The Era of the Gangster Begins

In January of 1920, the passage of the Volstead Act made the production and distribution of “intoxicating beverages,” that contained more than 0.5% alcohol, illegal in the United States. The era of Prohibition had begun, but as an unintended consequence, so did the era of the gangster.

The illegal alcohol market allowed organized crime to gain levels of prosperity and social prominence that it had never before attained.

Massive illegal distilleries covertly produced vast quantities of illicit alcohol, and complex networks of smuggling operations moved truckloads of booze from Canada into northern U.S. cities before continuing down south. Underground bars, called speakeasies, were built all throughout the United States as distribution centers. This black market quickly began to generate millions of dollars each year. Like any big sector of the economy, the successful and powerful companies, in this case gangs and mafias, began to emerge as industry leaders, and the men who were able to lead these enterprises became famously rich.

The financial success of high-ranking mobsters made them infamous and a dangerous, yet captivating, part of people’s daily lives. The exploits and profiles of these mobsters and gangsters would flood the newspapers and radio waves of the 1920s and 1930s. The public’s reaction to these high-profile crimes and criminals was not entirely negative. Many Americans did not care for prohibition laws and were dissatisfied with the socio-economic reality of the time. With gangsters openly defying the laws and undermining prohibition, they became a type of antihero, loved for breaking the law.

As celebrity gangsters began to rise to power, cars were becoming a normal and integral part of American society. The daily dependency on cars to travel to work and leisure activities created a strong car culture in America that still dominates today.

An aspect of this car culture was the celebrity car. Unlike the public mass transit systems of street cars and railroads, privately owned automobiles allowed for affluent people to turn the car into a statement not just of wealth but of importance. It mattered what car a movie star drove because it was a representation of the importance of that movie star in Hollywood.

Rudolph Valentino, best known for his roles in The Sheik and The Eagle, had his iconic 1924 Isotta-Fraschini Tipo 8A. Clara Bow, made famous from her role in Mantrap and Wings, owned a 1929 Rolls-Royce Phantom Tourer. The Duesenberg was a luxury car for the extremely rich, and had owners like Clark Gable, Marian Davies, Ginger Rogers, and Gary Cooper. Just as these movie stars needed the status symbol of a powerful and impressive car to convey importance, so did the celebrity gangster.

Background photo: Prohibition agents destroying barrels of alcohol, 1921 from the Chicago Daily News negatives collection, Chicago Historical Society. From Wikimedia Commons.

The Duesenberg Motor Company

The story of how the Model J Duesenberg became the car of high-profile gangsters begins with the Duesenberg Motor Company and its founder, Fredrick Duesenberg.

Fredrick Duesenberg (December 6, 1876 - July 26, 1932) emigrated with his family from Lippe, Germany to the United States when he was eight years old. He was soon considered an engineering prodigy. He never received any formal education in mechanics and had only a few years of public elementary school education in Des Moines, Iowa before dropping out of school to support his family. Yet despite this, Fredrick would go on to design and manufacture the prime luxury vehicles of his day. A passion for racing drove Fredrick to learn all he could about mechanics and design from firsthand experience.

Fredrick began his career designing, building, and selling bicycles and bicycle engines with his younger brother, August. His first races were with his own bicycles, setting two speed records for the two and three-mile events in 1898. Despite this success, Fredrick Duesenberg quit working at the bicycle shop in 1904 to become an auto mechanic for Thomas B. Jeffery & Company in Kenosha, Wisconsin. After less than a year with the company, Fredrick and August Duesenberg were hired to head the newly formed Mason Motor Company, which would be the catalyst for Frederick’s lifelong dream of building the most powerful engine in the world.

This allowed for the Duesenberg brothers to continue to develop newer engines and design faster cars. Some of these designs would be made into racing cars, a common practice for advertising automobiles. The Duesenberg brothers would soon enter their first car in the 1912 Indianapolis 500.

In 1916, Fredrick and August Duesenberg decided to go into business for themselves with the creation of the Duesenberg Motor Company in Elizabeth, New Jersey. Initially, the company designed and built engines. During World War I, the Duesenberg Motor Company hit a financial high point designing engines for airplanes and patrol boats. But for the Duesenberg brothers, the passion was always in auto racing. The brothers continued to design and develop racecars and in their spare time, achieved a high level of success in auto racing by racing the cars they designed.

The Duesenberg name became well known in auto racing when in 1924, Lora L. Corum became the first American to win the Indianapolis 500. He finished first with an average speed of 98.234 miles per hour in the Duesenberg Special. The Duesenberg name would continue to grow in fame in subsequent races at the Indianapolis 500. In 1925, Peter DePaolo piloted a Duesenberg to first place with an average speed of 101.127 miles per hour, setting an average speed record that would not be broken until 1932. Two years later, in 1927, George Souders won with a Duesenberg engine and chassis but with W.S. White’s racing team. This winning streak cemented the Duesenberg name in racing history.

