The Oaklandside is thrilled to announce the appointment of Esther Kaplan as its new deputy editor. This move represents a significant step forward for the newsroom as it aims to enhance its journalism and better serve the Oakland community. In addition to her role as deputy editor, Kaplan will spearhead journalist collaborations and investigations across the Cityside organization.
Bringing with her 18 years of editorial leadership experience from renowned news outlets, Kaplan most recently served as investigations editor at Business Insider. There, she led a team of eight journalists and played an integral role in producing award-winning investigations that garnered national attention. Prior to her time at Business Insider, Kaplan was the executive editor at Reveal from The Center for Investigative Reporting, overseeing a team that produced in-depth investigations for a national podcast. She also previously served as the editor-in-chief at Type Investigations, leading impactful investigative projects in partnership with diverse media platforms. Notably, she initiated the Ida B. Wells Fellowship to promote diversity within the field of investigative reporting.
What distinguishes Kaplan is her unwavering commitment to journalist development. Colleagues from her past roles have described her editing approach as “an act of love,” which combines top-notch editorial standards with a genuine investment in helping reporters flourish. Many journalists she has mentored have found their way to prestigious publications, including ProPublica, NBC News, The Los Angeles Times, The Guardian, and WNYC.
“Esther’s philosophy of leadership is exactly what we need,” said Tasneem Raja, editor-in-chief of The Oaklandside. “Her track record of nurturing talent while maintaining the highest editorial standards is already being felt in the newsroom.”
In her new position, Kaplan will oversee half of The Oaklandside’s reporting team and will serve as the second-in-command in the newsroom. Her considerable expertise in nonprofit journalism, particularly in securing sustainable funding for investigative projects, will also enhance the broader Cityside organization in her role as Cityside’s Newsroom Collaborations Editor.
As an Oakland resident with a child enrolled in Oakland public schools, Kaplan has expressed her commitment to understanding the city’s diverse communities and complex issues. “Oakland is a fascinating place with a rich history of cultural innovation and resistance,” Kaplan remarked. “At the same time, it is a city grappling with significant budget and governance crises. It will be an adventure to dig into accountability journalism alongside the Cityside and Oaklandside teams.”
Kaplan’s arrival comes at a pivotal moment for The Oaklandside, which continues to grow its coverage and influence. Each month, over 250,000 individuals engage with its reporting, contributing to the publication of more than 1,000 stories annually. The newsletter reaches nearly 30,000 subscribers, and close to 3,000 supporters provide financial backing as small-dollar donors or members. Recently, the newsroom welcomed public safety reporter Roselyn Romero and elevated Natalie Orenstein to senior reporter, focusing on housing and city hall issues.
In the past year, The Oaklandside has made headlines by uncovering elevated lead levels in the water fountains of Oakland’s public schools, investigating corruption allegations surrounding recalled mayor Sheng Thao, and revealing the deterioration of one of Oakland’s previously esteemed homeless shelters.
“We’ve been intentional in expanding our team thoughtfully,” Raja commented. “Esther’s blend of editorial and investigative expertise, leadership background, and commitment to Oakland makes her an ideal fit as we celebrate the remarkable growth and impact of our first five years and plan for what lies ahead in the next five years.”
This is indeed an exciting period for journalism in Oakland, with much more to anticipate. The Oaklandside invites feedback and encourages the community to reach out via [email protected].
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