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Sunday, February 25, 2024

The Man Who Shot Dillinger

 


Chales Winstead


The Great Depression was a time of grinding poverty, shanty towns, soup lines, and trains laden with tattered hoboes looking for work.  Thousands lost their homes and farms to foreclosure.  As a result, many blamed the banks for their misfortunes.  Gangsters, such as “Baby Face” Nelson, “Pretty Boy” Floyd, Bonnie and Clyde, Alvin Karpis, and John Dillinger caught the public’s imagination.  Because they robbed the hated banks, they were often seen as heroes and modern day Robin Hoods.  Nevertheless, they shot people, especially police officers and bank employees with families to support.  The money they robbed didn’t go toward charities for the poor, but toward their own pockets. 

 

Back then, bank robberies were committed with an impunity that would dumbfound today’s  innocent, law-abiding public.  During the twenties, law enforcement in major cities, such as Chicago, were hampered by corruption, stingy budgets, and state and local jurisdictions that wouldn’t cooperate with each other.   To make matters worse, the bank robbers were heavily armed with submachine guns, automatic rifles, and shotguns, awesome military grade firepower the police could barely counter.  By the time police officers and sheriff deputies gave chase, the criminals were in another state jurisdiction, holed-up in back-alley apartments and remote farm houses, except for Bonnie and Clyde; who mostly just lived in their car.  Their stolen money could buy a whole lot of underworld support, especially informants who could warn them if the law was getting too close.  If you had the money and corrupt officials that looked the other way - crime paid!

 

That all changed during the early thirties with the emergence of the federal government’s crime fighting unit - the Federal Bureau of Investigation or FBI.  Under the leadership of a former government attorney, J. Edgar Hoover, the FBI would become the nation’s premier law enforcement agency.  A self-disciplined, neatness freak, who lived with his mother, Hoover surrounded himself with suited, well-groomed, extremely loyal agents, mostly dapper Southern boys with law degrees.  However, they were also unarmed investigators with little, if any, police experience.  Hoover himself had never arrested anyone.  Snappy appearances were great for newspaper photos, but not so great for armed manhunts that could get you killed during a gunfight.  What the FBI needed to compensate for its youthful inexperience, especially against heavily armed, hardened gangsters, was a tough, frontier approach to law enforcement.  What better place to look than Texas.

 

Referred to as the “Cowboys,” these grizzled FBI agents from the Southwest weren’t anything like Hoover’s “young and grateful” type.  They wore cowboy hats, chewed and spit tobacco, drank, and packed oversize revolvers.  But more important, they could look you straight in the eye, and without hesitation, shoot you dead.  Charles Winstead, who often carried a .357 Magnum revolver, fit that type “to a T.”

 

Charles “Charlie” Winstead was born in Sherman, Texas on May 25th, 1891.  Unlike the buff, silent character portrayed by the actor Stephen Lang, in the movie “Public Enemies,” he was 5 feet, seven inches tall and weighed only 135 pounds.  Winstead was anything but silent, if riled, he wouldn’t hold back, vocally or physically; a trait that would eventually cost him.  In one incident, he struck a deliveryman who called him an “sob” over a parking space.  Before joining the FBI, Winstead served in the army during World War I and was a deputy sheriff in a number of Texas counties.  After joining the FBI, he was sent to the Dallas field office where he participated in unsuccessful hunts for Bonnie and Clyde and “Machine Gun” Kelly.  Though lacking in education, Winstead had a keen insight into the criminal mind and could conduct an investigation.  His big break came with his arrest of 1920’s bank robber Harvey Bailey in Rhome, Oklahoma.  Bailey was referred to as the “Dean of Bank Robbers.” So successful at his profession, he opened a chain of car washes and gas stations throughout South Chicago, eventually losing it all in the 1929 stock market crash.   In May, 1934, Winstead boarded an airplane at Dallas’ Love Field for a trip to Chicago; he was being transferred to help hunt down the most notorious bank robber in U. S. History - John Dillinger.

 

John Herbert Dillinger could probably never remember a time when he wasn’t in trouble.  Born on June 22, 1903 in Indianapolis, Indiana, he was a bully at school and stole cars as a teenager.  To avoid a further downward slide, Dillinger enlisted in the U. S. Navy but eventually deserted while his ship, the USS Utah, was docked in Boston Harbor.  He was later dishonorably discharged.  Out of a job, newly married,  and without an employable background, Dillinger turned to crime, robbing $50 from an elderly grocery store owner in Mooresville, Indiana.  He was arrested and received a 10 year sentence.  While incarcerated at Indiana State Prison, he learned the basics of bank robbery from fellow inmates, stating “I will become the meanest bastard you ever saw when I get out of here.”  He was as good as his word after being paroled on May 10, 1933.  What followed was a string of 24 bank robberies throughout the Midwest with a gang of ex-convicts he knew in prison. To obtain needed arms and bullet proof vests, he brazenly held-up police stations. 