With the success of their engine designs and the brand recognition from their race victories, the Duesenberg brothers planned to expand from designers to automobile producers. In 1920, the Duesenberg Model A was launched as the first passenger car created by the company. The performance of the Model A reflected the high-speed reputation associated with the name Duesenberg from their work with high-powered engines.

The Model A was the first American production car to feature hydraulic brakes, while other manufacturers were still using mechanical brakes. The hydraulic brakes were cheaper and could stop a car more efficiently than traditional mechanical brakes. The innovative straight-eight engine of the Model A produced 90 to 100 horsepower, which was more like that of a racecar than a typical passenger car at the time.

Despite its advanced design and features, the development of the Model A would be plagued with long delays and poor management leading to mediocre sales. Many of the delays were a result of Fredrick Duesenberg’s constant drive to improve and redesign the car. After five years of production and numerous redesigns, the Model A left the Duesenberg Motor Company without the necessary finances to design a newer model car. As time passed and the Duesenberg Motor Company did not create newer models, many of the features that made the Model A unique, such as the hydraulic brakes and the straight-eight valve engine, became industry standards.

The notoriety from its racing victories and its reputation for luxury, put the Duesenberg Motor Company on the radar of business magnet Errett Lobban “E.L.” Cord.

E.L. Cord owned hundreds of automotive and transportation companies. His vision was to expand his automobile empire into the luxury car market. With its brand-recognition and financial troubles, Cord was eager to buy the Duesenberg Motor Company. Cord would buy a controlling share of the company in 1926 and would act as the proprietor of the company. Once in charge, Cord changed the name of the company to Duesenberg Incorporated and officially removed August Duesenberg from the company, although he would remain closely involved in development until its closing.

Under Cord, Fredrick Duesenberg had one directive: to make the best car on the market at any expense. The car was to have the body of a luxury vehicle and the muscle of the racing cars Cord knew the Duesenberg Motor Company could produce. For Cord, this was to be the crowning jewel of his automotive empire. For the Duesenberg brothers, it was an opportunity to build a car free from restrictions and limitations. In 1928, after just two years of development, the Model J was born.

The Model J Duesenberg possessed a commanding presence and high-end performance that set it apart from the rest of the cars in its class, such as the Hispano-Suiza, Isotta Fraschini, Mercedes-Benz, and Rolls-Royce. The Model J featured a 420 cubic-inch V8 engine that could produce an unprecedented 265 horsepower. The Rolls-Royce Phantom II that was introduced the following year did not exceed 50 horsepower. The Model J had another selling point for potential buyers: each and every Model J was a uniquely designed machine with a custom body made to the customer's specifications.

When a customer purchased a Duesenberg, they purchased only the chassis and the engine. The body of the car and its finishings, like paint color, seat style, and coach design had to be purchased through a coach building department within the Duesenberg Motor Company or from another coachbuilder altogether. The Model J from the Miles Collier Collections had its body designed by the noted coachbuilder, LeBaron J Phaeton.

In 1928, the Model J’s chassis and engine sold for $8,500, which when adjusted for inflation exceeds $124,000. Comparatively, the most common car at the time, the Ford Model A, sold for $500, and the average yearly salary was about $1,490.

Background Photo: Duesenberg Family: Back (left to right): Lena, Minie and Amalia. Middle (left to right): Frederick and August. Front (left to right): Conrad Jr., Conradine, and Henry, circa 1886. From Wikimedia Commons.

The Barber

One high-profile gangster to own a Model J Duesenberg was Jake Factor, or how he was known in the criminal world, “The Barber.”

Jake “The Barber” Factor was born on October 8, 1892. With his older half-brother Max Factor, who later became known for his Hollywood makeovers and signature looks, Jake trained as an actual barber in Chicago, Illinois and worked at a small barber shop on Halsted Street. To make extra money to support his parents, Jake Factor also worked at the Morrison Hotel as a barber. The hotel was frequented by the rich and powerful, and Factor used his time there to make important contacts. It was during this time that he would become known as Jake “The Barber”, a name that would follow him for the rest of his life.

When exactly Factor began his extensive criminal career is not known, but in 1919 at the age of 27 he was indicted under a federal warrant for stock fraud.

Stock scams were a favorite of Factor. He would convince financiers to invest in worthless companies that he held stocks in, which would then artificially raise the price of the companies’ value, making a profit for Factor when he sold his share. Another con Factor engaged in was convincing investors to give him money under the guise he would invest it in the stock market, when instead he would pocket the money.

In 1923, Factor successfully executed a series of gold stock swindles in Canada and Rhodesia. He managed to legally retain the money from his scams by narrowly beating the charges brought against him in court. Factor could have retired a very rich man, but less than a year after his near arrest, he put in motion the plan that would successfully perpetrate the single largest stock scam in European history.

