Key City Departures as Lee is Poised to Assume Mayor’s Seat
Three high level administrators are in the process of leaving City of Oakland employment as Oakland’s new Mayor Barbara Lee prepares to take office. Finance Director Erin Roseman is resigning, effective mid-June; and Head Start Director Diveena Cooppan, and Assistant Director Martina Bouey are in the process of being terminated by the City Administrator’s Office [CAO]. Roseman tendered her resignation in mid-April. Cooppan and Bouey were apparently put on leave late last Month, with separation planned Friday May 2nd.
Head Start Administrators Fired During Turbulent Time for Head Start
Cooppan and Bouey’s roles at Head Start may still be in flux. Unlike other city directors, additional federal rules require an advisory board hearing and a Council deliberation before termination of Head Start administrators. In what appeared to be a sudden decision to terminate the two, the CAO took no such steps. According to an email sent by the CAO to Human Service's staff last week viewed by this publication, Cooppan was put on leave on April 25 with a termination date of May 2. At a meeting of the Head Start program's oversight bodies Friday, Cooppan's assistant, Clara Sanchez, said Cooppan learned about her termination the day she was put on leave and had not been approached about any disciplinary matters before hand. It’s unclear if the City Administrator’s office was aware of the additional steps required to fire Cooppan.
The dismissals happen as the entire Western region faces the Trump administration’s inexplicable attempts to weaken the program. In early April, Trump’s administration shut down the Region 9 Head Start office, which oversees Oakland’s Head Start program, as well as programs in other parts of California, Nevada, Arizona, Hawaii and some US Territories.
The uncertainty created by the dismissals in light of the attacks from Trump led to a rancorous and pointed joint meeting Friday of the advisory organizations that oversee Oakland’s Head Start program: the Head Start Advisory Board, the body federally tasked with oversight of the program; and a local-originated body, the Parent Policy Council. The meetings ended with a promise by Council Member and Life Enrichment Committee Chair Carroll Fife, who was present at the meeting, to agendize Head Start’s issues and the dismissals to the Life Enrichment Committee as soon as possible.
Controversial Period for Cooppan
Cooppan’s run at Head Start has coincided with a tumultuous period for the program. In 2021, when the Life Enrichment Committee’s Head Start liaison role was filled by then-Chair Loren Taylor, Coopan and Taylor signed off on the closure of three Head Start sites—two in East Oakland and one in Chinatown. The programs had been found deficient in federal Head Start certification metrics and lost their federal funding. Legislation from Carroll Fife, Rebecca Kaplan, Nikki Fortunato Bas and Sheng Thao on Council restored the program sites, but only through city funding from the General Purpose Fund—those sites didn’t regain their federal funding.
Public Sentiment on Cooppan and Bouey Split
Head Start advocates, workers, and parents appear split on the legacy of the Oakland Head Start Administration. Some measure of support for Cooppan and Bouey was visible at the meeting among members of the Advisory Board and parents and advocates. Head Start Advisory Board Chair Niya Scott-Smith expressed solidarity with Cooppan and concern about the process.
“Now, I am upset about the possibly illegal termination of our director, Miss Cooppan…what that signifies is an ongoing and egregious disrespect of the leadership of our Head Start program,” Scott-Smith said.
Dr. Ida Oberman of Faith and Action East Bay, among others, called in to the meeting to criticize the move to fire the administrators, especially during a period of instability created by Trump.
“Oakland Head Start is a city commitment and a city program, it is our commitment to do all to persevere and support in these difficult times...the leadership that was let go on Friday should be restored so that there is guidance… a commitment should be made to make no further cuts in the leadership or staff,” Oberman said.
But there also appears to be significant and long-standing opposition to Coopan’s policies and performance by others.
Clarissa Doutherd, the Director of Parent Voices, voiced support for the termination of the two administrators at Friday's meeting. Parent Voices is an advocacy organization that was a significant driver in the effort to reopen the three Head Start sites several years ago and is a plaintiff in an ACLU suit against Trump’s Head Start attacks. Doutherd pointedly said any focus on rehiring the administrators was misguided.
“[these] administrative positions were unable to show real commitment to equity. We saw instability in hiring practices and inability to follow administrative protocol and deliver programs like a full apprenticeship program, expanding the workforce and keeping the East Oakland sites fully staffed...[Coopan was] unable to deliver unspent dollars into programming, into community. Look, I understand this is complicated, but we must be diligent and hold administrators accountable when they do not perform,” Doutherd said.
Parent Voices opposition to Cooppan has been publicly evident for months, since a City Council meeting last October where Parent Voices members blamed Cooppan directly for the program’s serious under-enrollment issues and being unable or unwilling to capture Measure AA and Measure C dollars which ostensibly have Head Start applications. On the dais, Doutherd accused Coppan of “lying” about the funding and of harassing and retaliating against East Oakland staff Head Start staffers.
