Vintage Mobster Photos From The Good Ol’ Days

Published

5 years ago

December 6, 2019

Money + Investing Staff

Mobsters and Mafia bosses are some of the most infamous people in pop culture history. Not only are they known for some of the shadiest business and criminal practices in western history, but their organized crime led to lavish lifestyles, but also devastating activity for those they left in their wake.

Known for their ruthless behavior, mafiosos and their confidants often relished in their indulgence a bit too long, and were caught red-handed. However, nothing tells a story better than pictures from those who were there, so here we present to you the most epic photos captured of the world’s most notorious gangsters.

A New Officer

He’s getting ready to face the mob on their turf. He’s not a famous officer. So who knows if he ever collared a mobster or if he ended up on the take.

South Side Handbook War

Racketeer Carroll “Kickey” Corcoran died tragically behind the steering wheel of his car because he happened to be mixed up in a shooting. It was infamously referred to as the South Side Handbook War because of the gaming operation Kickey found himself caught up in.

The Old Poisoning Trick

Officers are exhuming a body because the circumstances of his death are quite coincidental. Otille “Tillie” Kilmek would take life insurance out on her husbands and then poison them. Officers became suspicious after her first three husbands died that way and the fourth one became ill.

Lucky Beyond Belief

Three Fingered Jack seen here leaving a courtroom just got off another charge of murder of a police officer. He had been charged twice for killing officers. But, he obviously had more money than the prosecutors.

Infamous Dillinger

Leaving the courtroom on charges of robbing the First National Bank, John Dillinger is seen here with a motley looking crew. Throughout his career, Dillinger robbed 24 banks as well as 4 police stations.

Prison Riot

Have you ever wondered how prison guards are able to keep 1,500 prisoners in check? They do a great job. But sometimes, inmates tend to riot and they can make a real mess when they do.

The Good Ol’ Days

Blocking their faces from the photographer, mobsters are being arrested. They appear to be heading to transport. But with no officers in the photo, it’s hard to tell what’s really going on.

Here’s Bravery

They killed his brother. James Morelli is standing while Nick Kuesis points at him and points out that he’s one of the murderers. Yes, Nick’s brother is John Kuesis and it appears Nick has no care in the world for the message the three mobsters sent the first time.

Illegal Alcohol

To think that Al Capone could not get collared over his illegal alcohol operation. They had to get him on tax evasion. This is during the Prohibition when police had nothing better to do but to harass people and break their bottles of whiskey.

A Murder Of Mobsters

Tony Accardo was a primary suspect in the St. Valentine’s Day Massacre. Here two police investigators are inspecting a firearm to see if they can find some evidence.

Watcha Get For Snitching

Thomas Daley, James Morelli, and Lowell Fentress gunned down a man, and his name was John Kuesis. His sister, Estelle Cantoumanos, grieved over him at the scene as she identified the body. This is the ultimate consequence of what happens when a man snitches on the mob.

The Walk Of Al Capone

Al Capone is being led out of the courthouse by officers on his way to prison. Don’t you like how he’s not in handcuffs? They had more trust back then or something.

Thrill Killers

Richard Loeb and Nathan Leopold Jr. were known as the “Thrill Killers.” They look particularly sinister in this photo, which is thanks to the photographer with a knack for capturing the moment.

The Great Catch

Al Capone was able to evade the police and criminal processing his entire career. That is until they finally got him on tax evasion. The lawyer to his right looks like he’s going to be sick because he’s probably imagining how he’ll get whacked.

The Lawyer

If you’re wondering how many mobsters could get off their charges, here’s your answer. Clarence Darrow was the lawyer to many of them. Probably the reason he looks so exhausted in this photo.

Getting Booked

The infamous mugshot of one of the most famous mobsters. Al Capone was considered by many people to be a nice guy. That’s because he gave to the community, that is unless you crossed his path the wrong way.

Not Happy This Time

Al Capone is not enjoying this day. He’s walking into court and who knows why he’s not smiling. Could it be because he knows his fate or that he’s just not in the mood for photos that day?

These Mugshots

How in the world did the police have enough foresight to get this picture of Edward Dalton and De Gracy? This is a mugshot by the way. Sitting relaxed in their chairs with no handcuffs on or anything, it looks like they’re posing in a studio.

