The battle to become San Diego’s next city attorney is a story of stark contrasts. Assemblymember Brian Maienschein is a longtime politician who hasn’t practiced much law. Deputy City Attorney Heather Ferbert is a longtime municipal lawyer who has never before run for political office. Ferbert, who is endorsed by termed-out City Attorney Mara Elliott, says she will continue to lead the 170-lawyer office in much the same way Elliott has the last eight years. Maienschein says dramatic changes are needed on transparency, how property deals are negotiated and what he calls Elliott’s “chaos” leadership style that has featured dueling news conferences and criticism of other officials. While both candidates are Democrats, campaign mailers sent by Ferbert this week criticize Maienschein for being a Republican before switching parties in 2019, contending his “far-right Republican record” should disqualify him from the job. Mailers sent by Maienschein this week don’t mention Ferbert at all, instead focusing on policy proposals and Maienschein’s long list of high-profile endorsements — including from Planned Parenthood and the Sierra Club. Maienschein has been endorsed by most of the establishment — the county Democratic Party, most of the San Diego City Council and several members of the state Legislature. Ferbert hasn’t been endorsed by many local politicians. But she has been endorsed by the vast majority of local bar associations, which she says highlights that she’s more qualified for the job. While Maienschein has been a licensed attorney for 29 years, his license has been active for fewer than seven of those. He stopped practicing law when he began his political career, which included serving on the San Diego City Council before being elected to the state Assembly. Maienschein said his legal experience includes making laws on the council and in the Assembly, where he has served on the Judiciary Committee. He also stresses that he did practice law for a few years and teaches law at University of San Diego. “I’ve worked on the most complicated legal issues, not just that face the city, but that face the state of California,” he said in a phone interview this week. “The experience I bring is really broad and really deep and will benefit the city attorney’s office and the people of San Diego.” Ferbert strongly disagreed, contending his lack of recent experience practicing law could put the city in jeopardy financially and in other ways. “Are you going to choose the pilot who’s worked for the FAA making policy decisions the last 24 years, or the pilot who flew across the country yesterday?” she said in a separate phone interview. “It’s a no-brainer. The voters want a lawyer.” Ferbert listed specific ways Maienschein’s lack of experience could matter, including hiring people to lead the many divisions within the city attorney’s office. “Not being an experienced lawyer is going to make it really challenging to select the leadership you have around you and your ability to see through weak legal defenses or arguments and to give advice on the fly — and these are all things that we do,” said Ferbert. “How are you going to know if your managers are doing a good job or doing good legal work if you yourself don’t know how to do the legal work?” Maienschien countered that Ferbert has much more narrow experience. “If you look at my breadth of experience and what I would bring to the table, it’s so much broader than somebody who has practiced in such a tiny little area of municipal law,” he said. Ferbert helped write San Diego’s eviction moratorium and has overseen legal work related to funding for homeless shelters and the city’s transformation of the convention center into a shelter during the pandemic. Maienschein also noted that two former colleagues of Ferbert in the city attorney’s office who left for City Council seats — Marni von Wilpert and Raul Campillo — have endorsed him over Ferbert. “The people that have been in the office with her don’t support her,” Maienschein said. He’s also criticized Elliott’s leadership style, contending Ferbert would be four more years of the same. Maienschein said he would bring a more professional, subdued and non-confrontational approach to the job, criticizing Elliott for sparring publicly often with the mayor and council members. “I have always stood up to people when I’ve had to protect my district, but I think you can disagree without perpetuating what we see in politics today all the time, which is these Twitter wars,” he said. Ferbert agreed that dueling news conferences should be avoided and that personal criticism doesn’t make sense — but she said it’s not always that easy when things like generational land deals are on the table. “In a perfect world, some of these things might have gone differently and more smoothly,” she said of Elliott’s public battles with the mayor and council. Ideally, she said, council members and the mayor would take the city’s attorney’s advice behind closed doors and then adhere to it without a public squabble. “It is an elected city attorney position, and sometimes things don’t play out the way we’d like in a perfect world,” Ferbert said. Maienschein has tried to accuse Ferbert, who has handled some land deals for Elliott, of being partly responsible for the notorious 101 Ash St. deal and some other questionable land deals. He notes that an independent city audit criticizes the city attorney’s office for not giving the council and mayor proper legal advice and warnings about the risks of multiple real estate deals. Ferbert said every one of those deals took place long before she handled any real estate deals for the city. “I wasn’t involved in any of those,” she said. “It’s pretty ridiculous because I didn’t have anything to do with it.” Maienschein has also criticized the city attorney’s office for a string of losses and settlements in court in transparency and public records cases. “Over and over again, they are losing cases because they want to hide documents,” he said. “There doesn’t seem to be any learning that happens from these continued defeats.” Ferbert said Maienschein is wrongly blaming the decisions of city officials who withhold documents on the lawyers who have to defend them in court. “He’s oversimplifying, and he does not understand the role of the city attorney,” she said, endorsing Elliott’s repeated suggestion that a separate city department be created for records requests to boost quality. San Diego’s city attorney plays a key role in advising the mayor and council on land-use decisions, lawsuits and the legality of proposed policies. The job also includes overseeing misdemeanor prosecutions. Maienschein said it’s time for a change in the office. “I think I’m the right person at the right time for this job,” he said. “The city can stay with the status quo and continue to stumble along in a dysfunctional away, or they can have a city attorney that refuses to enter into these land deals and that changes policy to respect the rights of the public.” Ferbert said voters need to focus on who they can trust to be a good steward of taxpayer money. “Bottom line, the city attorney is about risk management and loss mitigation,” she said. “I think trust is really the key issue here. The differences between us is why the legal community has lined up behind me.” In the March primary, Ferbert got 53 percent of the vote, and Maienschein got 47 percent. According to the most recent campaign finance disclosures in late September, Maienschein had more cash on hand, $137,000 compared to $110,000 for Ferbert. Ferbert, 44, lives in Normal Heights with her husband and daughter. Ferbert grew up in Orange County and earned her bachelor’s degree from Long Beach State and law degree from the University of San Diego. Maienschein, 55, lives with his wife in Del Sur, which is just west of Rancho Bernardo. He has two daughters, a bachelor’s degree from UC Santa Barbara and a law degree from California Western School of Law.