In December, Oakland announced the hiring of Dr. Jason Lester to lead the Human Services Department, which oversees homelessness services and programs for seniors, disabled residents, and children. In a press release citing his extensive career in social services, Mayor Barbara Lee said his “experience and dedication to Oakland values make him the perfect person for the role.” 

But after five months, the city terminated Lester’s employment. 

City Administrator Jestin Johnson confirmed Lester’s departure to The Oaklandside last Wednesday. Johnson thanked Lester for his service and wished him well in his next endeavor. 

“Effective immediately, Lea Lakes will serve as Interim Director as we work on a nationwide search for the next permanent director,” Johnson said in a statement. Lakes was hired last October and previously served as the deputy director of Human Services. 

“My senior leadership team and I are working closely with the department and our partners to support [Human Services] and ensure continuity in our work,” Johnson added.  

Lester, who moved to Oakland from Colorado, said his termination came as a shock. In an interview with The Oaklandside, he said the city had given him $10,000 to relocate, and he had been planning to move his family here.

“I’m a 43-year-old man who has had an extensive career,” Lester said. “I can’t believe I would be fired from this role.” 

According to Lester, Johnson told him that the city wanted to take the department in another direction. 

In an email, city spokesperson Karen Boyd said it’s the city’s practice not to comment on personnel matters.

Lester has his own theory about his firing. 

During his short time in Oakland, Lester said he repeatedly butted heads with Assistant City Administrator Michelle Phillips about department operations. He believes he was pushed out after these conflicts with Phillips, whose job includes providing support to Human Services. He said Phillips wanted to remove him to give the director’s job to Lea Lakes, who previously worked with her in the city of Minneapolis.

“I think this was the whole plan, and I don’t think she expected me to come in pushing back on many things,” Lester said. 

Johnson and Phillips denied this in an interview, with Johnson noting that if this were their intention, the city wouldn’t have gone through a full recruitment process for the director role. He added that Lakes didn’t apply for the director role and that the city has an outside firm handling the recruitment process for the next permanent director. 

“With respect to ACA Phillips wanting that job to go to [Lakes], that is certainly not true,” Johnson said. 

Boyd said Phillips oversees Human Services as part of her management portfolio. For the past few months, Phillips has provided support and guidance to the department’s managers — Lester and Lakes — as they were onboarded and transitioned into their roles. 

“This guidance was intended to ensure they were well versed in city policies, procedures, and practices, as well as management expectations,” Boyd said in an email.  

Phillips said she maintained a direct line of communication with Lester during his tenure. Noting that the department lacked permanent leadership for a long time, and that Lester was coming to Oakland from a different state, she said she wanted to ensure Lester had the tools he needed for the job. 

“The way I saw it was I was making myself available and coaching new leadership to be successful,” Phillips said. 

A series of disagreements preceded Lester’s firing

One of Lester’s big concerns was Lakes’ role. According to Lester, Phillips asked him to ask Lakes to lead Head Start, the childcare and early childhood education programs overseen by Human Services. Lester said that when he asked about whether Lakes had completed a background check, Phillips appeared upset.

Phillips said she had a conversation with Lester about the Head Start role after the former director resigned. But she maintains that she never told Lester to appoint Lakes to the role. 

The city has since appointed an interim manager with all the required training, Live Scan clearance, and Head Start experience, according to spokesperson Karen Boyd. City officials declined to share the name of this person, saying that they haven’t been announced yet to staff.

According to Lester, he also had a disagreement with Phillips over the reopening of the West Oakland Senior Center, which has been closed for roughly two years for renovations. Lester said he proposed a soft reopening of the center on March 30, but Phillips wanted to postpone the opening to April 22 so Mayor Barbara Lee and Councilmember Carroll Fife could attend the ceremony. 

“Pretty much everything I did, there was serious pushback,” Lester said. 

Phillips and Johnson said the delayed opening had nothing to do with making sure elected officials could attend. According to Johnson, the center isn’t ready to open; he noted that there was a break-in two months ago, and that they still need to furnish it and figure out staffing. 

Phillips said several seniors who did a walk-through of the center had been unhappy about the incomplete conditions. She said Lester told her at a meeting that he planned to reopen the center, and she asked him to delay it to address these issues. 

According to Lester, Phillips opposed his meeting with representatives from SEIU Local 1021, who represent some Human Services workers. He said the union had grievances about workers not getting breaks, not receiving hands-on supervision, and being mistreated. 

“I got the information from the union and center directors, but [Phillips] twisted it to make it about my lack of leadership,” Lester said. 

Johnson said all department directors are instructed to make sure they have representation from the city’s employee relations team when they meet with the unions. Phillips said she repeated this directive to Lester after she learned he had met with the union without a representative. 

“I never told him he couldn’t meet with them,” Phillips said.

Human Services has had a rocky couple of years

In 2023, then-Mayor Sheng Thao’s proposed budget called for merging Human Services with the Parks, Recreation, and Youth Development Department, while removing homeless services to a different department. That didn’t come to pass, but the proposal coincided with the beginning of a chaotic period for the department. 

Last summer, the city placed Diveena Cooppan, the director of the Head Start program, on administrative leave, along with another employee. City officials didn’t share why. This deeply concerned advocates of the program, who at the time were worried about the Trump administration targeting funding for Head Start programs around the country. Lester said Cooppan was brought back but retired this year. 

According to public records, four city employees involved in Human Services filed legal claims against Oakland last year. Several made allegations that they faced discrimination and harassment. 

Meanwhile, the department has struggled to recruit. According to the city’s most recent staffing report, Human Services has a vacancy rate of 28.52%, which is one of the highest for large departments. 

Johnson told The Oaklandside that all of the division leaders at Human Services “are very good at what they do” and that the city is in the process of finding a new head of the department. 

“We’re going through the recruitment and hiring process, making sure whoever we bring on board is the right fit for the organization,” Johnson said.  

Lester said he enjoyed working with many people in the city, but that Human Services needs more support. As an example, he said he had effectively no onboarding, and only received the ability to approve time sheets a few weeks ago. 

Another challenge when he started the job was discovering that Human Services had roughly $7.4 million in unpaid invoices stretching back multiple years. He said money was owed to local community partners, including Brighter Beginnings, Abode, Family Support Services, Roots Community, and the East Oakland Community Project. 

Boyd, the city spokesperson, said it’s unclear where Lester got the $7.4 million figure. She said it’s true that prior to his arrival, there was a backlog of contracts and purchase orders that staff had been working to resolve. 

“Staff confirmed that as of (April 3), there are currently no outstanding finalized contracts or pending purchase orders in the queue,” Boyd said. “This is largely due to interdepartmental coordination with the Finance Department and commitment of the Department of Human Services staff.” 

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