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Tag: charles winstead

The Abrupt and Fearless Character of FBI Special Agent Charles Winstead

By Larry Wack
Retired FBI agent

The role of FBI special agent, Charles B. Winstead in the shooting and killing of John Dillinger is widely known today. The 1934 incident outside the Biograph Theater in Chicago catapulted Director J. Edgar Hoover and the Bureau to the front pages during the “war on crime” and brought on a continuous wave of publicity for generations to come.1 Over the decades, crime enthusiasts would label Winstead and others chosen of that era as “Hoover’s hired guns.”

Winstead’s personnel file, recently obtained from the FBI under the Freedom Of Information Act, paints a colorful portrait of a man seemingly in contradiction to the polished lawyers and accountants hired at the time by the Bureau. Some might believe he should have been born decades earlier than the 1890s, and walked the dusty streets of places like Tombstone instead of the cement sidewalks of twentieth century Los Angeles, Chicago and surrounding.

Unlike the tall, mysterious character played by actor Stephen Lang in the movie, “Public Enemies,” when Winstead entered the Bureau in 1926 he was only five feet, seven inches tall, weighing one hundred thirty pounds. When he left the Bureau in 1942, he weighed the same. In reality, there was nothing mysterious about “Charlie” Winstead.

1 For purposes here, “FBI” & “the Bureau” are synonymous. In order not to confuse readers with the name changes that occurred, we use “FBI” overall during the early years but recognize that the name did not become official until 1935.

For Winstead, the label of “hired gun” isn’t applicable if taken literally. Unlike the hiring of other legendary agents during the early 1930s, Winstead’s file reveals nothing indicating he was originally recruited in 1926 due to his abilities with a handgun. In fact, there’s no mention in his background investigation regarding his handling of weapons, one way or the other.

Education wise, he only finished the 8th grade and for a few short years, attended the Sherman, Texas School for boys and the Sherman Business School. He held no formal educational degrees of any sort unlike the many lawyers and accountants hired at the time. More importantly for the Bureau during those early days is that his background revealed his years of investigative experience with the U. S. Attorney’s Office in El Paso, Texas. With that position came his extensive knowledge of federal law, writing indictments, court procedures, and rules of evidence. Everyone interviewed for his background praised Winstead’s work ethics and his moral character. One Bureau official who knew him agreed he could pass a bar exam whenever he wanted.

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