Her ex-husband Oliver Debrow born Durborrow was equally notorious. He had a rap sheet as long as a player piano roll, having been arrested regularly for drunkenness, assault, vagrancy and burglary. In he was apprehended in Dallas by a detective who had tracked him down there after a boxcar burglary in Galveston. Another time he was accused of beating up a railway worker, which was ironic considering his father was a railway switchman.
Another time he was nabbed stealing lead from a Methodist church's windows. The name Durborrow might be prophetic, as it stems from an Irish term meaning "a place of burial entered by door or gate. He also had a hard time keeping any job. He started off as a messenger for a postal service, then as a newsboy for one of the local papers.
By , when he married Jessie, he was a teamster for an ice cream company. But then the theater bug bit him. Sporting blackface, suitcase shoes, suspenders and an oversize hat, Ollie was praised for his broad physical humor and quick timing. Reports on how Ollie first met Jessie varied. One columnist said she was a waitress in Houston when Ollie walked in and cajoled her into joining his troupe.
She may have been all those things. But Ollie would later state under oath that he met her at the Princess Theater where she was a dancer in the chorus. She was only fourteen. Her name then, he said, was Jessie Rogers. Perhaps this was a stage name since on her wedding license her name is given as "Jessie May Richardson. A handwritten entry in the church ledger confirms the spelling of her name and gives as their witness W.
Kyle, an electrician who was out on bail having shot a flatmate a few days earlier because he made advances on his wife. He was an ironic choice considering the shooting scandal that was soon to engulf Ollie and Jessie.
