Al “Scarface” Capone (1/17/1899-1/25/1947)
Capone made more money because of prohibition than anyone else by far. He was one of the founders of the Chicago Outfit an organization that still exists today. He came up under mentor Frankie Yale in New York. He was a lower level enforcer in New York but after moving to Chicago, he struck gold during prohibition.
A long and bloody battle for supremacy with the North Side Gang led to the St. Valentine’s Day Massacre in 1929. After that incident, Scarface became public enemy #1 and was soon locked up for tax evasion and would never see the streets again.
Arnold “The Brain” Rothstein (1/17/1882-11/5/1928)
He was the original boss of the American Jewish mafia. Rothstein was the man behind the infamous 1919 White Sox scandal where the players intentionally threw the World Series to get a payout from Rothstein.
The Brain was known as a gangster who elevated the level of the New York mafia. He was the mentor to many future mafia legends like Luciano and Lansky. Rothstein probably made more money from bootlegging than anyone besides Capone.
Frankie Yale (1/22/1893 - 7/1/1928)
Francesco Ioele aka Frankie Yale was an elite level gangster in the 1920s. Yale had some of the most notorious future mob bosses in his crew at the time: Al Capone, Joe Adonis and Albert Anastasia. He had his most trusted hitman Willie “Two Knife” Altierri who made a top level enforcer.
They battled with the White Hand Gang, a group of vicious Irish mobsters trying to resist the increasing Italian presence on New York organized crime. The problems for Yale started when he had a falling out with Capone, who had grown into a mob titan in the late 1920s. Capone’s gunmen caught Yale in 1928 and used a machine gun to do the job.
Giuseppe “Clutch Hand” Morello (5/2/1867 - 8/15/1930)
Giuseppe Morello was the boss of the very first mafia family in the United States, the Morello Gang. He was called Clutch Hand for his right hand which only had one finger and looked like a claw. The Morellos were active long before and through most of the prohibition era.
The Morellos faced fierce competition from the Camorra and several turncoats. Clutch Hand was murdered during the Castellammarese War in 1930, his murder has never been solved.
Joe “Joey A” Adonis (11/22/1902-11/26/1971)
Joe Adonis was the fastest rising star in the New York mob during the 1920s. It didn’t hurt that he was one of Lucky Luciano’s closest allies. Adonis had a brief working relationship with Al Capone when they were both under Frankie Yale in the early 1920s.
Adonis conspired with Luciano to kill Joe Masseria and Salvatore Maranzano, the two big bosses in New York. Joe Adonis went on to become a member of Luciano’s National Crime Syndicate until he was departed America in 1956, going back to Italy where he died in 1971.
William “Wild Bill” Lovett (7/15/1894 - 11/1/1923)
Wild Bill Lovett became the boss of the infamous White Hand Gang after the murder of original leader Dinny Meehan, which most historians pin on Lovett. He concentrated on extortion along the New York waterfront in the 1920s instead of entering the goldmine of prohibition.
Lovett and the White Hand Gang were a genuine threat to the influx of Italian mafiosi who were moving in on the docks. He killed many enemies and survived multiple attempts on his life before being killed by his own crew in 1923.
Charles “Lucky” Luciano (11/24/1897 - 1/26/1962)
Lucky built his early empire on bootlegging under the tutelage of Arnold “The Brain” Rothstein. He had an army of young peers like Meyer Lansky, Bugsy Siegel, Joe Adonis and Albert Anastasia who backed him in his rise to the top of the underworld.
Luciano secured the future of the American mafia when he created the Syndicate and the Commission. This helped the Italians corner the market on organized crime with their sophisticated structure.
Abe “Kid Twist” Reles (5/10/1906 - 11/12/1941)
Although he’s far more notorious for his time in Murder Inc., Abe “Kid Twist” Reles was also one of the countries’ most notorious killers going back to the early 1920s. He rose in the Brownsville Boys under the Shapiro brothers before the two sides fell out and Reles killed all three brothers. After prohibition ended, Reles joined Murder Inc., taking contracted hits directly from Lepke Buchalter and Albert Anastasia.
