There is a reason why so many kids dress as gangsters during Halloween. Criminals have always fascinated us as a society and this is especially true when it comes to gangsters of the 20th century. They come from another time, a time when there was room to be lawless. Now that we are disconnected by nearly ahundred years its easy to look back and fantasize about the crooks, criminals, and bootleggers of yesteryear. We are taking a peek back in time to examine the guns of the gangsters, bank robbers, and mobsters.
Thank you for reading this post, don't forget to follow and signup for notifications!
Al Capone — M1911 Sweetheart
Al Capone was the mob boss in Chicago, and while he wasn’t part of the five families, he was famous for his bootlegging liquor empire. Al Capone’s most famous gun was a Colt M1911 he had customized and dressed to the nines. This M1911 has beautiful scrollwork and what appears to be stag horn grips.

The sights are larger for the era and appear to be adjustable. While the gun looks good, the sights showed that it would be a real shooter. His Sweetheart M1911 sold for over one million dollars at auction—fitting for a man who would be worth 18 billion if we accounted for inflation.
“Machine Gun” Jack McGurn — Thompson SMG
The Thompson could apply to any number of these men, but when your name is Machine Gun Jack McGurn, you earn the top spot for Thompson. McGurn was a prize fighter turned gangster in Capone’s organization. He was famous for the revenge killings of three hitmen who killed his stepfather. McGurn gained his name from not only his use of the Thompson but his control over the gun.

He used his favorite Thomspon to assassinate Hymie Weiss from an open window across the street from the rival gangster. McGurn later became a pro golfer, and accordingly, a Thompson was always in his golf bag, according to his caddie.
Jack ‘Legs’ Diamond — Luger
Jack “Legs” Diamond was an Irish gangster and bootlegger who dealt liquor throughout NYC and Philly. He became quite rich and dodged enough attempts on his life they called him the ‘clay pigeon of the underworld.’ The man had more lead in him than a Chinese lake. His gun of choice was, interestingly enough, the German Luger.

Specifically, a .30 Luger model, and he reportedly owned and used the famed 32-round snail drum for it. In that era, it was a lot of firepower for a pistol. The Luger was also lighter and likely easier to pocket, with less recoil than a 1911. Legs was known for being flamboyant, and he likely wanted something a little different than everyone else.
James “Whitey” Bulger — MP40
James “Whitey” Bulger is the man who almost got away. He started committing crimes in 1943 and had a very long criminal career. He wasn’t really busted until 2013 and lived to be 89 years old. He and the Winter Hill gang terrorized South Boston with an arsenal of weapons, but most impressively, this arsenal contained three MP-40 submachine guns.

The MP-40 was a German submachine gun used during World War 2. It was a 9mm, open bolt platform with an under-folding stock and an open bolt design. While Thompsons might have been common in the 1930s, the use of MP-40s in the 70s and 80s was rather rare. It likely offered Bulger a lot of firepower for his South Boston wars.
Bugsy Siegel — S&W Model 10
Bugsy Siegel built Vegas and the Las Vegas strip into what it is today. He was an influential gangster who founded Murder Inc, and his death is still a mystery. Not much is known about any preferences he had for firearms. Only one has ever been tied to him, and it was an S&W Model 10.

This .38 Special Revolver has been around since 1899 but obviously has changed and adapted with the times. It’s a simple double-action gun with six cylinders on a K Frame. They were extremely popular and likely best described as the Glocks of their day. It’s not a big surprise Siegel would have one.
Bonnie Parker — Remington Model 11 “Whippet Gun”
It’s not known if Bonnie Parker of Bonnie and Clyde fame ever fired a gun during the gang’s escapades, but an examination of their weaponry and photos lets us know she carried one. A famed photo of her pointing a shotgun at Clyde reveals the Remington Model 11, a copy of the Browning Auto 5. The gun had a sawn-off barrel and stock and was called a ‘whippet gun’ because you could whip it out from under a coat.

It’s notably a 20 gauge, semi-auto shotgun. That’s a small, light gun with minimal recoil. Bonnie Parker was the definition of petite, and this would have been a weapon that was a bit easier for her to tote and shoot.
Clyde Barrow — BAR “Scattergun”
Typically the term “scattergun” refers to a shotgun. However, Clyde Barrow nicknamed his BAR the scattergun. Why? According to him, when you pointed it out, people scattered. The BAR wielded by Clyde was stolen from the National Guard, and he sawed off the barrel and gas tube to make it shorter. He used 40-round custom-made BAR magazines as well.

It’s likely the name scattergun could also apply to the gun’s accuracy. With the barrel cut off, the front sight went with it. On top of that, the gun likely lost its crown and was just a bullet hose spraying .30-06 at a rather rapid rate.
Baby Face Nelson — Lebman M1911
Hyman Lebman was a leather worker and gunsmith. Some of his clients included some not-so-savory individuals, which include Dillinger and Baby Face Nelson. One of his products was a conversion to an M1911. He made them into machine pistols and added an extended magazine, a compensator, and a Thompson’s forward grip.

Baby Face Nelson was the most famous user of such a pistol. He was apparently friends with Lebman and even shared a Thanksgiving with him. He used one of these baby machine guns to kill Federal Agent W. Carter Baum and wound two others during the shootout at Little Bohemia.
Dillinger — Colt 1903
John Dillinger used a great many guns during his brazen bank robberies. The Thompson likely was his most famous, and he also owned a Lebman baby machine gun. The pistol he died with was the Colt M1903 in .380 ACP, sometimes known as an M1908. This little gun sat in his pocket the night he was killed.

He never got a chance to draw the weapon as he was shot from behind by Federal Agents. It’s not that big of a stretch to say he would’ve pulled if he could have. The man certainly wasn’t afraid to engage police officers.
Guns and Swords
Gangsters rarely grow old, and those who often disobey the law and endanger others tend to meet an early end. Still, our fascination with these gangsters and the tools of their trade will never fully disappear. Did I miss any gangsters, bootleggers, or bank robbers who deserve to be on the list? If so, let us know below!