Vintage Gangsters

Public Enemy Number One

Actually, I sometimes have the same title when I’m with my conservative family.

The esteemed title actually belonged to notorious gangster John Dillinger.



Dillinger was the quintessential 1930s gangster with a drama-filled life and a death to match. History has made Dillinger a combination of a cult figure and a folk hero. During his bank robberies, Dillinger would also destroy bank mortgage and loan records, freeing people from their debts.

We need a millennial Dillinger to do the same for student loans.

If you’ve been keeping up with my weirdness, I’m deep into this 1920s and 1930s gangster shit and there’s no turning back. It doesn’t help that I’ve been watching Boardwalk Empire.


Nucky Thompson approves this message.


Dillinger’s crime spree from September 1933 to July 1934 made him a
household name feared by many.

During the height of the Great Depression, Dillinger and his gang killed 10 men, wounded 7, robbed countless banks and police arsenals, and staged 3 escapes from prison.
Dillinger was born in 1903 in Indianapolis to an upper-middle-class family. Dillinger’s
father owned a grocery store and the family was well-respected in the community.
His mother died when he was age 3. Dillinger had a normal childhood and did not exhibit any indication of future criminal behavior until his early teens. Dillinger’s questionable behavior began to appear after his father remarried. He had a strained relationship with his stepmother and resented her. Perhaps if things had gone differently, our favorite 1930s gangster might have been in a Disney movie.

Very little information is known about the exact details of Dillinger’s
childhood. Some accounts claim he was “unremarkable” and well-behaved. Others claim he was a petty thief and was a member of a youth gang called “The Dirty Dozen”. I’m going to go with option 2.

Dillinger was extremely charming and charismatic, characteristics that were apparent
during his crime spree. Dillinger’s family moved to a rural town outside of Indianapolis
and joined the Quaker Church. Dillinger did not adjust well to rural life and acted out frequently leading to the beginning of his crime spree. I would also act out if I was forced to move to the middle of nowhere in Mike Pence country and join a church.

Dillinger’s first major criminal offense was stealing a car in reaction to being denied to propose to a local girl he had fallen in love with Dillinger was caught by the police being his first escape attempt. Dillinger joined the Navy to legally escape jail only to be AWOL after a few months and subsequently being dishonorably discharged.

Soon after Dillinger married Beryl Ethel Hovious in 1924. Hovious was from Mooresville, Indiana where his family lived. SPOILER: married life did not calm his behavior.
To escape the responsibilities of marriage and adulthood, Dillinger began frequenting local bars and pool halls. This introduced him to the world of crime which he would later be very well acquainted with.
Facing financial difficulty, Dillinger and a man named Edward Singleton robbed a
grocery store which turned into a complete disaster. Dillinger mistakenly questioned locals about the hours of the store and about money that might be inside. During the robbery, he accidentally set off a gun and struck the owner of the store in the head with a lead pipe.

Dillinger’s mistakes made it too simple for the police to catch him. He was arrested and
was sentenced to 10-20 years in the Indiana State Reformatory where he was incarcerated from 1924 to 1933.

Dillinger was not a model prisoner and spent most of his time in solitary confinement. It is believed that Dillinger was embarrassed by his first robbery and hardened by prison life wanted to become a more efficient criminal once released. In prison, he told a fellow inmate,”I will be the meanest bastard you ever saw when I get out of here.”

It’s good to have goals.
Dillinger met like-minded men in prison, discussed notes on crime, and planned his future robberies.  Dillinger was denied parole in Indiana and was transferred to a tougher prison in Michigan. He improved his behavior and planned for another parole hearing in 1933. Dillinger won and was released from prison after only serving an 8-year sentence.

After his release from prison, he had trouble finding work as 1933 was the height of the Great Depression. In September of the same year, Dillinger went to prison again for robbing 2 banks in Ohio.

Dillinger made his final escape from prison and stole a police car, leading to the nationwide search for Dillinger lead by the FBI.

He was caught in Tuscon, Arizona and escorted back to Indiana and then to Chicago where he had robbed a bank only then days before being captured in Arizona. Dillinger made another escape from the jail in Crown Point, Indiana where he was held in a cell with extra guards.

According to the FBI, Dillinger escaped from the Crown Point Jail with a fake pistol carved out of a potato. However, deputies in Crown Point reported the gun was real. I’d like to think it was a potato, so let’s go with that.

He escaped to Minneapolis with his girlfriend, Evelyn “Billie” Frechette. After FBI agents were staking out their apartment, the couple went back to Mooresville, Indiana to Dillinger’s family.

