Posts Tagged 'Crime'

The Great Escape (12-11-1921)

Tommy O’Connor was a young punk who specialized in armed robbery in the area around Maxwell Street.  In the spring of 1921 he killed a policeman who was trying to arrest him.  O’Connor was later caught, found guilty of murder, and sentenced to hang on December 15.

O’Connor was housed in the fourth-floor cell block of the old County Jail, just north of the Loop.  Things were quiet there on Sunday, December 11.  At 9:30 that morning the cells were open, and prisoners were taking their exercise in the common area of the cell block.  A single guard was on duty.

Suddenly, O’Connor produced a gun.  He took the guard’s keys, bound and gagged the man, and locked him in a cell.  Then O’Connor opened the gate to the cell block.  With four companions, he walked out.

“Chicago Tribune” diagram of O’Connor’s escape

On the third floor, O’Connor’s group subdued three more guards.  Next they took a freight elevator to the basement, where they overpowered a fifth guard, as well as five trusties.  The escapees then ran across the open-air yard, climbed over a shed, and dropped down into the alley behind the jail.

By this time, the alarm had been sounded.  Two guards rushed out of the building just in time to see O’Connor jump on the running board of a passing car, and force the driver at gunpoint to get-the-hell-away.

Two of O’Connor’s companions were immediately recaptured.  The other two were caught later.  Tommy O’Connor was never seen again.

Rumors persisted that O’Connor’s escape had been an inside job, but nothing was ever proven.  In later years, O’Connor-sightings were reported in various places around town.  The Legend of Terrible Tommy grew.  One story said he had gone to Ireland to fight for the IRA.  Another claimed he had repented his wicked ways and become a Trappist monk.


Now for a footnote on the nature of bureaucratic mind.  Tommy O’Connor had been sentenced to be “hanged by the neck until dead.”  A few years later, when the state abandoned hanging in favor of the electric chair, some nitwit decided that the gallows had to be saved, in case O’Connor were ever recaptured.

So the gallows was taken apart and stored.  When the new County Jail opened, it was moved there.  In 1977, officials concluded they weren’t likely to see O’Connor any time soon, and the macabre keepsake was finally sold.


Martyred Mayor (10-28-1893)

The grand Columbian Exposition was drawing to a close.  The eyes of the world had been on Chicago, and the city was feeling proud.  Then came the terrible news—Mayor Harrison had been killed by an assassin.

Carter Henry Harrison belonged to a distinguished family that gave the country two presidents.  In 1855 he arrived at Chicago as a young lawyer.  He was active in the Democratic Party and served two terms in Congress.  In 1879 he was elected mayor of the city.

Mayor Carter Harrison

Harrison was a popular, accessible mayor.  He often rode through the city streets on a white horse, greeting his constituents.  After serving four two-year terms, he retired.  But when Chicago was chosen as the site for the Columbian world’s fair, he ran for mayor once again, and was elected to a fifth term in 1893.

On this evening, Harrison had returned to his Ashland Boulevard home after a long day at the fair, and was napping in a back bedroom.  Around 8 p.m. a man named Eugene Prendergast appeared at the front door, asking to see the mayor.  The maid thought she recognized Prendergast and let him in.

A few moments afterward, the servants heard loud voices, then three shots.  They rushed toward the sound and discovered Harrison lying wounded on the floor.  Prendergast was gone.

The mayor died within twenty minutes.  A short time later, Prendergast turned himself in to the police.  He admitted the crime.  His motive?  Harrison had refused to appoint Prendergast as the city’s Corporation Counsel.

Chicago was plunged into grief.  The closing ceremonies at the Columbian Exposition were converted into a memorial for the fallen mayor. Prendergast was quickly brought to trial, convicted of murder, and sentenced to death.

The crowd outside the mayor’s home after the shooting

Prendergast’s brother appealed the sentence, saying that Eugene was insane.   The attorney for the appeal was not-yet-famous Clarence Darrow.  It was Darrow’s first murder case—and the only case he ever lost to the executioner.  The appeal was denied, and Eugene Prendergast was hanged.

Four years after Harrison’s murder, his son—also named Carter Harrison—became mayor of Chicago.  Like his father, the younger Harrison would be elected to the office five times.


The Fugitive in Custody (4-2-1934)

The fugitive from Chicago had been the object of a manhunt across three continents.  Today the chase ended in Turkey.

The fugitive was 74 years old.  His name was Samuel Insull.  And he was no ordinary fugitive.

Insull was born poor in London.  As a young man he caught the eye of Thomas Edison, becoming the great inventor’s private secretary.  Electricity was the new technology of the 1890s, and Insull got in on the ground floor.  It was like being the right-hand man of Bill Gates a century later.

1926–Insull the Hero

Insull helped build America’s electrical industry.  His talent was financial, not scientific.  After revamping the General Electric Company, he settled in Chicago.  Insull merged, modernized, expanded.  By the 1920s his holdings included Commonwealth Edison, Peoples Gas, the Chicago Rapid Transit Company, and several interurban railroads.

