Charles Batsell "Charlie" Winstead (May 25, 1891 – August 3, 1973) was an FBI agent in the 1930s–40s, famous for being one of the agents (along with Clarence Hurt and Herman "Ed" Hollis) who shot and killed John Dillinger on July 22, 1934, in Chicago, Illinois.
Biography
Early life
Charlie Winstead was born in Sherman, Texas on May 25, 1891. Before joining the FBI he engaged in various occupations, including decorated service with the US Army in World War I, working as a deputy sheriff in several Texas jurisdictions, and just before joining the Bureau, as a law clerk in the US Attorney's office in El Paso, Texas.
He joined the Bureau in July 1926.
As a member of the Dallas Field Office, Winstead took part in several unsuccessful manhunts targeting outlaws Bonnie Parker and Clyde Barrow, and played a key role in the manhunt for kidnapper George "Machine Gun" Kelly; along with Agent Gus Jones, Winstead arrested Kelly's associate Harvey Bailey in Rhome, Oklahoma, which set the FBI manhunt for Kelly in motion.
John Dillinger
In May 1934, Winstead and several other Western agents, including former Oklahoma City policemen Jerry Campbell and Clarence Hurt, were assigned to the Chicago Field Office to help apprehend John Dillinger and his gang of bank robbers. After the Little Bohemia fiasco in April, in which agents led by Melvin Purvis and Sam Cowley had killed a civilian and lost an agent in a failed ambush of Dillinger's gang, FBI Director J. Edgar Hoover brought in the experienced Texans to augment Purvis's still-relatively inexperienced agents.
Winstead is widely believed to have been the agent who fired the fatal shot into Dillinger during the FBI's ambush at the Biograph Theater, shooting him in the back of the head at close range. For this, he received a personal letter of commendation from Hoover.
After Dillinger's death, Winstead helped track down Dillinger's former gang mate Lester Gillis/Baby Face Nelson, narrowly missing a confrontation with Nelson when he and Nelson drove past each other on a rural Illinois road. Winstead's encounter with the outlaw ultimately led to Nelson's showdown with the FBI outside Barrington, Illinois, in which both Nelson and Agents Cowley and Hollis were fatally injured.
Later career
Winstead returned west after Nelson's death, serving at the El Paso and Albuquerque offices. While in El Paso he took under his wing a rookie special agent named William C. Sullivan, mentoring him and helping to launch a career that would ultimately make him one of the top figures at FBI headquarters in Washington, DC.
Sullivan later characterized Winstead as a man with a "naturally probing mind" which could readily "absorb, retain, and use information." Although his formal education was minimal, the college-educated Sullivan remembered Winstead as "so well read that he stood out in sharp contrast to most men with college and graduate degrees, those who stopped learning when they left school."
In an organization which demanded blind obedience to its iron-fisted leader, Winstead was privately dismissive of FBI Director J. Edgar Hoover, confidentially telling William Sullivan never to initiate a meeting with him for any reason, since the mercurial Hoover was known to end careers on the slightest pretext. He told Sullivan:
"If Hoover ever calls you in, dress like a dandy, carry a notebook, and write in it furiously every time Hoover opens his mouth. You can throw the notes away afterward if you like. And flatter him. Everyone at headquarters knows Hoover is an egomaniac, and they all flatter him constantly. If you don't, you'll be noticed."
Shortly thereafter in 1942 Winstead himself came under the spotlight's glare, earning Hoover's stern disapprobation for having insulted a female reporter and accused her of Communist sympathies.
Hoover demanded an apology and as punishment ordered Winstead's transfer to the Oklahoma City field office. Winstead instead refused this forced relocation, telling Hoover to "go to hell" and resigning on December 10, 1942 — four years short of having accrued sufficient tenure for government retirement.