John Dillinger — Public Enemy Number One, killed in a theatre alley

On the night of July 22, 1934, federal agents shot and killed John Herbert Dillinger in the alley beside the Biograph Theater on North Lincoln Avenue in Chicago, ending a thirteen-month run that had made the Indiana bank robber the most hunted man in the United States. He had just left a screening of the gangster picture Manhattan Melodrama, flanked by two women, when agents of the Division of Investigation — the bureau that would soon be renamed the Federal Bureau of Investigation — moved in. As Dillinger reached toward a pistol and broke for the alley, three agents fired; three bullets struck him, the fatal round entering the back of his neck and exiting beneath the right eye. He was pronounced dead a short time later. He was thirty-one.

The trail to that alley had been laid by a paid informant. Ana Cumpănaș, a Romanian-born brothel madam known to the press as Anna Sage and miscast in legend as the “Woman in Red,” had told authorities where Dillinger would be in exchange for money and help against a pending deportation. She wore an orange dress that read as red under the marquee lights, a signal to the waiting agents. The deal bought the bureau its quarry; it did not, in the end, spare her, and she was deported to Romania later that year.

Dillinger had earned the manhunt across a frantic 1933 and 1934. Paroled in May 1933 after nearly a decade in Indiana prisons for a botched grocery robbery, he assembled a gang — among them Harry Pierpont, John Hamilton, Homer Van Meter and, for a time, the volatile Baby Face Nelson — and robbed a string of Midwestern banks. He broke out of the Lima, Ohio jail in October 1933 in an escape that left a sheriff dead, and on March 3, 1934 walked out of the supposedly escape-proof county jail at Crown Point, Indiana using, by his own later account, a pistol whittled from wood and blackened with shoe polish. Driving a stolen sheriff’s car across the state line into Illinois, he handed the federal government its jurisdictional hook.

The Bureau’s pursuit was not flawless. On April 22, 1934, a raid on the Little Bohemia Lodge in northern Wisconsin ended with agents killing and wounding bystanders while Dillinger and others escaped out the back. He underwent crude plastic surgery to alter his face and had acid applied to his fingertips to obscure his prints. None of it saved him. Named Public Enemy Number One and betrayed by an informant, he was run to ground outside a neighborhood movie house and killed where he fell — a founding legend of the modern FBI, and a sober study in how a fugitive’s own associates, not his disguises, tend to end the chase.