In late 1923, Factor convinced New York's master criminal, Arnold "the Brain" Rothstein, the gambling boss who fixed the 1919 World Series, to grant him an initial fund of $50,000 to begin his European scamming tour. Factor began in London, England in early 1924 by selling worthless penny stocks to gullible British investors with great success.

He created the Tyler Wilson and Company stock brokerage firm in 1925 to sell stocks in fabricated companies to the elite of English society. Not even the wealthiest people of English society were safe from his schemes, including members of the British royal family and the chief of Scotland Yard. In less than a year, Factor had managed to scam a grand total of $8 million, which adjusted for inflation is about $115 million.

Factor’s scams were able to affect so many people because many of the investors from the affluent English families did not want to admit that they had been conned by Factor. By the time the victims were willing to come forward, Factor had already fled to France.

In France, he created a crime syndicate to rig the tables at the Monte Carlo Casino, which took so much money from the casino that it “broke the bank”. Factor eventually snuck back into the United States through Mexico. While in the United States, Factor was tried and sentenced in absentia, a legal proceeding that allowed the European authorities to try Factor although he wasn’t present. Factor was sentenced to 24 years in English prison. But, Factor would never serve his sentence as he devised an imaginative, intrepid, and intense escape plan that rivaled his cons.

Once back in the United States, Factor returned to Chicago where he knew he was well above the law and had the support of the Chicago Outfit gang and Al Capone. While not an official member of the Chicago Outfit, Factor had many connections to the gang and had hired them for their services whenever he had trouble with other gangsters or law enforcement.

In 1933 to avoid extradition to Europe, he faked his own kidnapping with the help of Capone. After several months he was “found,” and he accused Roger “The Terrible” Touhy of the kidnapping. Touhy, at the time of the accusation, had a stranglehold on the illegal beer production market in Chicago and Capone had tried and failed several times to muscle Touhy out. This fictitious kidnapping, orchestrated by Factor, created a gang war that led to Touhy being arrested and sentenced on kidnapping charges. This was a huge benefit to Capone’s empire and a means of escaping extradition for Factor.

Background photo: New York Stock Exchange, 1908. From the Art and Picture Collection, The New York Public Library.

Factor was unable to go to England to be imprisoned for his stock exchange cons due to the numerous charges and amount of people involved in his “kidnapping”. He had to be in the United States due to the “kidnapping” and was able to escape prison for his European crimes. Touhy was eventually imprisoned for the “kidnapping” from 1934 to 1959. After 26 years he was released, only to be murdered by the Chicago Outfit a month later on the front porch of his sister’s house. On December 19, 1959, Factor was questioned by the FBI where he took and passed a lie-detector test about the murder of Touhy.

Jake “The Barber” Factor had escaped justice after committing the biggest stock scam in European history. Factor went back to conning people in the United States and was later imprisoned from 1939 to 1949 for mail fraud involving selling fraudulent whiskey receipts that totaled $10 million.

After his release from prison, he soon moved to Las Vegas, where in 1955 he took over the Stardust Hotel, which he then sold in 1962 for $7 million. During his tenure at the Stardust, he operated as the front man for the Chicago Outfit; hiding the criminal ties of the casino from the public while acting on the gang’s behalf. During this time, he also attempted to bail out notorious mobster Jimmy Hoffa from his real-estate financial problems in Florida.

According to John Touhy, the author of When Capone's Mob Murdered Roger Touhy: The Strange Case of "Jake the Barber" and the Kidnapping That Never Happened, Factor had scammed anywhere from $50-200 million throughout his life; how much of this money he was able to keep is unknown.

In 1939, Factor was found to have $479,093.27 to his name when being investigated for not paying taxes for the previous four years. When asked about the tax discrepancy, he claimed to not remember and the matter was eventually dropped.

During the height of his career, Factor was wealthy and powerful enough to pay $20,000 to own a 1930 Duesenberg Model J Murphy. The Model J Murphy had the same 420 cubic-inch straight-eight cylinder with double overhead cams, 4 valves per cylinder engine design, and hand-built chassis as a Model J Phaeton. What set the Model J Murphy apart was the designer of the body of the car, the Walter M. Murphy Company, which provided the body to approximately 25% of Model J Duesenbergs sold.

By 1964 Factor had, for the most part, left behind his life of crime and shortly after the sale of the Stardust Hotel he retired to Beverly Hills, California. Once Factor had some legitimate wealth, he became both politically and philanthropically motivated. Factor donated a significant amount of money to John F. Kennedy’s 1960 presidential campaign. In 1962 after an investigation led by Attorney General Robert Kennedy, Factor was scheduled to be deported but instead received a presidential pardon from John F. Kennedy.

