Category Archives: Campaigns

Case Country isn’t where you think it is.
But Claude quickly got the picture.

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My life change this morning. For the good. And, for regular readers-no, it’s nothing related to my current cancer treatment.

It’s the day after Hawaii’s Primary Election, and normally that involves my spending hours knee-deep in raw text files and legacy database queries.

But today was different. And that’s how the story begins.

In the past, my first task in the morning after an election, even before getting a cup of fresh coffee, would be to visit the Office of Elections’ website and quickly eyeball the tables of election data from the most recently available statewide summary of results. After a quick look through the outcomes of what were expected to be the most contested races, I would then download the text file containing raw precinct-level data also available from Office of Elections.

The next task would be to import the text file into Filemaker, a robust Mac database. My version is about five years old, but perfectly serviceable for my uses.

Once the data was downloaded into Filemaker, I could then begin converting my questions into queries instructing Filemaker how to search through and analyze the data from different directions, breaking it down to precincts or summarizing by electoral districts or neighborhoods looking for patterns. Sometimes I started with specific questions, but lots of times I just wanted to satisfy my curiosity. Occasionally I might share some findings in a post-election blog post, but more often they just provided background understanding to guide my future reporting. And many times I would be stalled out trying to write a query that produced exactly the results I was looking for.

Then the earth moved!

This morning, I skipped the whole text file/download/import/Filemaker process and decided to see how far I could get by simply letting an AI assistant do the heavy lifting.

After downloading the plain-vanilla statewide table of precinct-by-precinct results in pdf format from the elections website, I just uploaded the 498-page data table to Claude, Anthropic’s AI assistant and the dog I chose for today’s hunt.

Claude was immediately ready to rock and roll!

I had been surprised to see how handily Congressman Ed Case had fended off what appeared to be a strong challenge from State Senator Jarrett Keohokalole, and wanted to know more about voting in their head-to-head race.

Working with Claude was seamless. I started asking questions, and Claude began returning clear, detailed answers instantly.

How many districts within Congressional District 1 did Keohokalole carry?

Claude’s answer–None.

Case ran the table, winning every one of the 25 legislative districts that make up the Congressional District 1. Claude did not include the two districts that are split between CD1 and CD2 because they didn’t fit my initial question.

And Claude provided an unexpected takeaway. The areas where Case showed the greatest strength are not where most observers might assume they would be.

Key takeaway: This is a stark geographic story.

Case’s biggest margins over Keohokalole are almost entirely in Leeward and Central Oahu — Waipahu (District 36) crushed it at +40.5 points, followed by Kalihi, ‘Aiea/Halawa, Pearl City, and the Mililani corridor. These are working-class and suburban communities, not Case’s presumed home-turf advantage neighborhoods.

Notably, East Honolulu districts (18, 19, 20) — where you’d expect an incumbent’s strongest home support — only rank #9–12 on this list, with more modest margins (+16 to +20 points) despite being generally considered “Case country.” His dominance was actually strongest in the areas furthest from town.

Only 2 districts (21 and 46, not shown in top 25) had narrower margins below +8 — Case won every single House district in the congressional district, just by varying amounts.

In 1976, I doubt this geographic pattern would have been any surprise, as the leeward area at that time was considered the stronghold of the AJA-generation of Democratic Party organizers credited with the behind-the-scenes grassroots work that powered the party’s rise to political dominance. But the public perception is quite different today, making these findings somewhat startling.

Here are the districts where Case outpaced Keohokalole by the largest percentage margins. The full list can be found here.

I chose Claude for this assignment more or less at random, and I expect other AI assistants would provide more or less similar answers. That’s probably a hypothesis worth testing another day. What I keep coming back to, though, is Waipahu and Leeward Oahu. The strongest support for this four-term congressman considered to be at the more conservative end of Hawaii’s Democratic Party spectrum strongest ground wasn’t in the politically purple districts in East Honolulu — it was in the traditional Democratic Party strongholds from Pearl City to Waipahu. The progressive drift of many Democratic activists appears to carry less sway out thata way.

Twenty minutes with a PDF and an AI assistant got me to that insight almost before I’d finished my coffee. A few years ago, that would have taken me the better part of a morning, if I got there at all.

Who Gives Together? Mapping Hawaii’s Political Contributors

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The recent bribery indictments that included two former powerful legislative committee chairs raised a familiar question: Who really holds the levers of power in Hawaii politics?

To find out, I turned to a massive dataset: nearly 128,000 campaign contributions made to state and local candidates across Hawaii from 2015 to 2026.

By feeding this decade of data from the Campaign Spending Commission nto ChatGPT to perform network co-giving analysis, one clear conclusion emerged:

Hawaii’s donor class doesn’t invest in ideology. They invest relationship building and institutional access.

The pattern is consistent with relationship-building and institutional access rather than strong ideological alignment.