“This is retaliation against black folks, that’s how we are perceiving this. Those sites have one director, one teacher, and sometimes have to close because there's no staff,” Doutherd said.
Several other Parent Voices members at that meeting accused Cooppan’s department specifically of retaliating and marginalizing Black staff at the sites.
“A majority of the staff were African American, most of the long, long term employees. Now it's hard to find African American teachers within Head Start,” Taisha, another Parent Voices member, told Council.
Cooppan told Council members at the same meeting that the three Head Start sites that CMs had moved to refund in 2019 were severely under-enrolled: Arroyo Viejo’s site had only four slots of 12 filled; and Tassafaronga, in deeper East Oakland had only six slots of 24 filled at that time. Nevertheless, Franklin, though seriously under-enrolled in Chinatown, had the best ratio, with 10 of 16 slots full.
At the October meeting, Cooppan admitted there was ”a significant under enrollment problem”.
“We have sufficient families on the waitlist. And the primary reason [they are not being accepted] is that we do not have staff,” Cooppan said.
Cooppan said there is a national staffing crisis in which Oakland competes poorly for trained staff against other jurisdictions. Cooppan did not elaborate on the delay in leveraging other funds, but did say that some funding is based on enrollment, a catch-22 due to being unable to hire enough teachers. Cooppan and Assistant City Administrator Latonda Simmons promised to return to Council with reports on the hiring issues, under-enrollment and funding—but the issues did not return to Council before the moves to terminate Cooppan and Buoey in late April.
Head Start worker’s Labor Union, SEIU 1021, Also Critical of Administrators
At last Thursday’s meeting, Parent Voices was joined by SEIU 1021 organizer Rafael Botello, representing Head Start workers who were also, he said, dissatisfied with the administrator’s performance
“A lot of our staff have felt kind of thrown around by the leadership of this program for a long time, and they’re concerned that those that actually work and run the program haven't been met with. We also have a lot of frustrations with how our staff have been treated in this program…a lot of times, you know, our staff concerns aren't listened to by upper management,” Botello said.
Botello also touched on the troubling reality that the CAO did not appear to have a continuation plan after firing the two Head Start administrators—a unifying worry for those on both sides of the termination issue.
At the meeting, Carroll Fife, who was in attendance, agreed that there are questions about the proper steps to dismiss administrators and the lack of forward planning. Fife agreed to agendize the issues at a Life Enrichment Committee meeting later this month.
Roseman Prepares to Leave After Year of Public Visibility on Oakland Budget Issues
Meanwhile, Erin Roseman will leave the Finance Department after five years as its Director. Though resigning, Roseman's last year of tenure has been under a cloud of opposition that’s most recently come to an unusually explicit public head at City Council and Committee meetings. In a power vacuum left by the departure of Mayor Thao, Roseman’s influence has been said by her detractors to have increased, but with poor results.
Roseman has been associated with several controversial moves over the past year:
—a supposedly erroneously published quarterly finance assessment that falsely claimed Oakland was at the precipice of insolvency;
—declining to sell Measure U bonds, a decision supported by the CAO with perilous potentials for infrastructure and housing projects
— a controversial parsing of the usage of a vehicular purchasing fund that has the City waiting to pay for three dozen police vehicles sitting at the dealership lot
Roseman presided over one of the most tumultuous budget processes in recent years from 2024 to 2025, as the City’s share of covid-era ARPA funding ran out and increasingly large gaps between revenue and expenditures became visible—especially in OPD spending. The OPD again brought the City to the edge of a fiscal cliff with unbudgeted spending in 2024, just as it had in 2020 before the arrival of ARPA money saved the City’s budget and obviated nascent significant cuts that had just begun with the aid announcement was made. The City and Council relaxed the spending cuts and even increased OPD spending.
The final outcome of Finance and City Administrator’s Office balancing processes undertaken in October 2024 won’t be known until late mid to late May, with Roseman’s last day in office in mid June. Although the administration of Interim Mayor Kevin Jenkins announced last week that it would be a few days late with presenting the budget, legally mandated to be presented on May 1, the delay likely has nothing to do with Roseman’s resignation. Roseman resigned in mid-April and will continue in the role for over a month to come.
City Moves to Settle Suit That Alleged Corrupt Election Processes
On Tuesday, the City Council will consider settling a suit brought by the Alameda County Taxpayers Association [ACTA], a conservative Alameda County organization and Marleen Sacks, a local conservative gadfly and pro-Israel activist. The suit is focused on an allegation that the City accepted the candidate documents for Sheng Thao and other Mayoral candidates after the 5pm deadline in 2022; the suit sought to invalidate the election among other efforts.
The City does not admit to culpability nor an invalid election process in the aftermath of a serious error by the Office of the Clerk in 2022. In the settlement, the City agrees to certain actions at the heart of the dispute and to pay $270K the petitioners attorney fees.