To get out of a murder rap, Reles became the first major mobster in American history to testify against the mafia. Albert Anastasia got the last laugh after Reles mysteriously fell out of a 6th story window, earning the nickname “The Canary Who Could Sing But Couldn’t Fly” forever.
Benjamin “Bugsy” Siegel (2/28/1906 - 6/20/1947)
He was considered a Hollywood style gangster from the beginning, good looking with an undeniable charisma and devilish charm. He was partners with Meyer Lansky and they created the infamous Bugs & Meyer Gang. They made millions on bootlegging before shifting smoothly to gambling and extortion after prohibition was repealed.
Unfortunately, after a failed stint running the Flamingo in Las Vegas, Siegel had blown millions of the mob’s money. Even his partner Meyer couldn’t save Bugsy, he was shot to death in 1947. Many suspect that his girlfriend Virginia Hill may have known about the plot and possibly even set Bugsy up.
Vincent “Mad Dog” Coll (7/20/1908 - 2/8/1932)
Of the many killers from this era, Mad Dog stands out as the most hated. He got his start an Irish hitman working for Jewish mob boss Dutch Schultz. They owned and ran speakeasies all over New York, making more money than the mob had ever seen. Coll outgrew his position and left Schultz on bad terms.
A war broke out leading to more than twenty men dead. What made Coll so despised was that in the midst of this war, Coll accidentally shot four children and killed a five year old boy. Less than a year later Schultz’s men caught up with Mad Dog Coll and put at least 15 bullets into him.
Arthur “Dutch Schultz” Flegenheimer (8/6/1901 - 10/24/1935)
Dutch Schultz had it all during the prohibition era. He was one of the richest bootleggers in the country and a member of the Syndicate. He then went into a bloody war with one of his renegade underlings, Vincent “Mad Dog” Coll. After many killings, Coll was blown away in 1932, ending that battle. He soon found himself in the crosshairs of federal prosecutor Thomas Dewey.
Schultz desperately wanted to kill Dewey but was overruled by the other Syndicate bosses. He lost his temper and vowed to kill Dewey regardless, and just days later he was ambushed and killed. Dewey simply adjusted his radar to the other Syndicate members afterward, which had them wondering if they should have just let Dutch do the job.
Johnny “The Fox” Torrio (1/20/1882 - 4/16/1957)
It was Johnny Torrio who groomed his protege Al Capone to take over the Chicago Outfit. He was considered very wise and respected by all in Chicago and New York. It was Torrio’s killing of Dion O’Banion that set the Outfit/Northside Gang war on fire. In 1925, Hymie Weiss, George “Bugs” Moran and Schemer Drucci ambushed Torrio, shooting him many times and then attempting to beat him to death.
Torrio somehow survived and refused to name his attackers even though he clearly knew. The incident only increased his respect in the eyes of fellow mobsters. He was ultimately allowed to retire in peace, dying of a heart attack.
Louis “Lepke” Buchalter (2/6/1897 - 3/4/1944)
Louis “Lepke” Buchalter was the boss of Murder Inc. in the 1930s and is currently the only mob boss to be executed in the United States. Lepke and his longtime partner Jacob “Gurrah” Shapiro got their start in the labor racketeering and bootlegging rackets under early Jewish mob boss Jacob “Little Augie” Orgen. Lepke and Gurrah killed Orgen in 1927 and took his territory.
It was around the end of prohibition era that Murder Inc. was created with Lepke and Albert Anastasia in charge. Lepke was a member of the Syndicate. Murder Inc. killed hundreds of people before hitman Abe Reles testified against his partners. His testimony put seven Murder Inc. members to the electric chair, including Lepke on March 4, 1944.
Albert Anastasia (9/26/1902 - 10/25/1957)
Albert got his start as a teenage brute working and fighting for respect as a longshoreman. He killed a man at 19 years old and got a death sentence, which was later overturned with the help of Lucky Luciano. Albert went back and took over the New York waterfront. He became Lucky’s top hitman and killed Joe Masseria in 1931.
He was charged with killing a man with an icepick in 1932 but the case was dismissed when all witnesses disappeared or died. Anastasia survived the fall of Murder Inc. and then killed his boss Vincent Mangano in 1951. The Lord High Executioner would face his own brutal execution while enjoying a shave at the Park Sheridan in 1957.
