Oakland has hella lawsuits
Oakland Agenda Watch, October 20, 2025 — Just can’t quit coal in Oakland; pay no attention to what’s behind the curtain; Oakland Coliseum debacle keeps giving; criminally defending city officials
Our Oakland Agenda Watch column provides short summaries of key items on upcoming public meeting agendas that catch our attention. This week, we’re reviewing the Oakland City Council’s special closed session meeting on Oct. 23, along with a few key items on the council’s regular meeting agenda on Oct. 21.
The City of Oakland gets sued a lot. Every city gets dragged into court from time to time. This is why virtually every city employs city attorneys and other legal counsel, often at significant expense. Beyond the run of the mill slip-and-fall cases, some cities seem to have a talent for catching impressively high numbers of major lawsuits. In this respect, Oakland is a hall of fame contender.
Take for example some of the items on the city council’s special closed session meeting agenda for Oct. 23. Per various carve-outs in the Brown Act (California’s public meeting sunshine law), “closed session” discussions may be held behind closed doors and public details are kept scarce. The general topics must be announced to the public in advance, and any “reportable actions” must be disclosed after the fact. But they’re unfailingly vague and cryptic, leaving the actual substance of the topics and city council’s discussions shrouded in mystery.
There are some legitimate justifications for keeping some of these details confidential, for example active litigation and sensitive personnel matters. It’s easy to imagine how these private discussions could go off-topic, while hiding from the public spotlight.
Here’s a look at some of the intriguing items listed on the closed session agenda under the generic heading, “Conference with City Attorney – Existing Litigation.”
Just can’t quit coal in Oakland
City Council closed session, Oct 23
Remember all those yard signs and rallies that popped up a couple years ago with the slogan, “Keep Coal Out of Oakland”?
This paragraph from a legal filing1 up for discussion at the Oct. 23 closed session sums up the matter succinctly:
The City of Oakland… entered into a series of agreements with Oakland Bulk and Oversized Terminal, LLC (OBOT) that gave OBOT the right to develop a bulk cargo shipping terminal at the site of the former Oakland Army Base. One of the agreements was OBOT’s ‘Ground Lease’ of property at the project site for a term of 66 years. But amid public backlash after word spread that coal might be transported through the terminal, the City moved to block coal there. Since then, the parties have been embroiled in extensive litigation—and three appeals, one in federal court.
The City of Oakland lost all three appeals.
Regardless of one’s position on coal and coal transport, this city is now in a precarious position because its city council reneged on a contract for political reasons, resulting in an expensive and distracting lawsuit, and large potential damages yet to be levied. Such damages could easily run into the tens of millions of dollars. The city and the council, like any corporation and its board of directors, must abide by the law, including the contracts it signs. And unfortunately when they do not, it’s the residents who will shoulder the cost.
Oakland Coliseum debacle is a gift that keeps giving
City Council closed session, Oct 23.
Remember the proposal a few years ago to build a flashy new ballpark at Howard Terminal for the Oakland A’s professional baseball team, before they left Oakland for financially greener pastures? The A’s aren’t the only ones who left coal in Oakland’s stocking.
At first glance, this closed session procedural item2 appears to be a mundane filing in a Kentucky bankruptcy court by a generic-sounding “insight solutions” shell company. But a closer look suggests that it is likely anything but mundane or generic to the city council, as it pertains to the massive Oakland Army Base coal debacle lawsuit. And a separate but relevant legal filing by the same company about the Oakland Coliseum deal suggests that the city council may actually find it very interesting because it appears to pertain to legal discovery, by way of the Sierra Club’s high-profile political and legal efforts to influence both deals.
Back in 2020, the Sierra Club, famous for its environmental protection efforts and advocacy, came out hard against the Howard Terminal ballpark proposal, citing environmental concerns, and it came out in favor of rebuilding a new ballpark on the site of the existing Oakland Coliseum instead.
A few years later, the Sierra Club was a prominent advocate and proponent of the “Keep Coal Out of Oakland” campaign which was centered around the ill-fated development deal at the former Oakland Army Base. The city council ultimately moved to alter that deal, leading to the present massive lawsuit.
Given the cryptic nature of closed session agendas, it’s practically impossible to divine exactly what legal exposure the city attorney and city council are concerned about that legally allows a closed session to take place. However, it is notable that the plaintiff/debtor in this case, Insight Terminal Solutions, also is involved in a separate case in which it sought to secure “unlimited discovery from the Sierra Club regarding the Oakland Coliseum.” Discovery in the legal sense means the ability for a hostile litigant to comb through the opposition’s documents and communications and secure depositions for the purpose of uncovering facts about the case.
