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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.

Although Win stead’s initial roots in Texas probably acquainted him with handguns and rifles, his FBI application also reveals he had prior law enforcement experience as a local peace officer for the period 1911-1912 in Brownsville, Texas. His shooting abilities were really not recognized by the Bureau until years later in the early 1930s when the “war on crime” escalated and carrying firearms was paramount for all agents. Only then did he seem to rise above many others in having a “special need” that the Bureau was desperately seeking.

A 1934 inquiry to the field by FBI headquarters placed Winstead on a list who had unique abilities to handle cases involving the dangerous desperadoes of that violent period. He wasn’t the only “marksman” on that list and he wouldn’t be the last, but at the time, he was the only man his Dallas Special Agent-In-Charge (SAC) recommended from that office. 2 That alone would be a label that would follow him throughout his Bureau career.

Among the many who were interviewed about Winstead during his background investigation, the legendary FBI SAC, Tom White, said he had known Winstead for

2 The entire list is set forth in a June 12, 1934 memo, FBI file 66-3760-972

several years and his reputation was beyond reproach. White added “Winstead’s only handicap is that he does not have an impressive appearance, is small in stature and has no outstanding personality.” White commented that he thought some of this could be overcome. In another interview, SAC Gus Jones, who also handled much of the Southwest, would also praise the work of Winstead clearly recommending him for the agent position.

On July 27, 1926, Bureau headquarters received a “decoded” telegram from Bureau SAC Ralph Colvin in El Paso, Texas. It was a brief message to the Director which read “Chas. B. Winstead appointee took oath and left for Oklahoma City today.” As a reminder, there wasn’t any training to speak of for FBI agents during those early times.

Within a year, Winstead would be submitting his first wave of explanations to Director Hoover as to why his “status reports” on numerous cases were not completed or were long overdue. His superiors at his previous position with the U. S. Attorney’s Office rated his typing and reporting as way above average but obviously he’d have to get accustomed to the many deadlines demanded in the Bureau. His file reflects that his report writing would need to be monitored by superiors for years to come.

In general, Winstead’s file reflects that by the end of the 1930s, he had survived the wrath of FBI headquarters on quite a few occasions while always marching to his own drum. Early on, he was the holder of two disciplinary transfers. He was also subject of unfounded allegations he beat a prisoner with brass knuckles. On one occasion, he arrested the wrong person as a fugitive and inflamed the situation by using an anti- Semitic comment toward the suspect. He drew a three day suspension for drawing his weapon on a citizen during a verbal altercation. While in Chicago, he struck a delivery man who called him an sob over a parking place. His approach to citizens and witnesses in areas outside the Southwest would be characterized as gruff and complaints were common. A later superior would describe Winstead as having the “Texas approach….”

With limited space to discuss all of them, FBI “efficiency ratings” of Winstead by superiors were not overly complimentary at times during his career. There was a general consensus that his uncaring personal image, his abrupt personality and overall insensitive approach fell short of expectations desired by SAC’s and others. For other reasons, Winstead’s superiors realized they’d have to live with it all.

Although now a five year veteran of the FBI, a 1931 “rating” by SAC Reed Vetterli in Birmingham mentioned “There are certain things about him that are likable, and on the other hand there are characteristics that are not palatable.” Vetterli noted that Winstead’s investigative work was satisfactory but was critical of his “slovenly personal appearance. During the summer months he continued to wear the same blue serge suit, and an old dirty felt hat…” Vetterli continued “…he likes to impress people with the fact that he was born out west, and frequently talks about the West. This is not particularly desirable when an agent is in another part of the country.”

During that same year, Assistant Director Harold Nathan added his comments to Vetterli’s rating and wrote in part, “[Winstead] is a likable chap. He does pose as a Westerner. However…he is now in a section of the country where the distinct southern pose is more rabid than any western pose. ….If I knew him better I would endeavor to get that western foolishness out of his mind…Under no circumstances do I think he should be catered to.” !

A “rating” in 1932 by SAC Blake in Dallas revealed “This is a good all around agent. Winstead does not present any outstanding qualities. He appears to be of the faithful, plodding sort of individual, capable of rendering satisfactory services under all circumstances, but without any demonstration of unusual ability in any line. His personality is fair. He demonstrated an unsatisfactory knowledge of the Manual of Rules and Regulations.”

In November 1934, FBI Inspector Samuel Cowley rated Winstead (and others) while in Chicago during the course of Cowley’s routine administrative duties. Cowley wrote, “…Winstead is a typical Texan. He does considerable whining and complaining, which seems to be a part of his nature and makeup. He discounts the value of most all leads, and has continuously requested to be sent back to Dallas, Texas…and has repeatedly advised of the expense to which he has been put by being transferred to Chicago and his dislike for same.