Mapping “Portfolio Similarity”

When analyzing campaign finance, looking at who cuts checks on the exact same day is rarely where the real story lies. The strongest evidence of donor alignment comes from persistent portfolio similarity—donors who repeatedly back the same slate of viable candidates cycle after cycle.

By filtering for donors who appeared in at least ten election cycles and shared eight or more candidate selections, the AI analysis isolated a core network of 577 recurring donors connected by 1,415 strong co-giving relationships, falling into 55 distinct statistical communities.

These recurring donors generally fall into three key categories:

Small Household/Partner Circles: Near-identical small portfolios, typically representing families, partners, or close business associates.

Large Institutional Networks: PACs, registered lobbyists, and government-relations executives who give broadly to viable, winning candidates.

Cross-County Executive Networks: Individuals and organizations that repeatedly support winning county mayors across different islands.

The third category is particularly telling: the common denominator isn’t shared geography or partisan ideology—it is executive governmental authority.

The Central Donor Networks

Rather than functioning in isolated industry silos, Hawaii’s donor landscape is best understood as a web of interlocking political communities.

Donor Cluster Core Participants & Sectors Primary Focus & Leverage Points
The Institutional Core Insurers, Utilities, Corporate PACs, Major Unions, Government Relations Firms Access to legislative leadership, incumbent committee chairs, and regulatory policy across Democratic factions.
Development & Infrastructure Engineering firms, Land-use attorneys, Contractors, Planning consultants County-level zoning, permitting, capital improvement projects (CIP), and procurement contracts.
Organized Labor Public-employee unions (HGEA, UPW), Building trades (Carpenters, Laborers, IBEW), Teachers Incumbent relationships, department budgets, collective bargaining, and legislative leadership support.

The Institutional Core

The most influential cluster consists of major corporate PACs, labor unions, top government relations executives, and active individual donors.

Key players in this broad access network include Island Insurance PAC, Alexander & Baldwin’s HIPAC, Local 1186 IBEW PAC, Nareit Hawaii, Hawaiian Telcom Good Government Club, Matson Navigation, HGEA, UPW, Hawaii Laborers PAC, Hawaii Regional Council of Carpenters, and General Contractors Association of Hawaii PAC. Active individuals and lobbyists appearing in this space include Bruce Coppa, Blake Oshiro, Jennifer Sabas, Ross Yamasaki, Bert Kobayashi, and Stanley Kuriyama.

Their connection isn’t necessarily about giving identical amounts on the same day—it’s about repeatedly selecting the exact same set of key decision-makers across election periods to ensure a seat at the table regardless of which faction holds power.

Development, Engineering & Professional Services

A second major cluster centers on individuals in the built environment: developers, civil engineers, land-use attorneys, and contractors.

Prominent figures in this recurring co-giving group include Patrick Kobayashi, Greg Hiyakumoto, David Tanoue, Dexter Kubota, James Yamamoto, Richard Asato, Leonard Leong, Ken Hayashida, Susan Kobayashi, and Collins Lam.

This group’s portfolio overlaps heavily around county-level governance where critical decisions on land use, infrastructure, permitting, and construction contracts are made.

Organized Labor: Overlapping, Not Monolithic

While labor unions are among the most active political donors in the state, the data shows they do not act as a single, indivisible bloc. Instead, distinct sub-networks exist—public employees (HGEA, UPW), construction trades (Laborers, Carpenters, Operating Engineers), education (HSTA), and utilities (IBEW). They converge most heavily around viable incumbents and leadership figures who control committee assignments and budget allocations.

A Note on Network Analysis & Legal Context

Co-giving patterns reflect persistent portfolio similarity—meaning these donors consistently back many of the same viable candidates over time. While this methodology identifies the institutional relationships most worth examining through public records, co-giving does not, by itself, establish improper coordination, illegal straw contributions, or undue influence.

Next Steps: Building the Full Investigative Map

Mapping campaign contribution records is just step one. To turn this donor network map into actionable investigative reporting, the next phase requires integrating six additional public datasets:

Employer Normalization: Standardizing name variations across thousands of entries (e.g., matching “A&B” with “Alexander & Baldwin”).

Corporate & Non-Profit Boards: Cross-referencing top donor clusters against DCCA corporate filings and IRS Form 990 board rosters.
Government Boards & Commissions: Overlaying recurring donor lists against state and county board appointments (e.g., Land Use Commission, HART, Planning Commissions).

Lobbying & Procurement: Matching contribution timing against registered lobbying clients, government contracts, and contested land-use proceedings.

By layering these datasets, we can move from simple campaign finance tallies to a clear, multidimensional map of how institutional influence operates across Hawaii.

But whether these data are available in a form that can be accessed for such an analysis remains to be seen.

Have a specific donor cluster, contractor, or board you’d like to see analyzed in the next phase? Leave a comment below or drop a tip.

[Original post revised at 6:33 a.m. with assistance from ChatGPT and Gemini.]