Factor’s philanthropy primarily focused on low-income African-American neighborhoods in California. Factor grew up very poor with Polish heritage and was a part of a racial minority in 1890s Chicago, for which he was negatively judged. His nickname, “The Barber,” was an insult to Factor. It was a reminder of his poor upbringing and a way of implying that, despite all of his wealth, he wasn’t any better than his past. Factor would pay reporters not to refer to him as “The Barber” but the name never went away. Perhaps because of this, Factor spent a large portion of his fortune on helping a group of people who he perceived as being in a similar position.

In a declassified 1967 FBI report to the director of the bureau titled, “Possible Racial Violence: Major Urban Areas: Racial Matters,” agents recount an investigation into Factor’s charitable actions. The FBI might have been investigating the issue due to Factor’s past, or it might have been because of concerns over racial tensions in the United States, as the report begins with “the Problem of denying the Negroes equal opportunity in the past would be greater than anyone realized.” The report details the loss of $1 million in federal funds to low-income African-American communities of Los Angeles from budget cuts, which had been recuperated by Factor’s donation to the area in the form of a $1 million youth center.

In 1968, the FBI wrote a second confidential memo to the director of the bureau about Factor’s philanthropic works. This memo was focused on Factor’s financial involvement with a large boy’s summer camp for low-income African-American children in the Watts neighborhood of Los Angeles. Factor is quoted in this report saying that the racial conflicts of the time were an “indictment of white people and … we have failed to really do anything.”

Factor spent his retirement overseeing the construction of churches, gyms, parks, and low-cost housing in low-income African-American communities. When Jake Factor died, three United States senators, the mayor of Los Angeles, and several hundred members of these communities attended his funeral.

Factor was a beloved member of his community as a philanthropist, but his reputation as a criminal and gangster was ever in the forefront.

Background photo: Monte Carlo Casino, Monaco, circa 1900. From the Boston Public Library.

The Killer

The Model J Duesenberg marketed itself as the car for men of action. Owney Madden, another owner of a Model J, was a man who could kill as easily as breathing - and had the death toll to prove it. Not exactly the kind of action E.L. Cord’s marketing team had in mind, but nevertheless the Model J Duesenberg resonated as a symbol of strength and power with formidable gangsters like Madden.

Owen Madden was born in Leeds, England on December 18, 1891. His parents, Francis and Mary Madden, were immigrants from Ireland who moved to England to escape the Irish Potato Famine. After various textile factory jobs in England, Francis Madden died. Left with nothing, Mary Madden moved ten-year old Owen and his older brother to Hell’s Kitchen in New York City in 1902.

For two years, Owen, now called Owney, lived a crime-free life and sporadically attended St. Michael’s Parochial School on West 33rd Street. However, at age 12, Owney left home to join a gang to help support his family.

Two years after joining one of New York’s most violent gangs, the Gophers, Owney Madden committed his first of many murders. According to Madden, by the time he was 14, he had already killed a man by bashing the man’s head with a lead pipe and stealing $500 from his wallet. Within three years, Madden had killed an additional four people and became a prominent member of the Gophers.

The Gophers was a name given by the public to a conglomeration of several different Irish gangs which together controlled most of Manhattan at the time. They got their unusual name for their habit of hiding in cellars.

By reputation, the Gophers were known for brazen, brutal acts of violence, even going as far as mugging lone patrol men in the gang’s territories for their guns and uniforms. The Gophers’ income came primarily from extortion, pimping, mugging, and ballot-box stuffing.

Madden earned a place of importance in the gang when he gunned down a rival Italian gangster in the streets. Madden addressed the shocked onlookers, “Owney Madden, 10th Avenue” as a challenge for them to call the police and left the scene. Madden was never charged with the crime. It would be this instance of violence that finally cemented his leadership of the Gophers and his street name – The Killer. As their leader, he generated $200 a day, which adjusted for inflation is $2,500, from the Gopher’s protection rackets.

As leader of the Gophers, Madden quickly became a professional killer and gunman known for his expensive tastes, his violent temper, and his jealousy when it came to women. Owney Madden was married to Dorthey Rogers in 1911 and had a daughter that year named Margret Madden.

However, Owney Madden was a serial adulterer in his early years. Owney’s jealousy and propensity toward violence would culminate in the most infamous moment of his criminal career.

n February of 1912, Owney Madden boarded a street trolley to shoot a store clerk named William Henshaw for asking out one of the women with whom Madden was having an affair. Henshaw lived long enough from his gunshot wounds to identify Madden as the assailant, but the charges against Madden were dropped because despite the numerous witnesses, nobody would dare testify against a man known as “The Killer.” When the woman was asked by the police if Madden had shot Henshaw, she coldly replied, “That ain’t the guy what done it.”

Over the next three years, the Gophers reached the height of their power as Madden’s criminal empire began encroaching into rival territory, particularly that of the Hudson Dusters. In retaliation, Madden was ambushed and shot 11 times outside Arbor dance hall by three members of the Dusters on November 6, 1912.