He played an important role in the killing of Dillinger, having fired three shots and was calm and deliberate…and seemed particularly proud of it, which is probably only human. The attitude, however, which was taken by the other two men who also fired shots were never heard to comment on same, impresses the writer as being more commendable.” 3

Still on “special assignment” in Chicago during the 1935 period, Inspector E. J. Connelley wrote Winstead was “an average agent without any particularly outstanding characteristics. [He] is one of the slowest-thinking agents in the Chicago office and is not of any particular value, except for his marksmanship.”

SAC Ralph Colvin later wrote that Winstead “was a sober, industrious agent with one idiosyncrasy …….He likes to attract attention to himself by appearing as a two gun Western bad man… at times tyrannical with the employees.” Colvin commented that unlike those agents who normally donned the “straw boater” of the day, Winstead often wore a ten gallon hat in the office. He added that Winstead carried two engraved hand guns and usually sat with his feet on the desk when in the office.

At times, superiors thought Winstead was “tactless and uncouth,” and some were not overly anxious of his participating in cases where he’d be in contact with bankers, businessmen, and corporate types. Most agreed he had “no executive ability,” and that would mean he’d spend the rest of his career at the street level, never rising to any position of supervisory authority. Perhaps that didn’t phase Winstead to any degree…as long as it could be back in Texas.

Winstead’s initials are seen on the “efficiency ratings” forms throughout the file so he did see them prior to them being sent to headquarters and eventually his file. Whatever went back and forth between him and his superiors about them, we’ll never know. There are occasional thoughts in reviewing them that perhaps Winstead couldn’t have cared less. We can only wonder if he really even read them before scrawling his initials on them.

3 Two other agents, namely SA Clarence Hurt and SA Herman Hollis also fired at Dillinger; Winstead no doubt fired the actual fatal shot(s), one of which entered from the rear & exited the right cheek area.

The trade off with Winstead’s sometimes “unpalatable” persona came in the form of other attributes that some lawmen would argue are more consequential. His career ratings remained as “satisfactory” throughout, generally scoring in the 80s and 90s overall. He was ambitious and many times a workaholic. He had a keen street sense in ferreting out dangerous fugitives, and dealing with street urchins.

Wherever he went, from beginning to the end of his career, local law enforcement fell in love with the man and letters in the file, along with comments from supervisors attest to that. Winstead had the ability to relate to the sometimes uneducated local lawmen of the day, and was one who realized early on that their assistance was paramount to any Bureau agent worth his salt. After all, having spent time as a local peace officer, Winstead had been there.

In 1933, SAC Blake in Dallas enhanced his rating from a year before writing, in part, “An agent who fills well the duties involving hardened and dangerous criminals. Has long been accustomed to the use of firearms with which he is very familiar. He is courageous and in the main, uses good judgement.”

With firearms training still in its infancy in the early 1930s, knowing his abilities, Winstead’s superiors were confident in sending him to the front lines not only because he was proficient with various weapons, but as one rating showed, “He doesn’t know the emotion of fear.” He handled the “tough guy cases” very well according to his Dallas SAC. It was his Dallas SAC who sent Winstead in pursuit of Bonnie and Clyde. Later his superiors assigned him the trail of “Machine Gun” Kelly, Harvey Bailey and major kidnappers among others.

While in Dallas during a yearly field office review, it was Inspector John Keith who wrote in the office ratings that he “considered agent Winstead far above the average as a field agent; that he is better fitted for assignment where he now works and one of his outstanding recent jobs was the procuring of the confession from Cass Coleman which led to the discovery of part of the Urschel [kidnapping] ransom money…”

In May 1934 Winstead, among others, was urgently sent to the Chicago office. In the fall, Assistant Director Harold Nathan wrote, “He was transferred to Chicago last spring, in order to perform gun work in the Dillinger and other cases. So long as Winstead remains in Chicago he will be of little, if any value. I believe he should be sent back to the Southwest.”

Hoover disagreed with Nathan’s suggestion and on the memo, Hoover wrote, “Not until we get Van Meter and [‘Baby Face’] Nelson.” Chicago assigned Winstead to the Nelson case and we now know that on one November 1934 morning, Nelson sat in a muddied automobile at the end of Winstead’s rifle. 4

Only months later, Winstead was rushed to Florida with others to deal with “Ma” Barker and her son who were subsequently killed in a shootout with FBI agents.

“Gun work…” within the handful of relevant sections on early “efficiency ratings” forms, that one never appears. Nor does one appear for “tough guy cases”…

In a later rating of 1936, Nathan commented, “Winstead is well qualified in the use of all types of firearms and is consequently a desirable man for dangerous assignments. He is cool and entirely fearless…”

By 1941, Winstead was a household name in the Bureau. They tried using him as an instructor for training. FBI counselor B. Suttler wrote in one critique, “Winstead is so well known in the Bureau that the minute his name was called, the entire class started laughing.