They then went to Chicago where Billie was arrested by the FBI in a bar. She was charged with harboring a criminal after she refused to disclose Dillinger’s location and served 2 years in prison from 1934 to 1936. After her arrest, she and Dillinger never saw one another again.


Vintage lady criminals are the best criminals.



Dillinger stayed in Chicago until his death. The FBI didn’t know where he was because Billie did the ol’ Tammy Wynette “Stand By Your Man” and refused to talk.

When a cop car he had stolen was found dumped on a street in Chicago, the FBI focused on tracking down their most wanted in the Windy City.

In Chicago, the wanted man found it was easy to hide in the crowded city. Dillinger even worked as a store clerk under an alias and attended several Cubs games at Wrigley Field. Fun fact: the cops looking for him also regularly attended Cubs games.


I’m sensing a theme.


While hiding out in Chicago, Dillinger had an associate find a doctor willing to perform some minor plastic surgery procedures on him. Dr. Wilhelm Loeser, a friend of a friend agreed to perform the procedures.

Loeser had been arrested for narcotics violations and spent several years in prison. He also admitted that he had performed facial surgery on himself and altered his own fingerprints with lye.

Supposedly, Dillinger had several moles removed on his forehead, made an incision in his nose and an incision in his chin and tied back both cheeks.

As the search ensued, a $10,000 reward was offered for any information. Anna Sage, a madam at a brothel in Gary, Indiana contacted the police saying she knew of Dillinger’s whereabouts. Dillinger’s new girlfriend, Polly Hamilton (sorry, Billie), had worked for Sage.

Sage, was a Romanian immigrant and threatened with deportation. She struck a deal with the FBI; she’d help them get Dillinger if they would help her with her citizenship. They agreed to her terms, but the deal fell through and Sage was deported in 1936.

Sage, Dillinger and one of Sage’s girlfriends were going to the movies the following night. The police and FBI stood outside the theatre waiting for Dillinger. On July 22, 1934, Dillinger was shot by FBI agents outside the Biograph Theatre in Chicago and was pronounced dead the same night.

The freakin’ FBI waiting outside a movie theatre to kill you is hardcore. Dillinger’s body was on display at the Cook County Morgue where an estimated 15,000 people went and viewed his body, because what else would you do during the middle of the Great Depression? I’m guessing a John Dillinger dead body viewing would get a 10/10.

Random Vintage Gangsters

 Let’s Celebrate Valentine’s Day With A Massacre 

February 14 is a day of many emotions and not just love. Valentine’s Day is a point of contention for many. In reality, it’s just another day that really doesn’t mean much of anything. Unless you just so happened to be a victim of the infamous Valentine’s Massacre in 1929. 


If you are offended by vintage crime scene photos, leave this blog now.


Chicago, 1929. Prohibition was in full swing and the mafia ruled. Honestly, the 1920s looked super fun. Would Rsvp “yes” to a 1920s party. At 10:30 a.m. on Valentine’s Day 1929, seven men were murdered in a shootout at a warehouse on Clark Street in Chicago. Five of the men killed were members of the Chicago North Side Gang led by Bugs Moran. The murders were planned by none other than Al Capone, which is something you probably already knew. Side note: 10:30 in the morning seems early for a planned gun battle/massacre. Murdering a bunch of rival gang members seems more like a nighttime activity.


Al Capone


The initial plan was to lure Bugs Moran to the warehouse with a promise of a cut of illegal whiskey that had been shipped in from Detroit and kill him in order for Capone’s gang to gain more control over Chicago’s illegal liquor operations. Also, an associate of Moran’s had murdered members of Capone’s gang in 1924, Pasqualino “Patsy” Lolordo and Antonio “The Scourge” Lombardo. Side note 2: those are the best names EVER. These gangsters with their fighting and trendy names are total petty drama queens. 

Once members of the North Side Gang arrived at the warehouse, some of Capone’s men were there dressed as police. Moran, who was supposed to already be at the warehouse, was running late that day. When he saw police going into the warehouse, he waited outside. The police were actually Capone’s men and were inside murdering his men. 

Capone’s crew was successful in taking down so many of Moran’s men that Capone’s gang took complete control of the Chicago operations (or racket if you want to go full old-school gangster).


Bugs Moran looks like the type of guy who randomly talks to you in the grocery store and makes a bad pun about the weather. 


No one was ever brought to trial or charged with the murders. Both Capone and Moran blamed each other for the murders. Capone denied that he was personally involved that even claimed he was at his home in Florida the day of the murders.


Like most of the mafia crimes of yesteryear, this was one never officially solved. This was mainly because of police corruption and payoffs to public officials, which never happen today *wink, wink*.

Fun fact: Al Capone was actually arrested for tax evasion and went insane from syphilis.

On that note…