Grave Mistakes of 2022 Candidate Submittal Process Are Not Disputed
The grave mistakes in the process for candidate submittals to the City Clerk is public record and not disputed. Even local television news stations at the time reported the mistakes correctly. In the run to complete state and city mandated processes for elected office in 2022, the City Clerk’s office inadvertently gave candidates and the public erroneous information about the filing deadline to run for Oakland office. The Clerk told candidates they had until August 17 at 5pm to bring all of their paperwork to the office, which includes signed sponsorship sheets and other documents.
Based on this information, the Clerk further compounded the error by setting up appointments for candidates, including Thao, to turn in their paperwork all the way up to the erroneous date, which was three business days after the correct deadline. The mistake was not caught until the deadline day, Friday August 12 and the clerk called all the remaining candidates and told them they had until 5pm the same day to turn their paperwork in or miss the ballot. In the ensuing chaos at the office at City Hall, the City Clerk’s time stamp malfunctioned as well, giving incorrect time stamp receipts to all of the filings for the day.
In other fall out from the chaos, the Clerk also misinterpreted rules about candidate sponsorship, that, for a brief time, kept candidate Alyssa Victory off the ballot. Victory also sued and reached out to state authorities, and was successfully reinstated after that mistake was corrected. But Victory's situation is not part of the suit.
Sacks and ACTA, as well as other local center-right voices, seized on the errors in 2022 and 2023, arguing that the mistakes and other City policies invalidated the election and Thao’s term. But neither Sacks nor ACTA moved to sue to prevent the election from proceeding; the parties sued after the election outcome that gave Thao her narrow victory, something Judge Jenna Whitman noted in throwing out the portions of the suit requesting the election be invalidated.
The plaintiffs sued on a variety of issues:
—seeking direct accountability for one clerk specifically, Krystal Sams
—video evidence, which could have revealed the times of arrival of various candidates had been deleted by the time it was requested
—the suit sought the invalidation of the election over the alleged late filing by Thao and the fact that the ballot didn't allow enough rank choice voting options for all ten candidates
As part of the settlement, the City will pay the plaintiff’s lawyer’s fees, and commit to curing issues brought up in the suit. The City’s own mandates on City Hall video recordings require that they be stored for a year, but the City has destroyed its video recordings within weeks, instead of holding on to them for the mandated year as common practice. The City also had a malfunctioning time stamp for document receipt, which made it difficult to create a paper trail verifying when applicants actually handed in their paperwork—the City promises to make better efforts to keep it functioning correctly.
City Admits no Fault in Settlement
Though the City also commits to not accepting late paperwork, importantly the City doesn’t admit that it did receive paper work after 5pm. In documents rebutting Sacks’ arguments during the period that lawsuit was in process, the City directly responded that it believed that Thao and others filed their paperwork on time.
Judge Had Already Thrown Out Argument to Declare Election Invalid
In October 2023, the judge threw out the Sacks/ACTA quest to invalidate the election in one of the last decisions before the two parties agreed to a settlement; the judge also threw out the claims on ranked choice voting slots, noting that the City's Charter does not absolutely compel the City to have as many slots as candidates in the charter language.
Even if the allegations were true, the Judge noted, about the lateness and Sam’s actions, the Clerk’s alleged attempt to fix the mistake constituted a better outcome for the public than what was sought by Sacks/ACTA, the invalidation of the election:
“Although petitioners would have the court focus on Sams’ wrongful conduct, the court must read and consider the complaint as a whole, considering all of its parts in context. This includes the allegations that Sams’ office had advertised the wrong filing deadline, causing several candidates to schedule appointments after the actual filing deadline, and after realizing the mistake, Sams engaged in last-minute efforts (however misguided) to rectify this mistake.
In this context, Sam’s decision to accept tardy nomination paperwork, even if erroneous or deceptive, had the effect of restoring fundamental fairness to the nomination process by excusing a technical defect that was precipitated by the Clerk’s office. To be clear, the court does not sanction the unilateral and secretive manner in which this result was allegedly achieved; but that does not change the overall effect of Sams’ conduct, which was to expand rather than impair the fair expression of popular will.
By contrast, petitioners’ demand to disqualify otherwise diligent candidates from appearing on the ballot and conduct a new election would undermine, rather than ensure, fundamental fairness in election procedures, penalizing candidates who were misled by the Clerk’s Office, and would restrict rather than promote the fair expression of the popular will. Viewed through the lens of due process, petitioners’ remedy could be considered worse than the underlying error.”
City Administrator Will Propose Using Measure Q and HHAP Funds to See Wood Street Facility Through to Its Termination Date at Year End
The City’s Wood Street homeless intervention, which was initially created to transfer an adjacent vehicular encampment and then amplified with community cabins in 2022 to rehouse another non-vehicular one, will terminate at the end of 2025. In the meantime, however, the city has run out of the allocated funding it was using to run the encampments. Council on Tuesday will consider using funding from a county-administered state grant and local Measure Q to keep the program running, and create what an accompanying report describes as a “warm handover” to other housing situations for the current tenants.
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