According to the November 7 edition of The Sun, Madden went to the dance hall in pursuit of his then wife, Dorthey Rogers. According to the news article, Rogers had learned about the affair Owney was having when the news of Owney killing William Henshaw was published. She decided to exact revenge against her husband by going dancing in a club outside of Madden’s sphere of influence because she knew it would make him jealous. After several failed attempts to get a private audience with his wife outside the club, Madden was met with several rival gangsters and was shot.

During his stay in the hospital, it’s reported that Madden, with the bullets still lodged in his body, told the surgeon, “Git busy with the knife thing, doc.” Madden miraculously survived the attack and subsequent surgeries despite the 10% chance the doctors gave his survival. When the police asked Madden to identify his attackers, he refused stating, "Nothing doing. The boys'll get 'em. It's nobody's business but mine who put these slugs in me!" Within a week of his release from the hospital, several members of the Dusters were killed.

Background Photo: The Gopher Gang with Owney Madden located in the middle back row, leaning forward, circa 1910. From Wikipedia.

Two years later in 1914, Madden became involved in a dispute with Little Patsy Doyle, a prominent member of the Dusters, over a woman named Freda Horner. Madden promptly ambushed and killed Doyle over the dispute. But this time Madden would be convicted of murder and sentenced to 20 years in Sing Sing Prison in New York. Madden would ultimately only serve nine years of the sentence, but during his time in prison the Gophers had been muscled out of New York City and dismantled by the newer alcohol-focused gangs that formed with the start of Prohibition.

Once out of prison, Madden realized that he had to adapt to the new black market and began to rebuild his empire in Hell’s Kitchen. Madden would make it big in the bootlegging business when he was taken in as Big Bill Dwyer’s partner. William “Big Bill” Dwyer was the leader of a massive alcohol smuggling operation that illegally imported whiskey from Canada into American cities. Dwyer became impressed with Madden’s tenacity when Madden began hijacking Dwyer’s liquor shipments and instead of starting a gang war with Madden, Dwyer hired Madden to intimidate the competition.

At the height of his career, Madden would own over 20 legitimate nightclubs. One of which was the Cotton Club in New York City, the nightclub famous for launching the careers of many African-American entertainers like Duke Ellington, Langston Hughes, Louis Armstrong, and Fats Waller. Madden also launched the movie careers of Mae West and George Raft. Mae West, star of She Done Him Wrong and I’m No Angel, described Madden as “Sweet, but oh so vicious.” George Raft worked as a driver for the mafia where he would meet Madden. Madden would encourage and help Raft to pursue an acting career. Raft would go on to play the villain in the original 1932 Scarface.

It was during his Cotton Club years that Owney Madden purchased his brand-new 1930 Model J Duesenberg. Madden was known by his Duesenberg as Donald Miller writes in Supreme City: How Jazz Age Manhattan Gave Birth to Modern America, “Madden always carried a pocketful of nickels and would toss them to raggedly dressed kids who gathered around his highly polished Duesenberg, parked outside one of his clubs,” Miller writes. “To these street urchins, he was Uncle Owney, the big-hearted mobster.” The last known location of the Killer’s Duesenberg is that it is owned by a private collector in Lincoln, Nebraska.

The beginning of the end for Madden’s reign in New York would occur in 1932 when Madden murdered Vincent “Mad Dog” Coll when he attempted to extort Madden. For the Italian Crime Families, Madden had killed one man too many. Through their influence with New York City’s police department, the Italian Crime Families increased police pressure on Madden. By 1935, Madden realized that his time was up in New York, and he retired to Hot Springs, Arkansas.

Once there, he operated Hotel Arkansas, a spa by day and an illegal casino by night. This was a far cry from the massive networks of clubs and casinos he owned in New York. Over the 30 years of Madden’s operations, Hot Springs slowly became a hotspot for gangsters like Al Capone, Frank Costello, and Bugs Moran when they needed to hideout from the authorities. Charles “Lucky” Luciano was apprehended at Hotel Arkansas in 1935. Madden finally became a naturalized American citizen in 1953, and he eventually married Agnes Dempsy, the daughter of the city’s postmaster.

During his supposed retirement in Hot Springs, Madden became a local fixture of the town. He was easily recognizable with his iconic cap and scarf, and of course his 1930 Model J Duesenberg. Madden also became increasingly philanthropic in his later years, benefiting many local charities in Hot Springs. Among his many charitable endeavors was the purchase of school uniforms for the local high-school’s marching band members, one of whom was a young Bill Clinton. The majority of Madden’s efforts were focused towards youths, perhaps a byproduct of Madden’s own rough upbringing with the Gophers.