Agent Winstead is such a character that he naturally goes over big.” Suttler continued, “Winstead, as soon as he arrived at the lectern stated very frankly it certainly was not of his choosing to be there. The writer doubts very seriously whether he should address groups as a Bureau rep as it is felt he not only does not care for this type contact with the public but might go too far and say something that would prove embarrassing to the Bureau.”

In 1942 as Resident Agent in Albuquerque, Winstead served under Delf A. “Jelly” Bryce. Bryce was hired by the Bureau with no formal education, no doubt because of his shooting abilities. When he arrived at the FBI in 1934, he had already killed several men. They were “two peas in a pod” but Bryce would soon learn that he really didn’t have the control of Winstead he thought.

4 This incident was at the Hermanson residence with SA James Metcalfe earlier in the day of the Cowley and Hollis murders. Winstead wasn’t sure of the identity of the auto occupant(s) who turned out to be Nelson in the company of his wife and John Paul Chase. He was observing from an upper window.

In one of the last ratings of Winstead in 1942 at the age of fifty-one, Bryce wrote that Winstead was one of the “old timers” in the Bureau. Bryce’s description in the ratings said, “Small in stature, wiry and has a definite ‘Texas’ approach and personality. Is somewhat gruff but good humored,…turns out a large volume of work and is a hard worker. He is reckless, abrupt, and forceful, and belongs to this section of the country.

He definitely should not be assigned to a metropolitan area. He possesses an abundance of intestinal fortitude and is especially adaptable for dangerous assignments. He is somewhat rough on new agents…” Importantly, Winstead was extremely loyal to the Bureau and all of his ratings indicate such.

It was soon after that rating that Winstead’s fall from grace with Director Hoover was in motion and some of the words of FBI counselor Suttler’s critique of Winstead and possibly saying something embarrassing would ring home.

Winstead’s comment he made to a reporter in 1942, while on duty, regarding the Soviets was a subject best left to the State Department and not the mis-spoken words of an FBI agent. It’s easily mis-interpreted that the opinion of one agent is the overall Bureau policy. The reporter complained to the Director. Bryce tried in vain to protect him from allegations by portraying the female reporter as a “screwball” adding that her editor even agreed with that. It didn’t work…

Rather than take a third disciplinary transfer, in this case to Oklahoma, Winstead chose to resign from the Bureau in December 1942. On the summary memo of the comments Winstead made to the reporter, Director Hoover wrote, “I was annoyed and shocked at the actions of Winstead in deliberately misrepresenting the true facts.” This comment came apparently as Winstead was trying to explain himself. Hoover also wrote to Bryce “Winstead was not disciplined for condemning communism but for comments in an official capacity re Russians…”

After resigning in December 1942 Winstead would join the U. S. Army and spend his remaining working days as a captain mainly assigned to intelligence matters. He’d later secure a position with the State Liquor Authority in Albuquerque, New Mexico working under retired FBI special agent, George Franklin.

In 1958, Assistant To The Director, William C. Sullivan – a good friend who worked under Winstead in El Paso – ran across him at a meeting in Los Alamos. In returning to FBI headquarters, Sullivan wrote in a memo to Director Hoover, “It was quite interesting to me to notice how his mind turns to the FBI and to the years spent with it investigating.

Three times during the conversation, Mr. Winstead asked that I remember him to the Director. He added that he supposes the Director doesn’t think very well of him now because he had resigned …which he knows he should not have.” Winstead was assured the Director held no animosity and Sullivan documented that. Whatever happened between Director Hoover and Winstead, it’s easy at times to believe it was “just business.”

In 1970, Hoover would send him a congratulatory letter for an award presented by his retired colleagues in Albuquerque. It would be addressed, “Dear Charlie.” It was nearly thirty years since the two of them had sparred over the Soviet comment.

In his later personal manuscript, Winstead reflected on his life in general and his FBI career. At the manuscript’s ending, he managed to keep pace with SAC Bryce’s earlier description of Winstead’s humor. The “old timer” who spent his last days under Bryce wrote, “I guess we all make mistakes occasionally. I know I made a lot of them and some of them were very laughable but I’m not going to say anything about them here….” Whatever the subjects of those laughable stories were, it appears that he and his colleagues have departed without leaving any clues as to their content…

(c) 2014, all rights reserved. Larry Wack is a retired FBI agent. He is not a spokesman for the Bureau, nor any active or retirement groups involving the FBI. He maintains a website reflecting his research into the early Bureau and the agents of the depression era currently at: www.historicalgmen.squarespace.com. A special hat-tip to Judge Shawn McCarver for his observations…

 


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