McDonald was Chicago’s gambling king, and a Democratic Party king-maker. He had been for decades. But as McDonald grew older, he’d sought a veneer of respectability. He moved from the working-class West Side to a mansion on fashionable Drexel Boulevard. And he shed his first wife in favor of a rabbi’s daughter named Dora Feldman, thirty years his junior.

Time passed. Dora grew bored with her husband. She took up with a decorative young man a dozen years younger than herself. His name was Webster Guerin. He called himself an artist.

About 10 o’clock on this particular morning, Dora arrived at Webster’s studio in a Loop office building. She seemed agitated. Webster took her inside one of the rooms to calm her. There was shouting. Then a single gunshot.

People came running. When the door was forced open, Dora was found standing over Webster’s body, screaming. A pistol lay on the floor. 

The police took Dora into custody. Now the questions began. 

Did Dora murder Webster? Did she kill him by accident during a struggle? Did Webster commit suicide? The gun was Dora’s–and it had been a present from Webster! 

Motive? Was Webster breaking off the affair? Or was Dora breaking up with Webster? Dora had given Webster money for years–was it blackmail, to keep their relationship quiet? How much did Mike McDonald know about his wife’s Cougar play? 

Old Mike stood by Dora. He went with the blackmail story. Dora had told him she was paying hush-money to someone, but said she could handle it. Of course, Mike had never dreamed it would turn out this way.

The gambling king used all his influence to delay a trial. Dora was placed in a private sanitarium. Then Mike’s health went into decline. By August he was dead. 

McDonald left $25,000 to pay for his wife’s legal defense, a princely sum in 1907. The money was well spent. When Dora was brought to trial for murder, it took a jury only five hours to acquit her. 

Dora Feldman McDonald eventually left Chicago. She moved to California, married a doctor, and lived quietly. She died in 1930.