When he took his seat on the San Francisco Board of Supervisors, Gavin Newsom wasn’t exactly the left-leaning stalwart who would emerge two decades later as the front-runner for California governor.

Newsom’s appointment in 1997 was viewed as providing a dose of moderation to the liberal board. A 29-year-old wine and hospitality entrepreneur backed by Getty oil fortunes and the city’s political elite, he described himself as a “dogmatic fiscal conservative and a social liberal.” So rare was his profile in the diverse, rough-and-tumble world of San Francisco politics that a story in The San Francisco Examiner began like this: “The straight white male quota on the Board of Supervisors has been met.”

He ascended while enduring the kind of rigorous vetting that can only be applied in one of the toughest liberal laboratories – a city Sen. Dianne Feinstein, also a former mayor, once warned “will roll you 67 ways to Sunday.”

Click to resize

Like Democrats before him, who in other parts of the country were considered outrageously liberal, Newsom repeatedly irritated his party’s left, which looked askance at his pragmatism and his opposition to tax increases. Advocates for the homeless assailed his plans, dismissing him as an elitist with little notion of what it meant to be poor. They called him conservative and pelted him with cream pies for being “pro-development,” as they put it then.

His aides saw the characterization as unfair, arguing that his real role in San Francisco was as a change agent.

Yet even after he became nationally known for his liberal bravado, beginning with his trailblazing push for gay marriage, Newsom as mayor never shed the label of “pro-business Democrat.”

Now 50, after his seven years as lieutenant governor – a position with few built-in responsibilities – a different Gavin Newsom has emerged in a state where Democratic Party priorities are beginning to look more like San Francisco’s.

A review by The Sacramento Bee found Newsom has shifted his positions to the left on issues ranging from sanctuary cities to high-speed rail and charter schools. Some of the changes have made him vulnerable to the critique that he’s flip-flopped.

Newsom declined repeated requests for interviews for this story. To his supporters, the candidate remains the same liberal problem solver who allowed same-sex marriages and championed gun control and legal weed. They contend he takes a big-picture approach and spans insular party divides. And they also stress that he has taken the most liberal positions in the governor’s race.

“Leadership is measured by results – and Gavin Newsom’s mayoral administration was universally pro-labor, pro-consumer, pro-teacher and pro-environment and achieved the highest minimum wage, the most generous worker and renter protections and the only citywide universal health care plan in the nation – to say nothing of igniting a national movement for marriage equality,” spokesman Nathan Click said in a written statement.

“He has continued this record of courageous, progressive leadership as lieutenant governor by championing historic criminal justice reforms, environmental protection, and gun safety efforts. Anyone suggesting otherwise is ignoring history and obvious facts.”

Newsom’s current platform includes government-run, universal health care, full-service community schools open every day and a state bank to finance infrastructure, small businesses and the marijuana industry he helped legitimize. The policies he favors, ripped from liberal wish lists, would add significant costs to the state budget. He’s been endorsed by organized labor’s heaviest hitters, including groups representing hundreds of thousands of nurses, firefighters and teachers.

As a candidate for mayor, however, Newsom touted the successes of charter schools and got backing from their proponents. “Charter schools provide an opportunity for parents, community leaders and other education entrepreneurs to explore new and better ways of reaching and educating our youth,” read a policy paper from his first mayoral run.

The California Teachers Association, no fan of charter schools, in its endorsement questionnaire for the governor’s race asked each of the candidates whether they think the number of charter schools in the state should increase. When asked by The Sacramento Bee, spokesman Nathan Click confirmed that Newsom answered “no” in winning the organization’s endorsement.

Later, Click added that he “has always supported charter schools as laboratories of education but doesn’t believe the state should approve more until there is real oversight and stricter enforcement.”

As mayor, Newsom’s plans for city workers and public schools weren’t always in sync with their interests. His proposed $5 billion budget for 2004-05 called for privatizing an inmate health program, a move that threatened the layoffs of more than 100 city workers.

His spending plan also included a proposal to outsource laundry services at Laguna Honda Hospital. By putting the jail health program out to competitive bid, according to a San Francisco Chronicle article on Newsom’s budget release, the mayor was hoping to save up to $4.5 million during the second half of 2005. The changes were not in the budget he signed, though Newsom’s administration did reach a laundry deal with SEIU later, in 2009.

Newsom’s camp says the laundry plan, and similar budget maneuvers, were recession-driven efforts. They note he didn’t move to privatize major departments and facilities, such as the airport, hospital and transportation agency.

The Sacramento Bee review also found other instances in which Newsom shifted:

▪  Republican donations: Last year, Newsom’s campaign unloaded on rival Democrat Antonio Villaraigosa for speaking at a local chamber of commerce function in Fresno, jabbing at him because the group gave money to Republican candidates.

