Unsolved Mystery: Jack, Cadillac Daddy and the Murder of Lillian

It was a date with death.

The youngest of the family’s seven children, Lillian shared her sister’s good looks but was a homebody, a bookish girl who friends said was willing to slap a boy who got too fresh.

On the night of the date, a Tuesday, Jack pulled up in front of the family home and sounded his car horn, and Lillian gathered her things. “I wonder what this goof looks like,” she said to Mildred as she breezed out the door. It was the last time Mildred would see her sister alive.

The family knew something was amiss when Lillian didn’t come home later that night. She was not the type to run off, and she’d never spent a night away from home before. But police believed she’d eloped with the young man. Nearly two weeks went by before they began to suspect foul play. Meanwhile, Mildred had struggled in vain to recall the details of her car ride with Jack. He’d mentioned his last name, but she couldn’t recall it. All she could offer her panicked family was a vague description of the man.

On Nov. 5, over three weeks after Lillian went missing, her battered body was found partially submerged beneath the Bluemound Bridge – which crossed the Fox River in Waukesha County. She’d been beaten and choked to death, her skull fractured in four places. Wounds on her hands indicated she had resisted the attack, and the scarf used to strangle her still clung to her neck. An autopsy confirmed she was dead when she hit the water and was most likely murdered shortly after departing the Graef home. According to the examination, she had not been sexually assaulted.

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Milwaukee’s Unsolved Mysteries and Hidden History


Police now intensified their search for the mysterious Jack, but not necessarily as a suspect. While Jack had called the Graef home on the day of the murder, so did someone else who spoke to Lillian. The family didn’t know the nature of the call, but detectives were working on a theory that both Lillian and Jack had been the victims of a third party, a mysterious man.

In search of him, investigators looked into an older man who’d regularly visited Lillian at her job at the Ramhorst Candy Store on North Third Street. Between 40 and 50 years old, the man was bald and paunchy but a fancy dresser and drove a dark Cadillac, a model similar to the car driven by Jack. Lillian sometimes called him “Cadillac Daddy,” and he typically stopped in on Tuesday and Thursday, including the day when Lillian was killed. After that, he never returned.

With a manhunt underway for both Jack and “Cadillac Daddy,” another killing on a back road sent the city into a panic. Three days after Lillian’s body was found, an assailant brutalized a married couple, Alvin and Emma Greenwald, on Highway 18, just a few miles from the bridge. Alvin had been beaten badly, and Emma raped and strangled. The panic subsided once police pressed Alvin on his muddled recollections of the evening, and he sobbingly confessed to staging the entire incident. Deeply in debt, he’d hired a man to kill Emma so he could collect on her life insurance policy. His own injuries had been self-inflicted.

Police followed dozens of other leads and questioned suspects caught in a dragnet that stretched from Chicago to St. Paul. But they were no closer to solving the crime.

In January 1928, police took the extraordinary step of ordering every man in the city who owned or had use of a Ford coupe – believed to be the make of Jack’s car – at the time of the murder to report to the central station for questioning, some 7,000 potential suspects. For weeks, Mildred had the grim duty of viewing these men, as many as 300 in a single evening, in an effort to find Jack. One man, a 26-year-old from Minneapolis recently arrested and charged with rape, was of particular interest. He’d been living in Milwaukee the previous fall, had access to a coupe and had left the city three days after the murder.

After Mildred picked his photo from a lineup, saying he looked like Jack, police put both of them together in a coupe, with the man driving, in a bizarre re-enactment. Under police guard, he drove the same route she and Jack had taken in October. Afterwards, she told police, “I am thoroughly convinced this is not the man.”

Over the next several years, police would periodically call Mildred in to look at a new suspect, and each time, she would shake her head. After calling a 1931 suspect a “dead ringer” for Jack, she backtracked and conceded that after multiple years, it would probably be impossible for her to positively identify the man. Still, police continued to check into leads as late as 1938 but came no closer to finding Jack or Daddy. The case remains unsolved.

‘Unsolved Mysteries & Hidden History’ appears in the May 2018 issue of Milwaukee Magazine.

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