In 1961, a federal investigation by the Senate Committee on Organized Crime concluded that Hot Springs was the site of the largest illegal gambling operation in the United States. Madden was summoned before the Senate Committee on Organized Crime where he repeatedly invoked the Fifth Amendment. The Arkansas state government began cracking down on illegal gambling in 1964, and Madden’s empire was fading away for the third time in his life.

Before the crackdown took too much of a toll on Owney Madden’s empire, he died from emphysema on April 24, 1965. Owney “The Killer” Madden is buried in Greenwood Cemetery in Hot Springs next to his second wife Agnes Dempsy.

Background Photo: Hells Kitchen, New York City, circa 1890. From Wikimedia Commons.

Mickey Duffy

Another Duesenberg owner from the early 1900s was a man known simply as Michael “Mickey” Duffy. Not much is known about him due to his careful and meticulous nature. Nevertheless, the story of Mickey Duffy is reminiscent of the classic Hollywood gangster movie, with the rise and fall of a mob boss due to their greed and lust for power.

William Michael Cusick was born in 1888 to Polish immigrant parents in the Grays Ferry neighborhood of Philadelphia, Pennsylvania. Once he became involved with the Irish gangs of Philadelphia, he used a variety of Irish pseudonyms such as John Murphy and George McEwen, but he settled on Michael “Mickey” Duffy.

Duffy would only be arrested a few times for petty thefts and various misdemeanors. The only time he was ever convicted and sentenced would be in May of 1919 for assault and battery with intent to kill. After serving almost three years at the Eastern State Penitentiary in Philadelphia, Duffy was back on the streets and continued his climb up the criminal ladder.

Once Prohibition began in 1920, Duffy easily found a vast fortune in the world of booze smuggling, brewing, and illegal bar operations. He was clever enough to invest his illegal profits into legitimate business like the fashionable Club Cadix and the Ambassador Hotel in Atlantic City.

The gangster practice of owning legitimate businesses created a financial paper trail that would ward off federal investigators. Duffy was exceptionally good at creating paper trails, given that he would never be charged with another crime for the rest of his life. His ability to appear legitimate gave him the edge over his competition that was needed to turn Philadelphia and the surrounding cities into his illegal booze kingdom.

Duffy’s rise to power was largely due to the misfortunes of other gangsters. His biggest competition in his early years was Max “Boo Boo” Hoff, who lacked Duffy’s keen ability to conceal his criminal activities. Hoff and his organization were recuperating from numerous federal investigations, raids, indictments, and property seizures. This allowed Duffy the opportunity to covertly take over all of Hoff’s territory and breweries.

Additionally, Duffy never killed publicly and maintained a relatively low profile on his criminal activities when compared to other well-known gangsters. He was constantly trying to seize smaller gangsters’ territories primarily through intimidation and not murder, although murder was never truly off the table. When it came time for Duffy to take over another gangster’s territory, fewer people tended to die than other more famous gang wars, which allowed Duffy to be able to take territory quickly without losing money or manpower. Duffy’s practices led his gang to grow extremely large, so they were able to generate millions of dollars in illegal profits with few significant obstacles.

Background Photo: Philadelphia, Pennsylvania, circa 1930-1945. From Wikimedia Commons.

Mickey Duffy’s success created a unique situation where he always had enemies but never any true rivals. Of his many enemies, the Bailey Brothers would be the first of many to try to kill Duffy. On February 25, 1927, Duffy and his bodyguard John Bricker, were ambushed on their way out of Club Cadix by associates of the Bailey Brothers. The brothers had acquired a Thompson submachine gun or “Tommy Gun” from Duffy’s rival, Boo Boo Hoff. Duffy survived but his bodyguard did not. Bricker would become the first man killed in a gang shooting by a machine gun in the United States. Duffy was seriously injured after being shot multiple times and was not expected to survive, but he recovered and within weeks was back to building his criminal empire.

Duffy had created an impressive fortune from his bootlegging operations and his illegal speakeasy bars during Prohibition. He regularly stayed in luxurious suites at the Ritz Carlton in Philadelphia, the Walt Whitman Hotel in Camden, and in his own luxury hotel, the Ambassador Hotel in Atlantic City. He also owned a $90,000 mansion ($1,318,663.16 adjusted for inflation) with his wife, Edith, a former hat check girl, on City Avenue in Philadelphia. His wife was known to wear a $30,000 diamond bracelet at any public event to show off their wealth.

But above all, his prized possession was his 1931 Model J Duesenberg that he bought brand new for $20,000. The exact location or even present existence of Mickey Duffy’s Duesenberg is not clear. The location of Duffy’s Model J may very well be lost to time. There is a claim from the Hemmings Daily article, Gangster-bought Duesenberg Model J/SJ heads to auction, published in 2013, that the car was up for sale but had not found a buyer. The biggest claim is that Duffy’s car went to Owney “The Killer” Madden after his death. This is extremely unlikely, as there is no evidence Madden and Duffy knew each other, and Madden’s car was a 1930 Model J Duesenberg and Duffy’s was a 1931.