Jacob “Gurrah” Shapiro (5/5/1899 - 6/9/1947)
Gurrah and his friend Lepke Buchalter were criminal partners since their pre teen days robbing local pushcarts. They rose to become two of the biggest labor racketeers in the country after killing mob boss Jacob “Little Augie” Orgen and inheriting his rackets.
Gurrah was one of the founders of Murder Inc., the killing squad used as the enforcement arm of the Syndicate. The heat from prosecutor Thomas Dewey led to Gurrah’s downfall, he went to prison in 1938 and sat there until his death from a heart attack in 1947.
Salvatore Maranzano (7/31/1886 - 9/10/1931)
Maranzano was the early boss of what would later become the Bonanno Family. In 1930, he declared war on rival New York boss Joe “The Boss” Masseria, who was subsequently killed on April 15, 1931. Maranzano would be crowned boss of bosses but his reign would be short lived.
Lucky Luciano and other young mobsters felt like the day of the old world bosses needed to end, and Maranzano was himself killed just five months after Masseria. The New York mob was then sliced into five major families. Joe Bonanno was given Maranzano’s slice and the Bonanno Family was officially born in 1931.
Joe “The Boss” Masseria (1/17/1886 - 4/15/1931)
Joe the Boss is considered one of the last of the “Mustache Pete” style bosses. He used brute force and intimidation on his rise to the top of the New York mafia in the 1920s. First he took over the Morello Family and then he killed off his main rivals, the crew led by Toto D’Aquila which was then consolidated under Masseria.
He had a stable that included a young Lucky Luciano, Alfred Mineo, Steve Ferrigno as well as the Morello faction. Because they were in the midst of a huge gang war due to Masseria, Luciano decided to move in and he did in April 1931. Masseria was killed by Albert Anastasia, Vito Genovese, Bugsy Siegel and Joe Adonis.
George “Bugs” Moran (8/21/1893 - 2/25/1957)
Bugs Moran and the North Side Gang were the sworn enemies of Johnny Torrio, Al Capone and the Outfit. They were competing for the bootlegging profits in Chicago. The North Siders made multiple attempts on the lives of Capone and Torrio, who retired after being shot. At one time they truly had the Outfit on the ropes and Capone went into hiding.
After the murder of boss Hymie Weiss, Moran took over the North Side. The walls came crashing down on February 14, 1929, St. Valentine’s Day. Seven of Moran’s gang were murdered execution style and the North Side Gang basically disintegrated.
Charles “King” Solomon
Solomon was perhaps the first major mob boss in Boston. The Russian born Solomon built an empire on bootlegging, gambling rackets and even narcotics. When a conference of the countries’ top mob bosses was arranged in 1929, Solomon was invited along with Meyer Lansky, Johnny Torrio, Lucky Luciano, Frank Costello, Bugsy Siegel, Joe Adonis and many others.
He owned the Cocoanut Grove Nightclub which tragically burned down years later in 1942, killing 492 people. King Solomon was gunned down by rivals at the Cotton Club in 1933. Prohibition was gone in the same year so there was much less of his empire for his successor’s to grab.
Ciro “The Artichoke King” Terranova (7/20/1888 - 2/20/1938)
He rose through the ranks of the Morello Family, the first mafia family in America, under his half brother Clutch Hand Morello. They were experts bootleggers and “Black Hand” extortion artists. During the Castellammarese War, Ciro and future mob witness Joe Valachi were busy trying to kill each other.
Terranova was the driver who took Anastasia, Siegel, Genovese and Adonis to the Masseria hit. Ciro eventually was taken down mainly when the trading of artichokes was decriminalized and he lost the majority of his money. When he died of a stroke in February 1938, he was the only one of four brothers who didn’t get murdered.
Jacob “Little Augie” Orgen (January 1893 - 10/16/1927)
Little Augie was one of the first successful labor racketeers. By 1923, he had a stable of future mob heavyweights working for him: Lepke Buchalter, Jacob “Gurrah” Shapiro and Jack “Legs” Diamond. Together, they came to dominate the profits from the garment district.
