Joe Eskenazi wanted a rare day off for Yom Kippur last month. He fasted and hoped to atone on the holiest day of the year, but then without public notice the San Francisco Board of Supervisors dropped a 56-page report depicting the not-so-holy history of nepotism and cronyism in the building department.

“It was a comptroller’s assessment of the Department of Building Inspection, which sounds as dry as you’d think, right? But there was stuff in there that was important,” said Eskenazi. “The thought of not doing that work was unconscionable.”

Eskenazi, 45, is the managing editor of Mission Local, a scrappy, hyperlocal and award-winning news site based in the Mission District, and has become one of San Francisco’s best-known muckrakers. His acerbic columns navigate arcane city bureaucracy, sussing out the truth and repeatedly taking city officials to task. There’s the corruption saga of former S.F. Public Works director Mohammed Nuru, the red-tape tribulations of a beloved San Francisco burrito franchise, and the eyebrow-raising role of ex-Mayor Willie Brown in a dispute over a residential deck.

On a recent Tuesday, Eskenazi met this reporter at a park in the Mission. Eskenazi, a baseball fan, wore a Giants cap and had a single sock imprinted with Albert Einstein’s face hiked over his pant leg after his bike ride. The previous day he’d filed a jaw-dropping story alleging that Angus McCarthy, the president of a key commission overseeing the Department of Building Inspection, had built his own residence, including a wine cellar, without the proper permitting. The story ricocheted through social media and up to the Board of Supervisors, who called for an investigation.

Eskenazi was busy that day dealing with the aftermath of the piece, and his mind often seemed elsewhere. But when speaking about working on Yom Kippur, his eyes swelled. “I thought I could do [the story] quickly, but I couldn’t. You can’t really atone in 15 minutes,” he said, adding, “I’ve come to think that Yom Kippur is an excellent holiday, and everyone should atone.”

Eskenazi is not a temple-going Jew, but his path to becoming a pillar of the local journalism community is intimately intertwined with the city’s Jewish landscape. As a young journalist, one of his first jobs was with the Jewish Bulletin of Northern California (J.’s predecessor), starting in 2000. He remained for nearly eight years, chronicling a burgeoning Jewish community transitioning into the internet age. His stories captured the heart-wrenching, the unseemly and the unusual in the Jewish world, from narratives of evicted rabbis to the stomach-churning story of one man’s attempt to sell a Nazi cross made of looted Jewish teeth on Craigslist. He said countless interviews with Holocaust survivors and veterans of Israeli wars were invaluable lessons in how to listen and document personal stories.

“He was probably one of the toughest reporters that we ever had,” said Marc Klein, J.’s editor and publisher during Eskenazi’s tenure. “He ran after stories more than most and loved a good investigation.”

Eskenazi’s penchant for holding gatekeepers’ feet to the fire — something that has helped earn him multiple awards, including journalist of the year from the Society of Professional Journalists of Northern California in 2019 — is apparent in his early reporting on the ethical and criminal wrongdoings of Rabbi Bentzion Pil, who was convicted of financial misconduct, and his attempts to push for more critical reporting of the Jewish Community Federation, a backbone of Jewish life in the city.

He graduated from UC Berkeley in 1998 and two years later started at the Jewish Bulletin. His memories of working there are often bittersweet. For years he stacked every edition of the newspaper at his desk, telling himself that once the tower of papers collapsed he would leave the job. “It did actually work out that way. The timing was eerily close.”

His stories captured the heart-wrenching, the unseemly and the unusual in the Jewish world.

While Eskenazi has moved on from his Jewish reporting days, issues of race and class are often at the forefront of what he covers in the Mission District, where gentrification and rising rents have displaced thousands of working class and Latino residents over the last decade. For Eskenazi, this came to a head with the repeated noisy protests of Manny’s, a Jewish-owned cafe and progressive cultural hub, which was deemed a “Zionist-gentrification” project by activists who called for the business to leave the neighborhood shortly after its November 2018 opening. The owner, Manny Yekutiel, had expressed his support for Israel’s right to exist, setting off the firestorm, which many in the Jewish community saw as antisemitic. In a 2019 column about the controversy, Eskenazi defended Yekutiel and criticized activists for “making a Jewish man’s position on Israel’s right to exist a litmus test for operating a business in the Mission.”

“When you are a Jewish journalist, and you write this story, you are not able to step back from it as someone who is not Jewish would,” said Eskenazi. “You’ve opened yourself up to personal criticism from all the bad faith people that were picketing Manny’s.”

While starting his muckraking career in Jewish news may have been out of necessity, Eskenazi does seem uniquely built for plumbing the depths of Bay Area intrigue as a local reporter. His father was a San Francisco workers’ compensation judge and his mother an artist and actor. He grew up in the East Bay and has spent his entire life around San Francisco — his first time leaving the country, in 2001, was to cover a Birthright trip to Israel.

In 2010, Eskenazi and his wife, Alexia Aubault, announced their marriage in J., stating that the pair — a journalist and a naval architect —  planned to “build a boat that can be sailed to a realm where print journalism is still viable.” They now live with their 6-year-old son and 3-year-old twin daughters in the Excelsior neighborhood. They have not yet built a boat nor found an answer to reviving print journalism.

Eskenazi’s career over the last couple of decades has paralleled San Francisco’s tumultuous local news upheavals. He spent years as a staff writer for the recently defunct SF Weekly, writing about one of the world’s rarest plants hidden in the Presidio and the inequality built into our food taxation system, and had stints at the long-struggling San Francisco Magazine. Now, as managing editor of Mission Local since 2018, he is running an online newsroom comprising four full-time staffers and a team of interns that seeks to fill local news gaps left by San Francisco’s contracting media industry.

Mission Local, started in 2008 by Lydia Chávez, a journalism professor at UC Berkeley, has come under criticism from activists who accuse the site of catering to gentrifying businesses. A 2010 article naming restaurants with rat infestations set a particularly bad tone with some. Eskenazi’s reporting, which repeatedly has taken aim at activists, especially the Calle 24 Latino Cultural District’s strong-armed attempts to fight gentrification, has rankled community members.

Multiple Mission District activists declined to speak for this story, but Supervisor Hillary Ronen, who represents the Mission, said the publication and Eskenazi’s “esoteric” writing, often sprinkled with obscure analogies, can feel estranged from the neighborhood. She said Eskenazi is “one of the city’s best reporters,” but also faults some of his earlier writing for not adequately hearing out concerns within the Latino community.

“They are fighting for the survival of their community,” Ronen said of local activist groups. “I’m not saying that it was always perfect. But, you know, also, give them a break.”

Before breaking his Yom Kippur fast with a quart of sugar-free Gatorade, Eskenazi was slogging through his story on the 56-page comptroller’s report. At 45, Eskenazi said, he is noticing new signs of aging. He gets dehydrated easily and feels fatigue and hunger come more quickly after contracting Covid-19 in January. “The report focused on so many problems that people have known about for so long, for decades,” he said. “To see it coming up again and again on the day I was supposed to be atoning for my own misbehaviors was profoundly dissatisfying.”