The Bulletproof Shield

Elliot Wisbrod stands behind his invention while an officer tests it. That’s called believing in your work. I’m pretty sure he tested it first before he stood behind it.

Out-Manning The Force

The police didn’t have guns like these. Only mobsters had access to them and law enforcement often found themselves outmanned.

A Fatal Drink

Her name was “Moonshine Mary” Wazeniak who was convicted of something very interesting. When a shot of her moonshine killed George L. Rheutan, she was convicted of selling fatal moonshine. Some people would say all moonshine is fatal, but have they died from it?

Real Gambling Thugs

With a big smile on his face, George McManus was charged with murder of another gambler. But, that’s why they get the good lawyers. George was acquitted of the charges and walked out of the courthouse happy.

Old Time Drug Dealer

William Moore was a very intimidating drug dealer. In fact, some of his product was completely fake and no one complained. They cared more about their life than they did about complaining over terrible service.

Not The Airport

“Machine Gun” Kelly seen here walking in handcuffs. He kidnapped Charles F. Urschel who was a big time oil guy. That plan didn’t go well, but these officers escorting him should be happy to be alive.

Bootlegger

Joseph “Polack Joe” Saltis seen here signing papers was a bootlegger who dominated the Southwest Side of Chicago. He’s at the police station, but he was good at dodging charges and amassed great fortune in his lifetime.

A Real Thug

This man does not look like a nice guy. That’s because Walter Smith is a cold blooded murderer. He seriously didn’t care if he shot them in public, in the middle of the day.

Dillinger Escape Plan

John Dillinger is seen here handcuffed to Deputy Sheriff Pierce so he couldn’t run. Dillinger was facing murder charges as he sat in the courtroom. He ended up getting sentenced to prison, but later escaped as he was known to do.

Girl Bandits

These girls evaded police for years. Here they are being questioned by cops and I’m sure the conversation was quite lively. They were finally caught in 1927 on a home robbery.

Original C.S.I.

These are the guys who started it all. But, they were at a major disadvantage. Still, using the primitive tools they had available at the time, they were able to get their man some of the time in a steadily advancing field that can solve anything with anything now.

Central Booking

The lineups back in those days were always interesting, because they almost looked like photoshoots considering all of the convicted felons would be wearing identical suits. Hard to imagine fancy garb on a criminal like this today.

Slinged Up

This quad of gangsters were all apprehended together, with one likely taking some damage while trying to flee from authorities in what almost always were contentious confrontations in the streets. This was a bust of some repeat criminals by what would become future Police Chief Bill Mackay.

Funeral Proceedings

Funerals for mobsters were basically a thing of spectacle, as many “fans” and supporting members of each faction would surround the memorial services in big numbers. Unfortunately, with mob-style activities, death was a regular occurrence that people became numb to.

Capone At Home

Al Capone was by far the most widely known and celebrated of the mobsters, and much of his private life became emulated by wanna-be gangsters. Here he’s seen relaxing and enjoying as cigar as he waits out the results of his trial in his Miami home.

Hiding From Cameras

Whilst attending the trial of Al Capone, his fellow cronies and presumably some of his henchmen look on, but hide their face from the nosey press. Just like funerals, court hearings and trials became a thing covered by big media, and affiliates tried to conceal their identities.

Strutting Out

Leaving the courthouse meant lots of additional security, not only from the gawking press and onlookers, but obviously from rivals who might be looking to get a viral hit to grab extra attention. However, the dismissal didn’t mean an absence of the always present cigar.

Sidney Kelly

Kelly’s main crime was running a gambling house, and that meant a lot of other nefarious activity was often taking place within the confines of the residence. He was arrested many times over the years before being caught in the crossfire at the age of 48.

Pat Riley

Patrick Riley was affiliated with some of the most notorious names in the mob at the time, including John Dillinger, Baby Face Nelson, and many of that crew. Regardless of who he knew, he couldn’t stay out of trouble, and ended up in the slammer as shown here.

Skukerman

Sydney Skukerman was the one responsible for safeguarding a warehouse, which was serving as a makeshift distribution center for the smuggling and trafficking of illegal goods, including but not limited to alcohol, firearms, and of course illegal narcotics.

Wives’ Loyalty

The wives of many mobsters were loyal to their husbands down to the end, and even threw large public fits outside the courthouse while screaming proclamations of their partner’s innocence. This was often labeled fanaticism, and brushed off as misguided idolatry.

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