on the drugs business in the ‘70s and ‘80s was like Thomas Jefferson turning down the Louisiana Purchase. Suddenly, the upstarts had all the cash and all the guns and all the connections. To survive, they had to adapt, which they managed to do by involving themselves in gambling, construction, real estate, pornography, trucking and distribution, movies, the music business, and, yes, waste management. When the new generation of Mafia started, they dove into the flourishing drug trade or computer crimes. These minor dons convinced the world that they were people too. What juror would vote against you if, say, there were pictures in the paper of you with Liza Minelli. Dinner with DeNiro wouldn’t hurt. Karaoke with Madonna for your kid’s birthday?^[12] Fuhgeddaboudit. The Mafia could do anything with an assist from Hollywood. Like the Rat Pack in the ‘50s, movies make monster mobsters into teddy bears. That, incidentally, is the origin of the expression “Hollywood make-over.”^[13]

Mafia 3.0

Traditionally, when you think Mafia, you think Italian or Sicilian. (Yes, they are two different places. Get a map.) But then the computer age arrived, and a new class of crime and perpetrator debuted – computer crimes and maestro hackers, respectively. The younger gangs were hip to the money that could be made phishing, stealing identities, SIM swapping, as well as sending malware.^[14] Was Ransomware the new “protection money?”^[15] Only your hostage laptop knows for sure.

Where Are They Now?

The power of the mafia in the Northeastern and Midwestern United States peaked in the 1950’s.^[16] Right about the time Nicholas Pileggi was living the good life as Henry Hill in Goodfella’s. The moral of the movie comes at the end, once Hill turns states evidence and leaves the Mafia in exchange for his life. His life was flipped upside down or, from the horse’s mouth, “Everything was all for the taking. And now it’s all over. And that’s the hardest part. Today everything is different. There’s no action. I have to wait around like everyone else. I can’t even get decent food…I’m an average nobody. I get to live the rest of my life like a schnook.^[17]

Since the “good old days” in New York, the mob has kept its fingers in gambling, corrupting public officials, loansharking, racketeering, exploiting legitimate businesses, and stock schemes.^[18] While I’m sure all of these were quite profitable, they’re not nearly as legendary as robbing an airport.

Due to the legalization of gambling in 48 states, my theory is that the Mob went mostly mainstream. Legit, as they say. Why live life looking over your shoulder when you could make mad money without the risk of prison? Between cryptocurrency and NFTs alone, suckers were born every tenth of a millisecond. When the money vanished, market forces were to blame. Not some guy named Paulie who yanks out fingernails for a living.

Donnie Brasco movie

1. https://lastmovieoutpost.com/hollywood-history-the-mob-and-tinseltown/ ↑
2. https://en.wikipedia.org/wiki/Joseph_P._Kennedy_Sr. ↑
3. https://lisawallerrogers.com/2024/05/09/robert-kennedy-goes-after-the-mafia/ ↑
4. https://radaronline.com/p/hollywood-stars-with-ties-to-the-mafia-robert-de-niro-madonna/ ↑
5. https://www.imdb.com/list/ls001818278/ ↑
6. https://nypost.com/2022/12/23/how-the-navy-made-a-secret-deal-with-the-mafia-to-win-wwii/ ↑
7. https://www.nytimes.com/2024/08/09/arts/television/mafia-spies-cia-kill-castro.html ↑
8. https://laist.com/shows/airtalk/hollywoods-celebrity-gangster ↑
9. https://www.cia.gov/readingroom/document/cia-rdp88-01315r000300510116-8 ↑
10. https://en.wikipedia.org/wiki/Lufthansa_heist&sclient=gws-wiz-serp ↑
11. https://en.wikipedia.org/wiki/Racketeer_Influenced_and_Corrupt_Organizations_Act#:~:text=During%20the%201980s%20and%20the,figures%20in%20United%20States%20v. ↑
12. Ibid ↑
13. Just messing with you! ↑
14. https://www.vice.com/en/article/how-the-mafia-is-pivoting-to-cybercrime/ ↑
15. https://www.forbes.com/sites/tonybradley/2015/10/16/cybercrime-is-the-modern-day-mafia/ ↑
16. https://en.wikipedia.org/wiki/Five_Families#:~:text=The%20five%20Mafia%20families%20in,This%20effect%20compounded%20over%20time. ↑
17. Goodfella’s, Henry Hill’s last line in the movie ↑
18. https://en.wikipedia.org/wiki/American_Mafia#:~:text=In%20the%2021st%20century%2C%20the,schemes%20and%20stock%20manipulation%20schemes. ↑