SFCentric History: The Crazy Life of Federal “Lady Hooch Hunter” Daisy Simpson

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San Francisco is an old, iron safe filled with gold, glory, disaster, and secrets. SFCentric History is a column, by SF writer V. Alexandra de F. Szoenyi, that digs in the vaults of local history and shares the sensational people, places, and things that rocked San Francisco.

San Francisco always has had a cast of zany characters. For this week’s installment of SFCentric History, I will take a look at one of those characters in particular–Daisy Simpson, a woman who left a seedy past behind to become one of the few female Federal Prohibition agents, only to return to the other side of the law soon thereafter.

Photo: The National Archives, Pieces of History

Born in Dayton, Washington, Daisy Simpson gained notoriety as the woman Prohibition agent who used hundreds of disguises, a variety of aliases, and the guts to put away those violating the Volstead Act, and Prohibition law, which prohibited the “production, sale, and transport of ‘intoxicating liquors’. But just a few years before this, she was Daisy (also known as Verne) Simpkins, a troubled young lady in San Francisco, who found herself in a sanatorium, and attempting suicide. In 1917, she had problems with drugs, drink, and hanging with the wrong crowd. She was able to recover from her addiction, using the knowledge she gained from the other side of the law, to her advantage.

That same year, Daisy became an investigator for the State Law Enforcement and Protective League, in which she fought against prostitution in Sacramento and San Francisco by enforcing the Red Light Abatement Act. She also served as a member of the San Francisco Police morals squad during World War I. All of this was setting her up for the job for which she would become nationally known.

Photo: The National Archives, Pieces of History

While living at the Hotel Aldrich, at 439 Jones Street, Daisy Simpson decided to apply to become a Federal Prohibition agent of the Internal Revenue Prohibition Unit, on September 6, 1921. When she was accepted, Daisy Simpson became one of only 12 Treasury Department Prohibition agents that were female. Before then, women only served in the department as secretaries or in the capacity of assisting male agents with their missions.

Photo: March 19, 1923 Madera Tribune

Women proved to be a necessary component in nabbing bootleggers. Females disobeying the law would use to their advantage the fact that male agents searching them was seen as inappropriate, even illegal in some states, and would find ways to outwit their opponents, such as purposefully hiding liquor on their person. Agents like Daisy would be able to stop that from happening.

Photo: February 20, 1925 Sotoyome Scimitar

In addition to being able to outwit women by thinking like a woman, Daisy Simpson used a variety of skills to help her in her pursuits. She was known for her keen acting skills; she would pretend to be different people, and feign illnesses in order to catch criminals. In one sting, she pretended to faint outside a bar; when the bar employees gave her whiskey, she promptly arrested them. The February 20, 1925 edition of the Sotoyome Scimitar reported that in 20 days, Simpson had single-handedly made eight arrests, “confiscated 10,000 bottles of beer, sixty cases of gin, twelve cases of Scotch, and a large quantity of wines and other liquor.” As her jurisdiction extended to the Napa Wine Country, Daisy led raids in Santa Rosa and Valley of the Moon. One operation, in nearby Cloverdale, resulted in 8,400 gallons of pre-war vintage being poured at the Frei Brothers’ winery.

Photo: July 12, 1924 Healdsburg Tribune

At the end of the day, Simpson was no-nonsense and held her own. A raid at a saloon at 1114 Valencia Street found her holding off three men–who didn’t like it when they found out who she was–with a gun. In October of 1923, when Simpson was shot in the right shoulder during a raid, she refused to divulge any details (possibly to not implicate friendly fire by fellow agents), as she healed at the United States Marine Hospital.

Photo: March 22, 1922 Sacramento Union

For all her glory, Daisy didn’t always please judges, who felt she went a little too far with her pursuits, went mostly after insignificant offenders, and practiced entrapment to make some arrests. Nevertheless, Daisy Simpson fought those who fought Prohibition, from 1921 to 1925, when women were banned from serving as field agents. It has also been stated that Daisy was bedridden in November of 1925 with illness, which caused her to retire.  

The story could have ended there, with Daisy Simpson retiring, and living a peaceful life, but life doesn’t always work that way. Maybe, since she was no longer professionally on the right side of the law, slipping back to the other side once again proved easy. In May of 1926, Daisy was arrested in El Paso, Texas for receiving a package in the mail that contained narcotics, thus violating the Harrison Narcotics Act. She was incarcerated; after her pleading with friends, family, and even her estranged husband for bail, her pleas fell on deaf ears, a desperate and shamed Simpson shot herself in the abdomen with a gun she had smuggled in. The Santa Cruz Evening News ran a story with a headline that read, “Daisy Simpson Fast Approaches the End: Her Friends All Gone.” Other publications also preemptively told of her demise–of her life, and of her reputation.

Photo: March 22, 1926 Madera Tribune

How often one is counted out when one is only down. Although doctors only gave her a day to live, Daisy Simpson recovered in the hospital, with her sister by her side. Her sentence was suspended, and Daisy finally decided to live that quieter life. She married, had four children, and ran a motor home in the outskirts of Sausalito, before passing away at home on November 12, 1940. The Oakland Tribune, while speaking about her arrest and suicide attempt in the late ‘20s, made it a point to mention that Daisy was “one of the most daring women engaged in detective work In this country.” And she was. Whatever setbacks she had, Daisy Simpson was able to go from notorious to notable, while shunning society-accepted roles to do more for herself, and all women.

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V. Alexandra de F. Szoenyi

V. Alexandra de F. Szoenyi

V. Alexandra de F. Szoenyi is one of those rare born-and-raised San Franciscans (unicorn status). She is the Style & Culture, SF Editor for Hip Latina, and writer for several publications on fashion, art, culture and all things San Francisco. Alex aims to educate everyone (including natives) on anything you could possibly want to learn about the best city in the world. Follow her at @SFCentric and @TheItFactorBrand.