He knew how to make money, and the public bought into his companies.  Insull was also a philanthropist.  He built the Civic Opera House and footed much of the opera company’s bill.

In 1929 the Stock Market crashed.  As the country moved into the Depression, Insull’s companies suffered tremendous losses.  Thousands of investors lost their life savings.  Insull, the hero of the 1920s, was now the villain of the 1930s.

Insull was in London in October 1932.  Back in Chicago, a county grand jury indicted him for fraud and embezzlement.  That was followed by federal charges a few months later.  Before he could be extradited, Insull skipped out of England.

He dodged authorities for over a year.  Then, in the spring of 1934, he was arrested in Turkey.  He had been on a ship headed for Egypt.  On April 2, the Turkish cabinet decided to let the U.S. have him.

Insull was brought back to Chicago to face the music.  He claimed to have done nothing wrong.  He said he was being made a scapegoat by ambitious politicians.

1934–Insull the Scapegoat

He did have a point.  Insull was tried three separate times, in three different courts.  He was acquitted all three times.

After the last trial, Insull left the U.S. for good.  He died penniless in a Paris subway station in 1938.  But he has been immortalized, in an offbeat way.

Monopoly, the board game, was introduced when the Insull trials were front page news.  The next time you play, take a look at the cartoon Monopoly Man.  He’s the image of Samuel Insull.


Dingbat’s Funeral (3-11-1930)

In Washington today, the big story was the funeral of William Howard Taft, 27th President of the United States.  In Chicago, the big story was also a funeral.  The city was saying good-bye to the Dingbat.

The Dingbat was John Oberta, his nickname derived from a comic strip.  He was 27 at the time of his death.  Like Taft he was a Republican politician, the 13th Ward Committeeman.  Unlike Taft, he was a gangster.

Mr. & Mrs. Dingbat

Oberta was a protege of Big Tim Murphy, bootlegger and labor racketeer in the Back-of-the-Yards neighborhood.  One morning Big Tim opened his front door and had his head blown off by a shotgun blast.  A few months later, Dingbat married Big Tim’s widow.

Now Dingbat was gone, too.  He had been found shot dead in his car, along with his chauffeur, on a deserted road near Willow Springs.

By 1930 the garish gangster funeral had become a familiar Chicago custom.  Dingbat’s friends would not scrimp.  “I’m giving him the same I gave Tim,” Mrs. Murphy Oberta told reporters.

Dingbat was waked in his home on South Richmond Avenue.  He lay in a $15,000 mahogany coffin with silver handles, under a blanket of orchids.  Joe Saltis, Bugs Moran, Spike O’Donnell, and all of Dingbat’s pals were present.  So were assorted politicians.

Two priests of the Polish National Catholic Church conducted a brief service.  Then the pall bearers prepared to carry the coffin to the waiting hearse.  Out on the street, a crowd of 20,000 people had gathered.  (In Washington, half as many were reported at Taft’s funeral.)

The scene on Richmond Avenue

“Carry my Johnny out the back way,” Dingbat’s mother wailed.  “Don’t let them see him!  They didn’t care about him!”  The pall bearers ignored her and brought Dingbat out the front door.

The coffin was loaded, then the hearse moved away.  Following it were four carloads of flowers and a procession two miles long.  When the funeral cortege arrived at Holy Sepulcher Cemetery, hundreds more curiosity seekers were there to greet it.

Dingbat was laid to rest a few feet from Big Tim Murphy.  There was just enough space between them for another grave.  Presumably that spot was reserved for their mutual wife.

The murder of Dingbat Oberta was never officially solved.  And with the Great Depression fast descending on the country, the gaudy gangland funeral went out of fashion.


A Different St. Valentine’s Day Story (2-14-1936)

If you’re from Chicago, you probably know about the Saint Valentine’s Day Massacre.  On February 14, 1929, seven men were gunned down in the SMC Cartage garage at 2122 North Clark Street.  Most of the dead men were members of the Bugs Moran bootlegging gang.  The killings were likely ordered by rival ganglord Al Capone.


After 90 years, there’s not much new to be said about the massacre itself.  So I’m going to be talking about a neglected postscript.

The original “Scarface” was one of the movie hits of 1932.  As the name suggests, it’s a thinly-disguised biography of Capone.  Paul Muni is the star.

About halfway through the story, Muni decides to eliminate rival mobster Boris Karloff.  Karloff learns about the plot and disappears.  But he can’t stay put.  One night he goes bowling.

Meanwhile, Scarface Muni is at the opera when word comes that Karloff has been spotted.  So Muni and a few henchmen head for the bowling alley.  And they don’t take their bowling equipment with them.

Out on the lanes, Karloff is happily spilling pins.  “Now watch this one,” he tells the guy next to him.  He grabs his ball and trots to the line.

Boris Karloff goes bowling

Just as Karloff lets go of the ball, gunshots ring out, and he crumples to the floor.  But the camera follows the ball down the lane.  The ball hits the pins and they scatter–all except the 10-pin, which spins crazily in circles a few times before finally falling over.

