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School District Leaders Earn Top Pay

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Teachers and others in the school community are complaining that Oakland Unified School District Superintendent Antwan Wilson’s administration is top-heavy with highly paid new administrators who had worked in Denver, CO public schools.

<p>Wilson, formerly an assistant superintendent of Denver schools, earns $280,000 a year plus benefits. In addition, he received a $28,000 moving allowance and an additional payment for six months of temporary housing while he looks for a new home, as well as reimbursement for his legal expenses for negotiating his contract with the district.

The price of benefits generally adds more than one-third to the cost of an employee’s’ annual salary.

Troy Flint, the school district’s spokesman, told the Post that he is working on gathering the information on the amounts Supt. Wilson is being paid for temporary housing and for his legal expenses.

Administrative salaries frequently become a major issue during contract negotiations between school districts and teachers’ unions, especially in Oakland where teacher pay is the lowest in the Bay Area.

 

Oakland’s two previous top executives were Gary Yee, acting superintendent who earned $250,000 a year; and Tony Smith, who was formerly a superintendent in Emeryville, earned $265,000 a year when he left the district.

 

Also from Denver, Chief of Schools Allen Smith earns $175,000 and received $15,000 for moving expenses.

 

Yana Smith, Chief of Organizational Effectiveness & Culture, Allen Smith’s wife, is earning $155,000 and $12,500 for moving costs.

 

Devin Dillon, Chief Academic Officer, Office of the Superintendent, is earning $175,000 plus $11,000 for moving.

 

Bernard McCune, Deputy Chief of the Office of Post-Secondary Readiness, earns $157,000 a year plus $17,000 for moving costs.

 

Ray Mondragon, deputy chief academic of early childhood learning, is earning $157,000. The position is grant funded.

A number of these positions are newly created and supplement existing top administrators in the district.

 

Other new officials include Isaac Kos-Read, chief of Communications and Public Affairs, who earns $192,000. He previously worked as director of External affairs at the Port of Oakland and was a public affairs consultant for the Oakland Metropolitan Chamber of Commerce.

His position is paid by the Oakland Public Education Fund, which has an office in the school district headquarters.

According to Flint, the district’s spokesman, Kos-Read plays a crucial role at the school district.

“Isaac brings substantial experience and expertise in Public Affairs and Communications, areas where the District has suffered from lack of capacity for years,” he said. “The marginal benefits of adding someone of Isaac’s talents yields benefits far beyond the cost in terms of increased ability to interact with diverse stakeholder groups, identify community concerns, and deal with those issues effectively.”

The Oakland Post is hearing from community members and district staff that they are concerned that the superintendent’s reliance on administrators from outside Oakland contributes to what they say is his team’s relative isolation from the concerns of local people and a tendency to make mistakes in judgment based on ignorance or disregard for local realities.

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At the event, 16 entities signed the EIP pledge, vowing to take steps to increase public contracting opportunities in their spheres for small and historically underutilized businesses.  The pledge signees included Hub International, the Port of San Francisco, the San Francisco Public Utilities Commission, California High-Speed Rail Authority, the Port of Oakland, Robert Graham of Webcor Builders, Holder Construction, the Weitz Company, Sky Blue Builders, Hornblower, Swinerton, Luster National, Talson Solutions, Center for Community Wealth Building, and the Construction Contractors Alliance.

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Toks Omishakin, secretary of the California State Transportation Agency, was one of the speakers at the event. Photo by Shellee Fisher Photography and Design.
Toks Omishakin, secretary of the California State Transportation Agency, was one of the speakers at the event. Photo by Shellee Fisher Photography and Design.

By Calvin Naito, Special to The Post

On June 4, a national nonprofit named the Equity in Infrastructure Project (EIP) – which aims to increase public construction contracting opportunities for small and historically underutilized businesses – held a day-long event in downtown San Francisco to rally supporters and build momentum to its cause.

It was attended by more than 100 individuals from public agencies, private firms, and other organizations committed to increasing contracting opportunities with governmental agencies, thereby creating more competition and lowering public costs.

The EIP event was held the Hyatt Regency San Francisco in conjunction with BuildIT, which aims to increase contracting opportunities for LGBT-owned businesses.

At the event, 16 entities signed the EIP pledge, vowing to take steps to increase public contracting opportunities in their spheres for small and historically underutilized businesses.

The pledge signees included Hub International, the Port of San Francisco, the San Francisco Public Utilities Commission, California High-Speed Rail Authority, the Port of Oakland, Robert Graham of Webcor Builders, Holder Construction, the Weitz Company, Sky Blue Builders, Hornblower, Swinerton, Luster National, Talson Solutions, Center for Community Wealth Building, and the Construction Contractors Alliance.

Following the workshop, BuildIT hosted a VIP evening reception honoring EIP, whose principals – Phil Washington, John Procari, and Rick Jacobs – accepted the award.

The event also set in motion the coalition’s efforts to implement recommendations from EIP’s “Procurement for Prosperity: A Playbook.”

The Playbook is a practical guide for public agency leaders and procurement and contracting practitioners to grow the capacity of small and first-time contractors, strengthen competition, and deliver better value for taxpayers.

Toks Omishakin, Secretary of the California State Transportation Agency (CalSTA), a long-time EIP supporter, also told attendees, “This is about commitment.  This has been a life’s work. This is a tailwind moment.”

The event’s presenting sponsor was Hub International, one of the largest insurance brokerages in the nation, which was joined by partners Travelers Insurance and the State Compensation Insurance Fund.

After the pledge-signing ceremony, attendees participated in a workshop in which they examined the policies, practices, and programs needed to meet EIP goals, learned from practitioners, and identified next steps toward utilizing the Playbook.

Ingrid Meriwether, formerly of Merriwether & Williams Insurance Services (MWIS) and current president of Hub International’s Aligned Risk Management, MWIS, described the hard-fought lessons she and her MWIS team have learned over the last three decades administering contractor development programs (CDPs) for the City and County of San Francisco, Alameda County, City of Los Angeles, LA Metro, and other municipalities.

The CDPs help small and local construction firms win public infrastructure contracts with these government agencies.  The program provides bonding assistance, contract financing, technical support, training, and other services to underrepresented businesses funded by public agencies who seek greater contracting participation with these firms.

Merriwether said programs like these “break down systemic barriers, create greater fairness, and save taxpayers money by enabling more competition.  The contractor development programs have, cumulatively, over two decades, helped contractors access over $1 billion in bonding, supporting over $380 million in awarded contracts, and maintaining a loss ratio 250 times lower than the industry average – while saving participating municipalities more than $27 million in contracting costs as a result of enabling more competition.”

Rick Jacobs, EIP co-founder and co-chair urged attendees make plans to meet again in the near future “to continue building on this work, share progress on organizational commitments, and discuss how we can collectively advance the goals of the EIP pledge.”

For more information on the EIP and to access a copy of the Playbook, go online to https://equityininfrastructure.org/

Calvin Naito is communications manager for Equity in Infrastructure Project.

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Oakland Post: Week of June 17 – 23, 2026

The printed Weekly Edition of the Oakland Post: Week of June 17 – 23, 2026

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Oakland Post: Week of June 10 – 16, 2026

The printed Weekly Edition of the Oakland Post: Week of June 10 – 16, 2026

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