For almost six years, Gary Winuk was enforcement chief at the state's top political watchdog agency, the Fair Political Practices Commission.
Now he's representing Los Angeles County as it wages a high-stakes fight against an investigation by the FPPC over whether it illegally spent $1 million in taxpayer money on a political campaign.
The probe by state officials was launched after the Howard Jarvis Taxpayers Assn. complained about the county running glowing television spots and social media posts supporting Measure H, an effort backed by prominent businesses, labor groups and others to generate hundreds of millions of dollars a year for services dedicated to homeless people.
"Local governments are going to be incentivized to spend taxpayers' dollars on political advocacy unless they're stopped," said Jon Coupal, president of the Jarvis group. "This is one of the most egregious violations we've seen."
In a statement, L.A. County spokeswoman Lennie LaGuire said the county "strongly believes that it conducted this educational outreach appropriately," but declined to comment further.
The hiring of the firm that employs Winuk, who served as the FPPC's head of enforcement from 2009 to 2015, is an indication of how seriously the county is taking the matter, experts said.
Jessica Levinson, Loyola Law School professor and political ethics expert, said that by adding Winuk to the defense team the county is sending a strong message to FPPC investigators and attorneys who previously worked for him.
"One of the reasons is to scare off the other side. Another reason is because you want them to continue to take the case as far you need to go," Levinson said. "It's hard to think of somebody better qualified to take this case."
Winuk now works for the Kaufman Legal Group, which specializes in election law cases. On Monday, he and Kaufman founder Stephen Kaufman spoke to The Times outside of L.A. City Hall about the investigation. They insisted that the county's spending related to Measure H was legal, and Kaufman said they would be putting up a "vigorous defense." They declined to get into the specifics of the case.
Measure H, which needed at least two-thirds of voters' approval to become law, passed over a year ago with more than 69% of the vote. The tax is expected to generate $355 million annually that would be dedicated to services for homeless people.
The Howard Jarvis Taxpayers Assn. complaint contends that the county conducted an illegal political campaign by running ads with positive messages about the measure. Ads touted the measure as "real help" and "lasting change." They also featured inspiring music and mini-profiles of formerly homeless people, but stopped short of explicitly asking viewers to vote for the measure.
Anchored by a giant star-studded check mark, the final frames of the ads asked viewers: "Are you ready? Vote March 7."
Coupal's group argues that, while taxpayer funds can be used to educate the public with balanced information, they can't be used to run ads that promote a political measure. That would be "the force of government putting its thumb on the scale of an election issue," he said previously.
Lawyers working for the Howard Jarvis group mocked up ads in exactly the same format as those the county ran, and sent them to the FPPC for an opinion. The FPPC found that the ads would be considered political campaigning, according to correspondence from the watchdog agency.
Now, FPPC officials are having to deal with their former boss.
By the time Winuk left the organization in 2015, the FPPC had tripled the number of prosecutions it filed from 100 a year to 350, according to the agency's annual report for that year.
Winuk was also enforcement chief when the FPPC embarked on a complex investigation into whether Republican groups improperly funneled millions of dollars toward California ballot initiative campaigns in the 2012 election. The commission issued a record $16 million in fines in that case.