Texas, USA
A Bulletproof Life
On the big screen, Uncle Charlie gets credit for gunning down Dillinger

John Dillinger, notorious criminal, shortly before he was killed. He posed with a pistol in one hand and a sub-machine gun in the other.
IMAGE: BETTMANN/CORBIS

Uncle Charlie always wanted to be a cowboy. He knew cattle. He knew horses. And he was very good with guns. Good enough so that in 1934 on the streets of Chicago he faced the most notorious American outlaw of the 20th century and beat him to the draw.

The 2009 film “Public Enemies” is the latest in a long line of movie bios of John Dillinger and the gangsters of the ’30s. Most of these movies have taken an already colorful history and outrageously embellished it to heighten drama, sentiment, violence or whatever it took to create a box-office success. “Public Enemies,” directed by Michael Mann and starring Johnny Depp as Dillinger, is no different in that respect.

However, in one respect, it is different from all those other Dillinger biopics. This is the first one that actually names Charles Winstead—who everybody in my family always called Uncle Charlie—as the man who, according to some accounts, shot Dillinger.

Born in 1891 in Sherman, my great-uncle Charles Winstead, played by Stephen Lang in “Public Enemies,” was just a little late to be a part of the classic Wild West era. But he made up for that by seeking out places and occupations that hadn’t yet yielded to civilized behavior.

After working in the cattle business in North Texas as a young man, he moved down to the Valley and entered law enforcement as a deputy sheriff in Brownsville.  Uncle Charlie’s reminiscences of those days are mostly about various gunfights in which he and his fellow lawmen participated.  

Uncle Charlie enlisted in the Army during World War I and returned to law enforcement after the war. In 1926, he became an agent of the fledgling Bureau of Investigation (now known as the Federal Bureau of Investigation, or FBI).

The early Depression era saw the rise of gangsters and desperados with descriptive names like “Pretty Boy” Floyd, “Baby Face” Nelson and “Machine Gun” Kelly. Uncle Charlie got to know them well because he chased them all over the map.

Uncle Charlie spent a whole lot of time chasing Bonnie Parker and Clyde Barrow in the East Texas oil patch. He almost caught up with them a couple of times; once in Gilmer he believed he’d found one of their recently stolen cars still warm, but they escaped. As he used to put it: “I wasn’t the only one that didn’t find them.”

In spring 1934, Uncle Charlie was told to get on a plane and report to the FBI’s Chicago field office. Dillinger and his gang were robbing banks, breaking people out of prison and embarrassing law enforcement officials as they became renegade Robin Hoods for a broke and bank-hating America.

Uncle Charlie arrived in Chicago wearing a cowboy hat and a gabardine suit. The other agents nicknamed him “Cowboy.”

The FBI force in those days included lawyers and accountants. Very few agents were experts with firearms. The Texas agents, my great-uncle among them, were an exception. The Texas contingent became a latter-day SWAT team whenever a gun battle with outlaws was expected.

On July 22, 1934, outside the Biograph Theater in Chicago, one was expected.

A tip from the famous “Lady in Red” had Dillinger going to a movie with a couple of his lady friends that night. Uncle Charlie spotted him right away. The agents had been instructed to take Dillinger “alive if possible,” but Dillinger sensed their presence and went for his gun. According to an FBI account, three of five shots fired by three agents hit Dillinger; some reports credit Winstead with firing the fatal shot. As Uncle Charlie would say in later years, “I didn’t read him his rights.”

If you saw “Public Enemies,” you probably remember the scene where Uncle Charlie kneels down and listens to Dillinger’s last words—a heartfelt and sentimental message to his lady love.

I don’t want to disillusion you or spoil the movie, but while Uncle Charlie did lean over Dillinger to hear him mumble something, he apparently couldn’t understand what the dying gunman said.

If all this had happened in the modern era, Uncle Charlie would be on all the late-night TV talk shows and have a book deal. Things were different then. The FBI didn’t want to name specific agents. The only FBI men really in the public eye were agent Melvin Purvis and Director J. Edgar Hoover. Even though these two privately congratulated Uncle Charlie for being one of the men who brought Dillinger to justice, he never took much public credit until decades later.

During the time of so-called “public enemy” criminals, Uncle Charlie also was in on the capture of Alvin “Creepy” Karpis and was on the team that cornered the infamous Ma Barker gang and shot Ma and her son Freddie.

In the early days of World War II, Uncle Charlie, then stationed in Albuquerque, New Mexico, gave an interview to a newspaper reporter in which he talked about communism. (He didn’t like it.) He was ordered to apologize by Hoover for criticizing our Russian allies in time of war. Uncle Charlie told Hoover to “go to hell.”

That effectively ended his career with the FBI. Soon thereafter, the Army asked him to accept a commission and become chief of security for a new top-secret military project in Los Alamos, New Mexico. My great-uncle was one of the first Americans to learn about the atomic bomb. Then he spent the rest of the war suppressing all knowledge of it.

After the war, Charlie Winstead stayed in Albuquerque and acquired enough land to start his own ranch.

My mother still has the letter from Hoover congratulating Uncle Charlie for his “fearlessness and courageous action” in the Dillinger episode. He got interviewed a few times when some reporter would figure out that the gentlemen rancher had a colorful past, but he never bragged about his exploits. He usually quoted his favorite bromide: “Dillinger came out of the theater and died of lead poisoning.”

Charles Winstead died in 1973 at the ripe old age of 82, living the cowboy life he had always wanted.

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Marco Perella has written for Texas Co-op Power about performing with Wishbone the dog and taking a teenager through a haunted house, among other essays.


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