Duffy’s downfall began on September 19, 1930 in Elizabeth, New Jersey; the very city his Model J Duesenberg was made. One of Duffy’s breweries was being raided by agents of the Bureau of Prohibition when Duffy’s enforcers arrived. The enforcers drew guns on the agents to intimidate them into leaving, but an altercation began between the enforcers and Prohibition Agent John Gilbert Finiello. During the shootout, Agent Finiello was shot and killed.

Later that same year, Mickey Duffy was dubbed “King of the Numbers Racket” due to his illegal lottery system by Philadelphia District Attorney John Monaghan. Duffy was also known for a brief time as Public Enemy Number One in Philadelphia, possibly due to the killing of Agent Finiello. Now in the spotlight of the authorities and other gangsters, Duffy did not have long to live.

On August 30, 1931, Mickey Duffy was asleep in a suite at the Ambassador Hotel in Atlantic City when an assassin(s) entered the room and shot and killed him. The perpetrators were never found and no charges were ever filed for Mickey Duffy’s murder. Speculation leads to the idea that Duffy was killed by members of his own gang to seize his power for themselves and to protect the rest of the gang from the threat of a federal crackdown due to Duffy’s growing infamy.

Despite his constant territorial fights with other gangsters, Mickey Duffy was well loved in Philadelphia. He was a major sponsor of his local church and the city’s orphaned children. Mickey and his wife were unable to have children, and their requests to adopt were denied. As a result, Duffy became a benefactor to various children’s programs in Philadelphia and to the low-income residents of the city.

Duffy was known to buy hundreds of tickets to sporting events and give them out to the low-income neighborhoods. After he recovered from his first assassination attempt outside Club Cadix, he donated $1,000 to the Hahneman Hospital and erected a memorial for his deceased bodyguard John Bricker, with the engraving, “Always to Be Remembered by Your Pal, M. J. D.”.

Duffy was an efficient gangster running Philadelphia’s underground, and it made him very wealthy; in return he gave generously and frequently to his city and the people in it. When he died, thousands of people attended his funeral.

Accompanying Duffy’s body to Mt. Moriah Cemetery in Philadelphia was a 31-car procession. One of the cars in the procession was his own Model J Duesenberg, which he had owned for less than a year. Duffy was found to have only $7,000 to his name, but he was reportedly buried in an expensive solid bronze coffin.

Background Photo: Police officer standing alongside wrecked car and cases of moonshine liquor, November 16, 1922. Courtesy of the Prints and Photographs Division, Library of Congress, Washington, D. C., from Wikimedia Commons.

Al Capone

Any list of infamous American gangsters begins with Al Capone. His brash bravado, acts of extreme violence, and flashy fashion, all of which were blatantly in the public eye, became what defined the gangster of the era. It is doubtful that any single person in American history can better capture the cult of personality or the celebrity of the mobster than Al Capone.

Alphonse Gabriel Capone was born on January 17, 1899 in Brooklyn, New York. His parents Gabriele and Teresa Capone were Italian immigrants from the province of Salerno in southern Italy. Gabriele, his father, was a barber and Teresa, his mother, was a seamstress. The Capone family lived in an apartment building without central heating, running hot water, or bathrooms. Al Capone quit school after the sixth grade and left his family to join a gang.

Capone bounced between several smalltime gangs until Johnny “The Fox” Torrio invited him to leave New York City for Chicago. Capone and Torrio were both members of the vicious Five Points Gang. When Torrio joined the Chicago Outfit, also known as the Chicago Mafia, and bought a club in Chicago, he offered Capone a job as a bouncer. Capone might have remained a low-level thug and lived a discreet life with his wife, Mae Coughlin, had it not been for Prohibition.

Once the black-market of alcohol took hold in Chicago, Capone was promoted by Torrio to move bootlegged whiskey from Canada to Chicago and in the process went from a small time criminal to a powerful force in the city’s underground. All the while, the authorities did little to nothing to stop the rise of the growing illicit market because they were either customers or were apathetic towards prohibition laws. Capone was able to gain favor with the authorities from a system of bribery and the ability to provide valuable illegal alcohol to the community. That favor would translate into special privileges for Capone from the corrupt police force.

Capone’s flaunting of the pass he had from legal consequences quickly became infamous. In August of 1922 after a night of drinking, Capone was racing his car along North Wabash Avenue in Chicago when he crashed into a parked taxi with the driver still in the car. Capone then jumped out of the car onto the sidewalk and in a drunken rage brandished a revolver and threatened to shoot the driver of the taxi and bystanders. “Alfred Caponi” was booked on three charges: assault with an automobile, driving while intoxicated, and carrying a concealed weapon.