Coming soon to Oakland Report: Talking out of school: a closer look at the Oakland Unified School District board of education. Subscribe (it’s free)
Oakland set to pay out $530,000 to settle lawsuits for a police car crash, a dangerous crosswalk, and a boat seized in the estuary
Oakland City Council regular meeting, Oct. 21
To the average person, legal settlements often make no sense. Why pay out large sums of money to settle a claim if you believe it is spurious? Why not fight it in court, thereby avoiding the payout and discouraging others from filing more spurious claims in the future? The reality is that lawyers are expensive, trial outcomes are unpredictable, and it’s often cheaper and safer in the financial sense to pay a settlement and make the problem go away. Conveniently, settling out of court also allows the government to accept no blame and the claimant to get paid, no matter if the claim is true or false. Money heals many ills and soothes many pains, and the government objectively has a lot of money, fed by an unending supply of revenue: taxpayers.
On Oct. 21, city council will vote on a combined total $530,00 in payouts to settle three lawsuits:
$350,000 to settle a case of vicarious liability/negligence. According to the city’s report, the case involves allegations that an Oakland police officer negligently ran a red light and caused a serious injury accident.
$100,000 to settle a claim of dangerous conditions on public property, in which a hit-and-run driver is alleged to have struck and gravely injured a pedestrian in a crosswalk. The pedestrian then sued the city alleging that the crosswalk was a dangerous condition on public property.
$80,000 to settle a property confiscation claim, in which the Oakland Police Department is alleged to have improperly seized and destroyed a boat that was anchored in the Oakland Estuary.
Oakland City Council to vote on using taxpayer funds to defend city officials from criminal charges
Oakland City Council regular meeting, Oct. 21
As we reported last week, the city council is set to vote at the October 21 meeting on empowering the city attorney to criminally defend city officials, including city council members and city executives, at taxpayers’ expense.
On the surface, the stated intent is to rapidly defend city employees who become exposed to criminal charges for “acts or omissions within the scope of their official duties,” such as refusing to cooperate with the federal government’s immigration enforcement actions.
This seems like a reasonable, proactive defense mechanism in some ways, but it’s worth noting that politicians and government in general are notoriously susceptible to mission creep. Legislation enacted on the premise of being merely a targeted response to a momentary crisis can and occasionally does come to be applied more widely again later, sometimes for wildly different purposes than originally intended.
One need not be a legal mastermind to imagine ways that this new power, if approved, could be creatively applied to use city funds to defend politicians from criminal prosecution for other, more loosely defined “acts or omissions within the scope of their official duties.”
For example, former Oakland mayor Sheng Thao was federally indicted for corruption and then recalled by Oakland voters last year. While there may not be sufficient political appetite to assist Thao with her legal woes now, it is not difficult to imagine a future scenario in which an amenable city attorney and/or city council could use this new power to bankroll a criminal defense of Thao (or other city officials who find themselves in similar situations) at taxpayer expense.
It is understandable, in this moment of political fear, that city officials greatly desire protection from retaliatory criminal charges due to their politics. However, giving politicians the power to spend taxpayer money on their own criminal defense, based on loosely defined terms that the politicians essentially get to interpret for themselves and for each other, would be just as corrosive to good governance as the legal threats they seek to insulate themselves from.
Oakland Agenda Watch is by no means comprehensive in our coverage of public meetings in Oakland. The scope and frequency of public meetings are far more than we can presently cover. You can review the full October 21, 2025 city council regular meeting agenda of 28 items here.
Do you have a tip about an Oakland agenda item that you think should get a closer look? We want to hear about it! Contact us at oaklandreport@citizensoakland.org.
Oakland Bulk & Oversized Terminal, LLC & Oakland Global Rail Enterprise LLC v. City of Oakland. (Alameda County Superior Court Cases No. RG18930929); City of Oakland v. Oakland Bulk & Oversized Terminal, LLC (OBOT) & California Capital Investment Group. (Alameda County Superior Court No. RG20062473).
In re: Insight Terminal Solutions, LLC, et al.; Chapter 11, United States Bankruptcy Court (Western District of Kentucky) Case No. 19-32231; Insight Terminal Solutions, LLC, as the Reorganized Debtor v. City of Oakland United States Bankruptcy Court (Western District of Kentucky) Adv. Proc. No. 24-03007.
These are important stories that are not getting any kind of coverage anywhere except here. Every Oakland voter, resident, taxpayer should be getting these reports in their mailbox.
Sean, I appreciate your writing style so much - as “The Pitt” is to hospitals, your articles are to Oakland politics. As an Oakland resident I had given up on understanding why the city is such a broke mess. You’ve made it clear and even exciting. Very glad you’re doing this!