 

Dillinger’s career came to a screeching halt when police in Tucson, Arizona arrested him while he was hiding out.  He was extradited to Crown Pointe, Indiana to stand trial for a bank robbery in East Chicago.  The jail house was reinforced with additional guards, turning it into an armed camp.  A swarm of news reporters descended on Dillinger’s jail cell.  He took full advantage of the publicity, presenting himself as a heartfelt, working class type who only robbed banks to make a living. “I was just an unfortunate boy who started wrong,” he told reporters.  In one news photo, he had his elbow resting on the shoulder of the county prosecutor, as if they were the best of friends.  Dillinger’s public stock rose further when he escaped.  Using a hand-carved wooden handgun, dyed with shoe polish, he made a clean getaway without a shot being fired.  Afterwards, the bank robberies continued.

 

It was all too much for the FBI to ignore and simply pass on to local law enforcement.  Under famed Special Agent Melvin Purvis, the Chicago FBI office ramped up the search for Dillinger; who suffered a leg wound while robbing a bank in Mason City, Iowa.  A break came when the owner’s wife of the Little Bohemia Lodge, near Manitowish Waters, Wisconsin, notified authorities of Dillinger’s presence.  Dillinger, recovering from his leg wound, hid out in an upstairs bedroom along with fellow gang members, including the violent, hot-tempered “Baby Face” Nelson.  Purvis and his agents quietly surrounded the lodge.  Their plan unraveled when the car of a lodge customer came down the driveway. The agents yelled at the driver to stop, but he couldn’t hear them because he had turned on the car’s radio.  The agents opened fire, killing the innocent driver and alerting the gangsters inside the lodge.  Machine gun fire erupted from the lodge’s upstairs windows, holding off Purvis’ men long enough for Dillinger and his gang to escape out back, scattering into the nearby woods.  “Baby Face Nelson” shot and killed an agent before stealing his car and getting away.  Overly sensitive toward public criticism and the political repercussions that followed, Hoover pulled out all the stops to get Dillinger - dead or alive.  

 

After Winstead landed, he was driven to the Chicago office to meet Purvis and fellow members of the newly created “Dillinger Squad.”  It became obvious to squad members; they were not  here to capture Dillinger, but kill him.  Agents fanned out across the Midwest to question Dillinger’s family and close associates with no results.  A multitude of potential informants telephoned, but usually proved unreliable.  After months of searching, a reliable informant was finally found, a former madam from the Chicago underworld. 

 

Known in crime lore as “The Lady in Red,”Ana Sage was a Rumanian immigrant who had a talent for managing whorehouses.  Starting out as a “five and dime” prostitute at the Harbor Bay Inn in East Chicago, she eventually ran the place after the owner was sent to jail for selling hard liquor.  Sage was so successful that the Harbor Bay Inn became a well-oiled, established den of inequity at the going rate of $2 a tumble. In 1923, she rented an entire hotel for her operation, the forty-six room Koster Hotel, later referred to as “The Bucket of Blood” for all the knife and gunfights that occurred inside.  East Chicago’s corrupt police force kept her out of jail until her luck finally ran out.  Indiana’s reform-minded governor referred her to the federal immigration authorities for deportation.  With no whorehouses to run, Sage resided in a number of Chicago apartments she also used for call girl operations.  Among her girls was Polly Hamilton, a pretty sandwich shop waitress.  Introducing himself as “Jimmy Lawrence,” a clerk at the Chicago Board of Trade, Dillinger began dating her.  Facing deportation and knowing the real identity of Polly’s boyfriend, she decided to inform on Dillinger in exchange for not being deported. The FBI agreed to the exchange after Sage told them her, Hamilton and Dillinger would attend a movie theater on July 22, 1934.   She would be wearing an orange skirt to signal their arrival.  FBI agents surrounded the Biograph Theater along with members of the Chicago Police Department.   Purvis would light a cigar to signal Dillinger’s exit from the theater.  Shortly after the movie ended, Dillinger came out of the theater; Purvis lit his cigar.  Dillinger noticed their approach and tried to escape down an alley.  Winstead and two other agents opened fire with their handguns.  The steady-handed Texan fired the fatal shots that killed Dillinger.  One struck him in the back of the neck and exited just below his right eye.  Curiosity seekers surrounded the body.  Using their newspapers and handkerchiefs, they sopped up the blood as souvenirs.

 

Winstead received a letter of commendation from Hoover.  After helping track down “Baby Face” Nelson, he returned west, serving in FBI offices at El Paso and Albuquerque. Winstead had little use for Hoover’s imperious demeanor, telling one rookie, “Everyone at headquarters knows Hoover is an egomaniac, and they all flatter him constantly.  If you don’t, you’ll be noticed.”  It was a female news reporter that ended Winstead’s FBI career. Resentful of her questions, he insulted her and accused her of being a Communist after she downplayed America’s war effort during World War II.  Always sensitive toward the press, Hoover demanded an apology from Winstead. Instead, Winstead did what any prideful Texan with a disdain for federal popinjays would do.  He told him to, “Go to hell !”  Afterwards, he resigned from the FBI on December 10, 1942, four years short of receiving tenure for government retirement.  Winstead served as a captain in Army Intelligence during the war.  He was also briefly in charge of security during the secret A-bomb testing at Los Alamos, the “Manhattan Project.”  Before retiring and taking up horse ranching, he was employed as a sheriff’s deputy and private investigator in New Mexico.  Charles B. Winstead died of cancer on August 3, 1973 and was cremated at Albuquerque’s Fairview Park Crematory.          

 



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