The big problem for Orgen was that his ambitious lieutenants Lepke and Gurrah wanted what he had. On October 16, 1927, Orgen was killed and Diamond was shot, making the takeover official.
Willie “Two Knife” Altieri (unknown)
Frankie Yale had some fearsome men in his crew like future godfathers Al Capone and Albert Anastasia. During the mid 1920s it was Willie “Two Knife” Altiere whose name drew the most fear in enemies. Legend has it that he killed dozens of men. He got his nickname because of one particular gruesome murder.
Altiere always carried two knives attached to a leather waistband, legend is that he slept with the knives around his waist. After Yale was murdered, Two Knife disappeared and has never been seen again.
Richard “Peg Leg” Lonergan (1/16/1900 - 12/26/1925)
This brutal Irishman was a virtual nightmare for the Italian mafia. Peg Leg Lonergan got his nickname after losing his right leg after being struck by a trolley car. He became the final boss of the “White Hand Gang”, the rugged Irish crew that battled the Italians for bootlegging and waterfront supremacy in the 1920s after the murder of “Wild Bill” Lovett.
Peg Leg lasted two years as boss before he and his top two lieutenants were killed, at Joe Adonis’ social club of all places. It was Al Capone and some partners who killed Lonergan, Capone had a long standing rivalry against the White Hand, who quickly dissolved after the incident.
Abraham “Bo” Weinberg (1/7/1900 - 9/9/1935)
The ace enforcer for Dutch Schultz during prohibition was Abraham “Bo” Weinberg, a man suspected of killing Legs Diamond, Mad Dog Coll and Salvatore Maranzano among many others. Weinberg and the volatile Schultz had a falling out over power and Weinberg was hunted down in 1935 and made to disappear.
Bo’s brother George agreed to testify against Schultz and was put under 24 hour police guard. He was able to steal one of the detectives guns and instead of testifying, killed himself with the gun.
Vincent “Schemer” Drucci (1/1/1898 - 4/4/1927)
When Hymie Weiss was murdered in 1926, leadership of the North Side Gang was seized by Vincent “Schemer” Drucci. He proved to be more than a matchup for Capone and the Outfit. He made several attempts to kill Capone. The bullets were flying between the two gangs on a weekly basis.
Drucci and company nearly killed Johnny Torrio and ran him out of the mob. He was killed in April 1927, but not by Capone. Schemer is said to have grabbed for a policeman’s gun right before being shot to death, the only mob boss in American history to be killed by a police officer.
Owney “The Killer” Madden (12/18/1891 - 4/24/1965)
Owney Madden ran the bootlegging operations on the west side of Manhattan, in the neighborhood known as Hell’s Kitchen. He was a friend and mentor to famous Hollywood actor George Raft. Madden invested his money into nightclubs, like the Cotton Club and he Club Deluxe. He owned as many as twenty nightclubs and speakeasies.
He was involved with the murder of the despised renegade Irish mobster Mad Dog Coll. Madden continued to run Hell’s Kitchen until 1935 when he took off to Arizona with his money. He lived there while maintaining his mob ties under less scrutiny until his death in 1965.
Ignazio “Lupo the Wolf” Lupo (3/21/1877 - 1/13/1947)
The legend of “Lupo the Wolf dates back even before the 20th century. He came to America in 1899, escaping murder charges in his home land of Sicily. In New York, Lupo would team up with the Morello Gang to form the first mafia family in America. It was the addition of Lupo that made them a legitimate family.
He had his own crew in Little Italy and the two gangs consolidated for maximum power. Lupo is rumored to have killed as many as 60 people. Many of whom were stuffed into barrels and dumped on their neighborhood block as a message. When Luciano and the Syndicate took over, Lupo was looked at as a violent thuggish old “Mustache Pete’ and was exiled.
Fred “Killer” Burke (5/29/1893 - 7/10/1940)
Burke started out in a St. Louis gang known as Egan’s Rats. He graduated to another classic gang, the Purple Gang in Detroit. Burke got around in the 1920s, he and his crew specialized in good old fashioned armed robberies. Killer Burke was involved in a triple murder in 1927. After settling in Chicago Burke caught the attention of Outfit boss Al Capone.
