In an ironic twist of fate, the biggest threat to Judge Diane Ritchie’s re-election bid could be her own rap sheet. Since winning a seat on the Santa Clara County Superior Court bench in 2008, tales of Ritchie’s disjointed processing of cases and casual interactions in court have become legend.

There’s that one time Ritchie gushed over how “wonderful” it was to see a defendant she’d once represented, back when she was a private attorney, before asking him for his phone number and inviting him into her private chambers to chitchat. Then there’s the time Ritchie, currently handling civil cases, had a landlord act as an interpreter for the plaintiff, who happened to be his disgruntled tenant. And then there was the time she let a case proceed against a fellow judge, in which a litigious woman requesting a restraining order against him testified that President Obama, the First Lady, Justin Bieber and Beyonce were stalking her and part of the same conspiracy.

Ritchie’s actions have never broken the law or resulted in a formal reprimand, but they have led to her temperament—and judgment—to come into question. No incumbent judge in the county has been challenged for re-election in the last 16 years, until now, as Ritchie fends off two campaign opponents and what appear to be critics on all sides.

The Mercury News, in particular, has pilloried Ritchie to the point that it has published a dozen articles about her indiscretions since February. By comparison, the newspaper has published 15 stories related to the San Jose mayor’s race in the same timeframe.

“Yes, I did ask for his phone number,” Ritchie says sheepishly, in a recent interview with San Jose Inside, regarding one of the aforementioned indiscretions. “Yes, I did have him come talk to me in my chambers. I think that I—probably, it doesn’t look good. So I did think about that.”

Perhaps one of the most awkward decisions in Judge Ritchie’s tenure, according to attorneys who have been in her courtroom, occurred when her husband sat in the witness stand while she handled misdemeanor cases.

It’s relatively common for schoolchildren to take field trips to courtrooms and sit in the jury box, but no one reached for this story knew of an occasion when a spouse rode shotgun on the bench.

“I have never seen anything like it before or since,” a local attorney tells San Jose Inside, adding that Ritchie introduced her husband as being there for “moral support.”

Ritchie denies such an incident occurred in an interview but later hedges when asked for a flat-out denial. “He sat in the courtroom,” she says, noting her husband visited court four or five times. “He sat where everyone sits. I think he sat in the front row. Well, he definitely sat in the front row.”

Asked again if it happened, she demurs: “I can’t picture that.”

A civil attorney for two-plus decades who also worked in the District Attorney’s office for four years, Ritchie defeated two DA hotshots—Jay Boyarsky and Lane Liroff—in the 2008 primary, as well as Jesus Valencia, who was later appointed a judge. She bested Liroff in the November runoff. Until that point, she was relatively unknown.

“I won because I was the best qualified candidate—and I’m a woman,” Ritchie says, disputing the notion that she won a down-ballot race, in which voters are unfamiliar with most candidates, specifically because of her gender. The victory, however, later became referred to as “The Ritchie Effect” in DA circles.

Citing multi-million dollar civil claims she won against fast-food giants, as well as a sexual orientation discrimination lawsuit against Morgan Hill’s school district, Ritchie believes she’s now the victim of overcoming the odds—at the expense of a couple prosecutors and a newspaper that saw its endorsement fall flat. Six years later, she suspects there is a coordinated effort to assassinate her character.

“They do take it very personally,” Ritchie says.

Judge or Be Judged

Almost universally appreciated as a pleasant woman, Ritchie has made a concerted effort to be the anti-Judge Judy. She refuses to belittle defendants and attorneys, and whispers when making cringing admissions. There is vulnerability when her upper lip quivers in private conversation.

Handling low-level misdemeanors when she first took the bench, Ritchie now oversees civil cases that can range from small claims to living trust disputes. Her overriding goal throughout, she says, has been to get it right and treat all parties with respect. At times, that has led to taking advice from fellow judges on down to court clerks.

“I was ready when I first came in, but if you look at any new judge, they’re learning the craft,” Ritchie says. “It’s a super-hard job for everyone.”

That job has only become even more difficult since the campaign and ensuing media blitz. Both plaintiffs and defendants are each entitled one chance to challenge a judge’s ability to hear a case in civil court, and Ritchie admits that attorneys—some at the behest of their clients—are now challenging her ability to hear cases almost “half the time.”

“I had a good reputation,” she says, noting that the number of challenges should drop once re-elected. “Nobody wants to have their case in the newspaper, and I don’t blame them.”

But Ritchie’s political opponents see the increase in challenges as a referendum.

“That’s pretty amazing,” says Matt Harris, a 23-year veteran of the District Attorney’s office who is hoping to unseat Ritchie. Having overseen everything from low-level misdemeanors and homicide cases to white-collar crime, Harris has also spent time in the U.S. Attorney’s office. With credentials similar to Ritchie’s past opponents, Harris has gobbled up the bulk of local law enforcement, elected official and judge endorsements in the race.

“It’s the kind of experience you can’t buy,” he says. “You got to live through it to get it.

“When I saw everything that was going on, I decided there was a need for someone who had experience and would run the court in the manner in which it should be run, that gave everyone a fair and impartial hearing in a way that the judge does not become part of the case.”

Annrae Angel, a criminal defense attorney for 21 years in Santa Clara County, also decided to oppose Ritchie after hearing concerns about the judge in the jurist community.

“She’s a very nice woman,” Angel says. “This is not about who she is. This is not about if she’s nice or not. I just think Santa Clara County deserves to have judges who are fully aware of the courtroom, participants and the law.”

Angel’s experience offers a decidedly different perspective from most of the 70-plus judges currently on the county bench, as she’s stood all of her career on the opposite side of the aisle from prosecutors.

“It’s important to have both perspectives on the bench, and in Santa Clara County we are lacking a criminal defense perspective,” Angel says.

Ritchie argues that she has that perspective—in addition to being a “tough” judge—as part of the criticism of her first term stems from a willingness to empathize with defendants.

“Just look at where we (are) in a courtroom, sitting above people,” Ritchie says. “We’ve got the robe, we’re the face of justice and we can’t afford to ever have it be about us. I think for me it’s important to make people know that I don’t look down on them.

“Here’s the thing—you can either be a pushover or a tiger lady, and I try to walk through the middle. I want to give everyone their due.”