In the official incident report, Capone was reported to be a deputy sheriff of Chicago. This undoubtedly was a bid by his gang, the Chicago Outfit, to get Capone out of legal trouble. Any one of the charges Capone faced would have sent an ordinary offender to prison, but like almost every case that was filed against Capone it did not even go to trial.

What many gangsters in the early illegal alcohol market quickly learned was that the chief problem to business was not the authorities, but the competition with rival gangs. Many of these gangs were comfortable with using extreme violence to remove their rivals. In Chicago, Capone would take part in multiple gang wars fueled by the desire for more sales territory and profit.

Of the many gang wars in the 1920s, none became as important to the gangster mythos as Capone’s war with the North Side Gang led by George “Bugs” Moran. This particular gang war would claim the lives of hundreds of gangsters, police officers, and civilians.

The Illinois Crime Survey by Arthur Lahly in 1930 reported, “In the period between 1920 and 1927 over four hundred gangsters had been killed by other gangsters and an additional two hundred had been killed by the police. A large number of policemen had also been killed in the war with these armed desperadoes. Some of the conflicts between rival gangs and between gangsters and policemen were carried on with machine guns firing from automobiles racing through the streets.” The gang war with the North Side Gang would continue until the dramatic final blow, the St. Valentine’s Day Massacre.

Background Photo: Map of Chicago's gangland, 1931. From Wikimedia Commons.

On February 14, 1929, two men in police officer uniforms arrived at a red brick warehouse at 2122 North Clark Street in Chicago at approximately ten in the morning. They entered the building and began to order the seven men currently inhabiting the building to line up with their palms against a wall. Most of these men were members of George “Bugs” Moran's Irish North Side Gang of Chicago.

Once all the men in the building were lined up against the wall, two additional men, not in uniform, arrived. The four men then proceeded to gun down Moran’s men with a combination of handgun and Thompson “Tommy” submachine gun fire.

The men who impersonated the police officers and their accomplices then successfully fled the scene before the actual police showed up. The men who were responsible were ultimately never found or charged.

However, it is widely suspected that the ordered hit on the warehouse was given by Al Capone who was in Miami Beach, Florida during the time of the attack. This mass murder would be dubbed the St. Valentine’s Day Massacre by the press and would make Capone the infamous celebrity he still is today.

To curb the violent reputation he received from the St. Valentine’s Day Massacre, Capone donated heavily to the poorest of the Chicago communities. During the Great Depression, this type of charity deeply impacted the people of these communities. In December 1931, the headline for the Chicago Tribune read, “120,000 meals are served by Capone Free Soup Kitchen.” Meals were served three times a day at 935 South State Street and it was made perfectly clear to the patrons from whose hand they were eating. People at the soup kitchen told the newspapers that Capone was doing more for the poor than the entire United States government, giving them not only food but jobs.

Capone had become so notorious in the United States that he was on the cover of the March 24, 1930 issue of Time magazine. In a bid to demonstrate a sense of control on the growing issue of organized crime, the federal government began to pursue a new charge in order to incriminate and jail notorious gangsters – tax evasion.

In 1929, Al Capone was charged with income tax evasion and would spend the next two years in an extensive legal battle that he couldn’t win. The tax evasion charge was successful because it was not a matter of witnesses or physical evidence that the mafia could just make disappear, it was purely a matter of paperwork and bureaucracy. There was no bribe that could be made or person to be intimidated, and Capone was livid.

The Daily News reported on the trial, “The 260-pound gang chief made no attempt to conceal his rage. He started forward as if to strike an Internal Revenue agent half his size when the agent presented him with liens attaching his property for overdue income taxes.” Capone was sentenced to eleven years in federal prison, fined $50,000 plus $7,692 for court costs, and was held liable for $215,000 plus interest due on his back taxes. The stiffest penalty ever meted out to a tax evader.

Once in prison, Capone’s health would quickly deteriorate, and his 18-year criminal career would abruptly end. Capone had contracted syphilis and, due to it going untreated, it developed into neurosyphilis soon after he was sentenced.

Capone was a serial womanizer and most likely contracted the disease from one of his many extramarital affairs. All his adult life he was known to keep various mistresses across the United States. One alleged mistress was Hollywood movie star, Gladys Walton.

John Walton, Gladys’ son, claims that Capone purchased a 1931 Model J Duesenberg for Gladys to better hide the affair that was taking place at the Two Bunch Palms Hotel in California, which was supposedly built for the specific purpose of hiding Capone’s affairs. The Duesenberg that Capone bought for Gladys was eventually passed to her son, John Walton who has had it restored.

After seven years, Capone was paroled from prison. Once released, Capone’s health, both physical and mental, would continue to weaken due to his neurosyphilis until his death in 1947. He was buried in Mount Olivet Cemetery in Chicago, but his remains were moved in 1950 to Hillside, Illinois.

Background Photo: Al Capone's house on Palm Island, Miami Beach, Florida, 1934. From the University of Miami Libraries.