The unlikely sheriff

Michael Hennessy has battled through controversies and cop culture to create the most progressive Sheriff's Department in the nation


Michael Hennessey has served as San Francisco's sheriff for half of his life, the longest such career in California history — and by all accounts the most progressive. Since taking office in 1980, Hennessey has been an island of liberal enlightenment in a political climate and law enforcement culture where tough-talking conservatism has been ascendant.

Yet in that era, Hennessey pioneered the creation of innovative programs to compassionately deal with drug abuse, violence, recidivism, and lack of education among jail inmates. He proactively brought unprecedented numbers of minorities, women, LGBT employees, and ex-convicts onto his staff. And he sometimes resisted carrying out evictions or honoring federal immigration hold orders, bold and risky social-justice stands.

His stances drew scorn from the local law enforcement community, which never endorsed him in contested elections, and criticism from political moderates and national media outlets. But San Francisco voters reelected him again and again, until he finally decided to retire as his current term ends next month.

He credits his success and longevity to the people of San Francisco, who have also bucked the harsh national attitude toward criminals and the poor. "San Francisco is still largely a liberal voting town," he told us in his well-worn office at City Hall, "and not many liberals run for sheriff."

That logic held up in this year's election when progressive Sup. Ross Mirkarimi — Hennessey's hand-picked successor — was elected to the post. Mirkarimi, who led a tribute to Hennessey at the Dec. 13 Board of Supervisors meeting, said he's honored to be able to continue the legacy of someone he called "the most innovative sheriff in the United States."



Hennessey was a 32-year-old Prisoner Legal Services attorney for the Sheriff's Department in 1979 as he watched then-Sheriff Eugene Brown letting go of reform-minded staffers and ending his predecessor Dick Hongisto's early experiment with a school in the jail. So Hennessey quit his job and focused on running for the office.

"I said to myself that I'm not sure if I'll be a good sheriff or not, but I know I'm better than anyone else running," he told us, later adding, "I certainly never expected to be sheriff for 32 years."

Rank-and-file deputies — with whom Hennessey has periodically clashed throughout his career — always preferred one of their own in the job. "As seen in this election, they would like to see someone coming from their ranks," said Hennessey, even though he notes that at this point, he has hired all but three of the department's nearly 1,000 employees.

But Hennessey's outsider status allowed him to deal with the inmate population in a way that the average San Franciscan appreciated, even if the average cop didn't. "When you're in law enforcement, all you see are criminals, victims, and people in law enforcement. But I would talk to all kinds of people in the community," Hennessey said, noting that his experience as a jailhouse attorney gave him a holistic view of his job. "I worked in the jail and I got to know prisoners as people."

They were people who had certain needs and problems, such as substance abuse, a common problem among criminals. And they were people who would be returning to society at some point, as Hennessey constantly reminded those who expected prisoners to be treated harshly or simply warehoused.

So he broke down the wall between the jail and the community, bringing the city's social service providers and educators to work programs in the jails, and developing anti-recidivism and vocational programs that allowed ex-offenders to re-engage with the local community.

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