Vicki Hennessy at her Westside home. (Joel Engardio/Special to S.F. Examiner)

The woman who would be sheriff

Everything I know about women’s prisons I learned watching the Netflix hit “Orange is the New Black.” So it was tempting to ask Vicki Hennessy — a candidate for sheriff who began her career in 1975 guarding the women’s jail in San Bruno — how real the show is.

“A lot of it rings true. Inmate Red is a compilation of many characters I saw in the old days at the jail,” said Hennessy, who binge-watches like the rest of us. “Everything is just condensed for entertainment value. It’s the same with ‘Game of Thrones,’ but I like to think San Francisco politics are not quite that bad.”

Hennessy’s assessment is technically correct. We don’t chop heads and display them on sticks at City Hall. Yet alleged crimes, attempted political assassinations and high drama have defined the sheriff’s office in recent years.

Days after taking office in 2012, Sheriff Ross Mirkarimi was charged with domestic violence battery for bruising his wife’s arm. When Mirkarimi pled guilty to a misdemeanor of false imprisonment, Mayor Ed Lee suspended him without pay and made Hennessy the acting sheriff.

Hennessy became the first woman to serve as sheriff in San Francisco. She had 36 years of experience with a resume that included the ranks of sergeant, captain, chief deputy and commander. She also directed San Francisco’s Department of Emergency Management.

But Mirkarimi was reinstated six months into Hennessy’s time as sheriff. The Board of Supervisors failed to permanently remove Mirkarimi from office for misconduct. His wife, Eliana Lopez, stood by his side and became the star of a one-woman play based on her ordeal called “What Is the Scandal?”

Now Mirkarimi is running for re-election, and Hennessy is asking voters to give her the job for real.

“I returned stability to the department as interim sheriff,” Hennessy said. “My hope was that Mirkarimi would have continued the stability and put the department before himself. I tried to give him a roadmap. But leadership has to be earned, not claimed.”

Both Hennessy and Mirkarimi support San Francisco’s Sanctuary Ordinance, the political lightning rod that gives due process protections to undocumented immigrants facing deportation. Yet Hennessy said limits imposed on local law enforcement should be reviewed to ensure people with serious criminal records receive heightened scrutiny. 

“With me, you’ll get earned leadership,” Hennessy said. “I’ve always held myself and those reporting to me accountable.”

Hennessy, 62, is a native Westside San Franciscan and Lowell High School graduate. Her parents split up when she was 6.

“My step-father wasn’t a good guy. He was alcoholic and verbally abusive,” Hennessy said. “Our society needs to realize there isn’t a family untouched by mental health and addiction issues.”

Hennessy left home at 18 for a short-lived relationship with an unemployed actor.

“I thought I was in love but we were young and immature,” she said.

College was something Hennessy did while working. She never received a degree but accumulated about 130 credits from several different schools.

At 22, she heard that the Sheriff’s Department had started recruiting female deputies for equal pay and assignments.

“I took the test off the street and ended up in a few scenes of history,” said Hennessy, who witnessed many of the tumultuous events of 1970s San Francisco while on the job. “I wasn’t the wide-eyed Mary Ann Singleton everyone was reading about in ‘Tales of the City.’”

Hennessy found love with mounted police officer Jim Hennessy. They have been married 39 years and have two adult children.

“Jim was on the horse when I met him and he looked good,” said Hennessy, who would professionally outrank her husband through competitive testing and become a pioneer for women and mothers in uniform.

“I don’t mind staying home and making dinner,” said Jim Hennessy, now retired. “It’s time to have a woman sheriff, and Vicki is the most qualified because she’s already
done it.”

Joel Engardio lives west of Twin Peaks. Follow his blog at Email him at

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