The woman in red wore orange

R. Marc Kantrowitz, BridgeTower Media Newswires

As he lay dead in the alleyway by the Biograph Theater in Chicago’s North End, onlookers rushed forward to dip their handkerchiefs in the still-flowing ruby red blood of Public Enemy No. 1.

Although his career lasted a short time, during which he and his gang robbed more than a dozen banks, netting over a quarter-million dollars, the now-dead 31-year-old John Dillinger had managed to capture the attention, if not the hearts, of the public.

Many felt a certain allure and sympathy for a robber of banks, which they saw as malevolent institutions: the real robbers that unfairly stole the homes, cars and possessions of those brutalized by the Great Depression.


John Herbert Dillinger was born in Indiana in 1903 to a grocer father who was harsh with his discipline and a mother who would die four years later.

John eventually moved in with his older sister and her husband and their growing family for several years, before returning to his father and his new stepmother. A bright and neat student, he liked reading. He had, however, a rambunctious side that soon led to petty theft and fighting and dropping out of school in the eighth grade. Mischievous, he once lassoed the outhouse of a neighbor and tied it to a passing train.
Dillinger enlisted in the Navy only to desert when his ship docked in Boston. Returning to Indiana, he met and married Beryl Ethel Hovious, but still could not lead a settled life.

He robbed a local grocery store, was caught, and pleaded guilty with the expectation of receiving a lenient disposition. Instead, he was slammed with a 10- to 20-year sentence. The experience shaped his life.

Embittered at the harshness of his punishment, he went to jail intending to improve his criminal skills — which he did, meeting and gathering his future gang. After serving nine years, he was paroled in May 1933. In 14 tumultuous months he would be dead.

Meanwhile, he robbed his first bank five weeks later and soon escalated that to one a month. He also met another love, Evelyn “Billie” Frechette, a waitress in Chicago.

Stylish and cool, Dillinger cut a dashing figure. He raided police stations to steal guns; hurtled over bank booths to grab money; and even haunted his nemesis, Detective Matt Leach, sending him post cards (“Wish you were here”) and calling him shortly after Leach innocently walked down Capitol Avenue (Dillinger asked how he liked the stroll).

He attended baseball games at his beloved Wrigley Field in Chicago knowing that the police who were chasing him would also be in attendance. He was so open and bold that he quickly caught the attention of the feds and J. Edgar Hoover, who dubbed him Public Enemy No. 1.

The chase was on. It would not last long.


Dillinger branded himself a bank robber, not a killer, as he believed it gave his profession a bad name. That all changed in January 1934, when he returned the fire of a police officer responding to a bank robbery. The stakes rose now that he was a cop killer.

Feeling the heat, Dillinger fled, hoping to make it to Mexico. He got as far as Arizona when he was caught. Though he was wanted in three states, Indiana won the right to prosecute its problem child. The prosecutor, Robert Estill, smiled proudly with his also-grinning prey, like two friends chatting amicably. Little did Estill know what his prisoner was plotting.

Charming his jailers, Dillinger bided his time before escaping, using either a gun that was smuggled in or the whittled replica of one. Singing as he gathered his non-threatened hostages, he waltzed out of the prison and jumped into the warden’s car to make his getaway, traveling to South Dakota and Iowa to resume his bank robberies. He even took time to travel home to Indiana with Billie to attend a family reunion.
Returning to Chicago, he barely escaped his pursuers. Instead, Billie was arrested. He would never see her again. Dillinger retreated to an inn in Little Bohemia where federal agents, who were hot on his heels, tragically mistook three innocent men coming out of the establishment and opened fire. One was killed, two wounded.

President Roosevelt took to the airwaves in one of his heralded “fireside chats” to decry the brazen lawlessness of the criminal Dillinger. A flood of crime bills quickly passed.

In Chicago, Dillinger sought the services of a plastic surgeon and altered his facial appearance and fingerprints. Traveling to South Bend, his last bank robbery was a sloppy one, with another police officer killed and a bystander wounded.

He also had a new girlfriend, the prostitute Polly Hamilton, who would prove to be his downfall. Polly’s madam, Anna Sage, nee Ana Cumpanas, had a legal problem. Facing deportation back to her native Romania due to her low moral character, she decided to cut a deal. Calling agent Melvin Purvis, she proposed receiving the reward money and being allowed to stay in the country. In return she’d deliver Dillinger.

On July 22, Anna, Polly and Dillinger decided to go to the movies. Shortly before, Anna excused herself to go to the store, where she called Purvis. Given the Bohemia fiasco, Purvis wanted to be sure that he got the right man. Anna agreed, and a plan earlier hatched was put in motion. How could Purvis not recognize the man with the woman wearing the bright orange skirt and white blouse?

The press — deciding that “red” rhymed with “dead” and connoted blood — changed the color of Anna’s orange outfit in reporting Dillinger’s death. The myth of the woman in the red dress continues to this day.

Over the following days, 15,000 people viewed Dillinger’s dead body. Billie did two years for harboring a fugitive. The government deported Anna.

Dillinger didn’t much like his last movie, “Manhattan Melodrama,” about a gangster starring Clark Gable.


R. Marc Kantrowitz, a retired judge, teaches law at Northeastern University and serves as a mediator for the Real Estate Bar Association. He can be contacted at The above column is based on the American Experience documentary “Public Enemy #1” and internet sources.