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Polly Hamilton and Dillinger, Part 1


Dillinger was likable as a kid – smart with good grades. Even at the time of his death, almost everybody liked him. He had a good sense of humor, was generous and was known by some as the “gentleman outlaw.” His mother died when he was only four, and his 15 year-old sister was put in charge of him while his father worked.

When Dillinger was in the sixth grade, he was hauled into juvenile court one day for stealing coal from the railroad yards to sell to neighbors. When the magistrate told him to stop chewing his gum, Johnnie stuck it on the bill of his cap and grinned. The judge told him his mind was crippled.

By age 20, Dillinger was a machinist and a better-than-average baseball player. One night he impulsively stole a car from a church parking lot; then fearing arrest, he enlisted in the Navy. He didn’t like it and went AWOL several times until finally being listed as a deserter. He went back home, got married, moved in with his in-laws and went back to baseball and poolhalls.

One night, Dillinger got drunk with a fellow baseball player and ex-convict, who persuaded him to help him rob a grocery store owner who, on Saturday nights, carried his receipts home with him. The robbery went bad, and the boys ran away. Dillinger was found-out and was advised to plead guilty and throw himself on the mercy of the court. His judge wasn’t impressed and Dillinger went to prison. Nine years later he came out a well-educated bank robber.

By 1934, Dillinger was Public Enemy Number One. It was about this time that he met 26 year-old Polly Hamilton, who had moved from Fargo to Chicago. When she wasn’t waiting tables, she worked the streets for brothel owner, Ana Cumpanas. Cumpanas was going by the name of Anna Sage, at the time, and was fighting deportation back to Romania for being an undesirable alien of “low moral character.”

Polly met John Dillinger at Chicago’s Barrel of Fun nightclub in early June. Dillinger introduced himself as Jimmy Lawrence, and they went dancing, to the movies, and to the amusement park. A few weeks later, they celebrated Dillinger’s 31st birthday at the French Casino nightclub.

Polly introduced him to Sage and, from a picture in the paper, Sage thought she recognized him as John Dillinger. She cut a deal to turn Dillinger over for the reward and no deportation.

Three nights later, Polly and Anna walked out of Chicago’s Biograph Theater with the man Polly knew as Jimmy Lawrence. Sage was wearing a bright orange skirt to identify herself, and moments later, Dillinger was gunned down in the street.

Hamilton went into hiding, claiming she had no idea Sage was going to betray them. When the FBI tried to find Hamilton, Sage told them Polly had gone back to Fargo. When they couldn’t find her there, they speculated that she committed suicide.

Stay tuned tomorrow for a different version of what might really have happened that night.

Dakota Datebook written by Merry Helm