But in 2000, running unopposed for San Francisco supervisor, Newsom paid $500 to the city’s Republican committee, which allowed him to appear on a GOP-backed slate mailer promoting his campaign, along with the campaign of George W. Bush. Newsom was endorsed by the Republicans, along with a ballot measure he backed setting customer service standards for city workers.

He received no GOP endorsement for the 2003 mayoral run, but Republicans worked on his behalf, setting up a phone bank and sending out a mailer casting him as the preferred candidate. A local GOP vice chairman, Jim Fuller, told The New York Times that an informal survey of Republicans, including absentee voters and those at the polls, found that 85 percent voted for Newsom.

“If it hadn’t been for us,” Fuller said at the time, “he wouldn’t have won it.”

▪  Bail reform: Newsom now wants to eliminate bail in California and was the only statewide elected official to sign on to 2016 legislation that would have overhauled the system. But in San Francisco, he pressed to raise bail to bring it more in line with other Bay Area counties. He signed a 2002 resolution that argued those suspected of drug crimes there found it easier to get out of jail than in surrounding Bay Area counties.

Today, amid a national movement to eliminate bail spurred by concerns over the system’s inequality, Newsom argues that a person’s freedom shouldn’t depend on their ATM balance.

“Shamefully, California continues to use a cash bail system. The only two countries that even allow for-profit bail operations are the United States and dictator Duterte’s Philippines,” he wrote in an opinion piece last year.

▪  Immigration: The city under Newsom sponsored a campaign advertising itself as a sanctuary for unauthorized immigrants. But late in his tenure as mayor, Newsom also pushed a policy to weaken the city’s two-decade-old “sanctuary city” ordinance protecting immigrants in response to a major crime.

Newsom’s approach required the city to contact federal immigration authorities when they arrested on felony charges a minor suspected of being in the U.S. illegally. More than 100 unauthorized minors were turned over.

But the board stepped in, arguing Newsom went too far, and overturned his position so that it applied only to those with felony convictions. Supervisor David Campos said at the time that the vote “sends the message that we in San Francisco still believe in the Constitution and the basic principle of due process, that in this country you’re innocent until proven guilty.”

Now that he’s running for governor, Newsom emphasizes that he’s been called the “poster child for sanctuary policy,” delighting in a designation that made him a scourge of Fox News.

▪  High-speed rail: Newsom was an early backer of Brown’s high-speed rail project, but he soured on its prospects when the route and business plan changed. While promoting his book “Citizenville,” Newsom told the conservative Ben Shapiro Show in 2014 that he “would take the dollars and redirect it to other, more pressing infrastructure needs.”

“I am not the only Democrat that feels this way. I got to tell you, I am one of the few that just said it publicly,” Newsom added. “Most are now saying it privately.”

Newsom now says he would work to identify private investors for the rail project, a position that brings him back in line with California’s Democratic establishment.

▪  Health care: Tom Ammiano, a former liberal supervisor who ran against Newsom for mayor, sponsored legislation in 2005 requiring businesses with 20 or more workers to pay for health care insurance. Newsom initially voiced concerns that it could “have a serious impact on San Francisco’s (economic) recovery and our ability to compete.”

Newsom, stressing that he remained open-minded about expanding health care access to the uninsured, reiterated his concerns in a letter to supervisors that stated it could hurt small businesses and nonprofits. He instead wanted supervisors to call for an economic analysis of the proposal, and for them to convene a diverse group to study how to achieve the goals of expanded health coverage.

Newsom and his supporters today point to his work in helping create Healthy San Francisco by reaching consensus through a coalition that included business interests.

Ammiano ultimately backed Newsom’s compromise initiative, saying in the Chronicle it would cover more San Franciscans than his legislation because unlike his, which targeted uninsured workers, Newsom’s would cover anyone without health insurance – working, self-employed or the unemployed.

Still, Newsom’s early fretting about the economic impact is more in line today with the views of his opponents in the governor’s race, positions he’s cast as demonstrating a lack of leadership. Newsom is the highest-profile Democrat calling on the Legislature to advance a single-payer health care bill that does not specify how the state would pay for it.

Ammiano said it took Newsom a while to come around on other issues, as well, including municipal ID cards for unauthorized immigrants and legal marijuana. “He’s always been a Johnny-come-lately, in my mind, on many progressive issues,” Ammiano said.

Yet former Supervisor Chris Daly, another liberal Newsom detractor, said the then-mayor was better at owning the final product once he was convinced.

“Don’t hate the player,” he said of Newsom. “Hate the game.”

Christopher Cadelago: 916-326-5538, @ccadelago

This story was originally published February 23, 2018 12:01 AM.