City Administrator Jestin Johnson has resigned, Mayor Barbara Lee announced Sunday morning.
Assistant City Administrator Betsy Lake will temporarily take over the role.
Text messages reviewed by The Oaklandside, which were released on the city’s public records portal last week, reveal that Johnson and his high-ranking lieutenant Harold Duffey discussed female employees and colleagues in crass and inappropriate terms in recent years.
“On Friday evening, I learned about certain degrading and unprofessional communications involving Mr. Johnson,” Lee said in a statement Sunday. “We promptly conducted our own investigation and verified these communications, which are wholly incompatible with the values of this administration and those of the people of Oakland. Under my watch, I will not tolerate transgressions of this nature.”
Johnson, who was hired in May 2023 by then-Mayor Sheng Thao, did not immediately respond to an interview request.
Johnson and Duffey described their reaction to women’s bodies on more than one occasion, and called a high-up female colleague “emotional,” during exchanges in 2024, the text messages show.
In the spring of 2024, Duffey texted his boss that a high-ranking female city official was “tough.”
“Got the old player mesmerized,” he wrote.
“I’m telling you, you have to sit next to her,” Johnson responded, about his employee. “I have to force myself to only look in her eyes. She had me a little giddy yesterday when we had to take pics.”
Former city official Harold Duffey, shown at a press conference in 2022, engaged in inappropriate texting with Jestin Johnson. Credit: Amir Aziz/The Oaklandside
On another occasion, Johnson texted Duffey that another female staffer was his “kryptonite.”
“My goodness, [she] has a helluva walk,” he wrote.
The Oaklandside reached both women, who declined to comment for this story. Duffey did not immediately respond to an interview request.
As city administrator, Johnson was second only to the mayor. He oversaw the operations of the entire administration. He was appointed by Thao in 2023 and kept on by Lee.
Duffey worked for Oakland for four years, leading the Public Works Department, then overseeing a number of operations as an assistant city administrator in Johnson’s office. He left the city late last year to become the city manager of Brentwood. The texts appear to span a period when Duffey held different roles in the city.
Also in the spring of 2024, Johnson and Duffey trafficked in stereotypes as they texted about making inroads with a former city official. The Oaklandside has retained the messagesʻunconventional punctuation.
“He’s the one that I believe can be a great asset for us both as we start turning the ship,” Johnson wrote. He added that another female high-ranking city official, LaTonda Simmons, “may be in his ear.”
“Of course she is but he is very sophisticated brother…other word that shit ain’t stinking,” Duffey responded. “You think a black man – I mean a black man, highly educated and very successful- would fall for LaTonda’s Game. She is becoming more emotional and he deals with facts.”
Simmons worked in various positions for the city of Oakland for 23 years, and was mostly recently an assistant city administrator — the same position as Duffey — until Johnson fired her in 2025.
On Sunday evening, Simmons issued a statement calling the “swift action” of Johnson’s resignation “critical to mitigate further damage to the women of Oakland.”
“Reducing women to sexualized functions and labeling women as emotional undermines and delegitimizes their value. Given his references to me and what his text shows, it comes as no surprise. I reported to then-Interim Mayor, now City Council President, Kevin Jenkins, and others that Jestin was disparaging me and interfering with my work, but I received no support,” Simmons said in the statement, issued by consultant Candace Reese Walters on her behalf.
We reached Jenkins by phone right after the statement came out.
Asked about the “disparaging” comments by Johnson that Simmons alleges she reported to him, Jenkins, reviewing the statement for the first time, said, “I have no idea,” and declined to comment further.
Simmons’ spokesperson, Reece Walters, was herself an alleged victim of sexual harassment and discrimination by high-ranking Oakland officials. Reece Walters worked as the Department of Violence Prevention’s public information officer. She alleged that in 2022 her boss, Chief of Violence Prevention Guillermo Cespedes, routinely made “offensive and inappropriate comments” about her, that she was paid less than male colleagues with similar jobs, and that she was fired for submitting whistleblower complaints.
The City Council approved a $1 million settlement last year to resolve a lawsuit Reece Walters filed against Oakland. Cespedes’ attorney told The Oaklandside at the time that Cespedes denied all allegations of wrongdoing and that the city had investigated and cleared him.
Johnson’s resignation comes just a couple days after Oakland officials unveiled Lee’s proposed budget adjustments for the coming fiscal year. Oakland has been grappling with deficits for several years, and city leaders, including Lee, have staked Oakland’s finances on passage of a contentious ballot measure that would impose a new parcel tax on residents.
“I want to reassure Oakland residents that government services and operations will not be affected during this time of transition. I was elected to represent the values of the Oakland community and that work and commitment continues,” Lee said in her statement.
This is a developing story. Check back for updates.
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