Film critics loved the bowling scene.  They praised director Howard Hawks and his use of a slowly toppling pin as a symbol of Karloff dying off-screen.  In fact, the whole idea of killing a character in a bowling alley was brilliantly original.  That had never been done.

Gangland applauded the film, too.  Members of the Capone mob were tickled to see their exploits portrayed on the giant screen in glorious black-and-white.  Among those members was Machine Gun Jack McGurn.  McGurn is often credited as the planner of the St. Valentine’s Day Massacre.  Some writers claim he was the lead gunman.

McGurn was a sportsman.  He was a scratch golfer and an expert bowler.  Disdaining the wicked city where he made his livelihood, he owned a bungalow in sedate, suburban Oak Park.

Machine Gun Jack in court

On Saint Valentine’s Evening 1936, McGurn decided to go bowling.  Along with two friends, he drove into the city.  They arrived at Avenue Recreation, 805 North Milwaukee Avenue, about midnight.

McGurn and his pals removed their outer clothing and prepared to bowl.  Suddenly, three armed men rushed in, announcing a stickup.  During the confusion one of the intruders ran up to McGurn and pumped three slugs into him.

Machine Gun Jack died on alley two with a house ball in his hands.  One homey touch was the unsigned Valentine left on his body:

You’ve lost your job,

You’ve lost your dough,

Your car and your fine houses.

But things could be worse, you know–

You haven’t lost your trousers.

Machine Gun Jack goes bowling

The murder was never solved.  What’s unmistakable is the eerie echo of Karloff’s death in “Scarface.”  Someone had seen the movie, been impressed by the staging, and decided to copy it.  Once again, life imitates art.

Happy Saint Valentine’s Day.



The Story of a News Photo

During the 1920s, a daily newspaper would go to outlandish lengths to top its rivals. If you were the first one with the big story, you sold more papers.  Ditto if you had an exclusive story—a “scoop.”  Ditto again if you had an exclusive photo.

Tom Howard being fitted with his ankle camera

Tom Howard being fitted with his camera

Tom Howard was part of this milieu. In 1928 the young Chicago Tribune photographer took one of the most famous photos in newspaper history.  And it all began with a scruffy little murder in Queens, New York.

Ruth Snyder was an unhappily-married housewife in her early thirties who was having an affair with a corset salesman named Henry Judd Gray. On March 19, 1927 they killed Ruth’s husband Albert for the insurance money.  They tried to make it look like part of a robbery gone wrong.

But the lovers proved to be inept criminals. The police quickly demolished their story, and they wound up accusing each other of dreaming up the scheme.  Ruth and Henry were tried for first-degree murder.  Both of them were found guilty, and sentenced to die in the electric chair at the state prison in Sing Sing.

The New York Daily News was a tabloid that had built its reputation on sensational news photos.  Ruth Snyder was going to be the first woman executed in several years, and publisher Joseph Medill Patterson wanted a picture of the execution.  Trouble was, photographing an execution was not allowed, and prison authorities knew all of the Daily News photographers.  So Patterson phoned his cousin, Chicago Tribune publisher Robert R. McCormick.

McCormick agreed to lend Tom Howard to the Daily News. In New York, Howard obtained press credentials to attend the executions as a writer.  On January 12, 1928 he arrived at the prison with a miniature single-shot camera strapped to his ankle.  A wire attached to the shutter ran up his trouser leg to a trigger-release concealed in his coat.

Howard waited while Henry Judd Gray was executed. Then came Ruth Snyder’s turn.  Howard edged forward.  As the current surged through her body, Howard squeezed the trigger release.  Then it was over, and he rushed back to the Daily News offices in Manhattan.

The famous photo

The famous photo

Howard had no way of knowing if the plan had worked, until the photographic plate was actually developed. But it had worked.  Four hours after Ruth Snyder’s execution, Daily News extras were on the street, the entire front page filled with Howard’s photo of her death throes.  The headline simply read “DEAD!”

Prison officials were outraged by the picture. They talked about bringing charges against Howard and the Daily News.  But since no laws had actually been broken, the matter was dropped.  Still, in the decades since, anyone admitted to an execution site undergoes a thorough search for concealed cameras.

Tom Howard returned to his career in Chicago. When he died in 1961, he was the chief photographer at the Sun-Times.


Best Wishes from Leo (12-29-1923)

Today some 160 Chicagoans received New Year’s greetings from Leo Koretz.  The cards were inscribed with verse:  “If I could be transported/ This moment to your door/ I’d bring you smiles by dozens/ And good wishes by the score/ —Leo Koretz”

Leo Koretz

Those 160 people certainly knew Leo Koretz.  He’d convinced them to invest $10 million to develop oil land in Panama, then disappeared with the money.  His plan turned out to be a giant con.

So where was Leo now?  The cards had been mailed in Chicago.  As it turned out, he was in Nova Scotia, living it up with assorted women.

Koretz was extradited, convicted of his swindle, and sentenced to state prison.  He told reporters he’d never serve his time.

Before he could be transferred from the county lockup, one of his lady friends brought him a five-pound box of chocolate.  Koretz ate it in one sitting and keeled over dead, as he’d planned.  He was a diabetic.