Scarface decided to make Burke one of the men who dressed as police and rounded up seven members of the North Side Gang and executed them in the St. Valentine’s Day Massacre. He was later convicted of killing a cop and died of a heart attack in 1940.
Salvatore “Toto” D’Aquila (11/7/1873 - 10/10/1928)
Toto D’Aquila was a former captain in the Morello Crime Family who branched out to create his own family. He went to war with his old boss Giuseppe Morello. Toto had some heavy firepower in his crew, including Umberto Valente.
It was the supremely ambitious future boss Joe “The Boss” Masseria who killed Toto in 1928. The family legacy would live on and their lineage led to them becoming the Gambino Crime Family three decades later.
Jack “Legs” Diamond (7/10/1897 - 12/18/1931)
This was a case of a 9 lives gangster who used up all of them. Legs Diamond was a gangster who lived the Hollywood lifestyle, hanging out with celebrities and dating showgirls. He was a high ranking associate of Arnold “The Brain” Rothstein.
On the streets he was waging wars and dodging bullets. He was shot and wounded in 1927, 1930, and April 1931 in battles with the crew of Dutch Schultz. In December 1931 his luck would run out, Schultz’s men finished the job
Hymie Weiss (1/25/1898 - 10/11/1926)
Hymie Weiss of Chicago’s Norrth Side Gang was Al Capone and the Outfit’s most feared enemy. Weiss, Vincent “Schemer” Drucci and George “Bugs” Moran all were part of the gang under its’ original leader Dion O’Banion. Hymie took over as boss when O’Banion was killed in 1924 and quickly made the lives of Capone and Torrio miserable.
They weren’t able to go anywhere without worrying about being shot by the North Siders. During these days it looked like the North Side might win the war but then Weiss and Drucci were killed and the St. Valentine’s Day Massacre gutted the rest of the gang.
Frank Wallace (died 12/22/1931)
Frank Wallace was the boss of Boston’s first Irish mob crew, the Gustin Gang. Boston has a storied history of Irish mobsters over the last century and Wallace was the first big boss in the city. The Gustins made big money in the bootlegging business. They often supplemented their earnings with truck hijackings.
This was at a time when the Italians were quickly moving in and Wallace and crew became a target and was killed in 1931. It was the end of the Gustin Gang but the power of the Irish would remain in Boston.
Jack Dragna (4/18/1891 - 2/23/1956)
Mickey Mouse Mafia? Jack Dragna wasn’t exactly looked at as one of the most powerful mafia bosses in the country. Some New York bosses dubbed him the Head of the Mouseketeers, a swipe at his smaller army across the country in LA. What Dragna did was play his cards right. He managed to run bootlegging operations in an area that had less deadly competition.
Dragna emerged as boss before the end of prohibition in 1931 after killing Joseph “Iron Man” Ardizzone. His brother Tom and nephew Louis were also made members. Dragna would hold the top position for over 20 years before being deported and then dying of natural causes in 1956.
Abner “Longie” Zwillman (7/27/1904 - 2/27/1959)
Longie was a very successful Jewish bootlegger from New Jersey. He was known to have policemen, judges and politicians in his pockets and he paid them well for protection. He liked the Hollywood lifestyle and even dated the legendary actress Jean Harlow. When Dutch Schultz was killed in 1935, Zwillman took over his empire as well.
After slowing down in his later years he continued to be pursued by the government. He apparently hung himself in his home in February 1959 but many historians believe he was murdered
Dean “Dion” O’Banion (7/8/1892 - 11/10/1924)
O’Banion was the boss of Chicago’s North Side Gang, and he was universally loved and respected by his gang. It was a different story with Johnny Torrio and his top lieutenant Al Capone on the south side who were in a bloody war with O’Banion. The North Side was also waging war against the Genna brothers.
Bodies were being found in the streets on a daily basis. Capone enlisted some out of town help, Frankie Yale and “The Murder Twins” John Scalise and Albert Anselmi to kill O”Banion. They murdered O’Banion in his North Side flower shop. Hymie Weiss, Schemer Drucci and Bugs Moran would now lead the fight against Capone.