The Councilman, the Crime Boss, and the “Hostage” Trees

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Tree at Joe Lukela park claimed by Mike Miske

Now that Trevor Ozawa is again a candidate running to take back his former seat on the Honolulu City Council, voters should examine his past misuse of his political position to benefit the late racketeering boss Mike Miske.

As a voter in his district, I haven’t forgotten how Ozawa—who served on the council from 2014 to 2018—aggressively used his legislative power to muscle the Department of Parks and Recreation into giving Miske special treatment.

In a nutshell

In 2016, Miske took over a tree in a park along Maunalua Bay in Hawaii Kai and wrapped it tightly with lights. The city Department of Parks and Recreation eventually received complaints and directed Miske to remove the lights. He belatedly complied, but wanted to repeat the tree lighting in 2017 over the department’s objections.

Miske turned to the Honolulu City Council member from his district, Trevor Ozawa, who became his rather enthusiastic advocate, eventually resorting to legislative threats and insider political muscle to get Miske what he wanted. Ozawa successfully forced the city to approve Miske’s lights despite substantive opposition from the parks department that cited the danger to tree health, the administrative problems posed by privatizing park trees, the precedent affecting 200,000 other trees, and the placement of bright lights along the shoreline, which posed a threat to seabirds and appeared to violate environmental laws.
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What about the First Amendment?

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Civil Beat’s “Sunshine Blog” threw it’s weight behind House Bill 371, proposed legislation described as “the measure that would ban the owners, officers and close family members of government contractors and organizations that receive state grants in aid from donating to political campaigns.”

Apparently CB sees it as a way to put an end to pay-to-play politics.

A worthy goal.

However, in my view, CB and the Sunshine Blog are making a grave error in not taking into account the First Amendment implications of this bill.

The sweeping scope of this bill and its restrictions on First Amendment political speech is breathtaking. Despite this, the legal issues surrounding free speech in the context of political campaigns and campaign finance were not mentioned in any of the testimony during hearings on this bill.

That’s a huge omission because, if passed into law, HB371 would not simply “chill” free speech of corporations, it would eliminate the First Amendment rights of an large but as-yet-undetermined number of individuals associated with , and would trample on long-accepted legal precedents.

These issues are so glaring that the bill appears written to invite a successful First Amendment legal challenge.

Back to Basics

What happens when there’s a direct conflict between the First Amendment right to free speech during an election campaign, and the public’s interest in combatting corruption?

Political speech and expression are at the heart of the First Amendment. After all, the First Amendment’s primary purpose was to protect open discourse about government affairs. Thus, political speech usually receives the strongest protection.

This means that courts tend to apply strict scrutiny to test the constitutionality of restrictions on political speech or expression. Strict scrutiny is the most difficult standard to meet. It requires a restriction to serve a compelling government interest in the least restrictive manner.

A compelling government interest, implemented in the least restrictive manner, or at least in a narrowly targeted manner.

So let’s take a look at HB371.

It would prohibit contributions by state or county contractors, as well as state or county grantees, along with their officers or immediate family members, whether or not they have any role in the contracts or grants, or even any contact with the family member directly involved.

And immediate family members, according to the bill, includes any child, parent, grandparent, brother, or sister, and the spouses or reciprocal beneficiaries of those officers.

I haven’t seen any discussion of the loss of rights for officers of state grantees, along with their family members.

Check this list of organizations that received state grants in aid during the 2024 legislative session.

Here’s page 1 of the 4-page list of grant-in-aid recipients, just to provide a sense of the bill’s broad impact.

Somewhere about 150 community nonprofit organizations are on the list. And all of their officers, along with their parents, grandparents, siblings, and their spouses or partners, will not only be prohibited from contributing to the candidates of their choice, but from contributing to “any political committee,” or to “any person for any political purpose,” or to solicit any contribution “for any purpose.”

One glaring omission is the lack of any nexus between these sweeping prohibitions, the contracts or grants that trigger them, and any actual potential for corruption stemming from those contracts or grants.

For example, an argument can be made that a corporate contractor or grantee, and its officers, should be prohibited from making campaign contributions to the level of government that originates the contract or grant. So you get a state contract, and you shouldn’t then contribute to the governor. But why should that state contract limit your ability to contribute to the mayor’s race, or a city council race, when those positions play no role whatsoever in awarding the contracts or grants?

At one point, my father’s small restaurant supply company competed for contracts to equip school kitchens. If he had landed any of those contracts, my political rights would have been eliminated, along with those of my wife, despite there being no crossover between my dad’s Republican leanings and my own political views.

It seems to me that this is classic overreach, and far from the targeted restrictions that First Amendment analysis requires.

There are already plenty of laws prohibiting pay-to-play corruption. It’s illegal to enter into explicit or implicit quid-pro-quo understandings linking campaign contributions to discretionary action by an elected official. It’s illegal to structure campaign contributions in order to evade contribution limits, by giving money to others (employees, relatives, friends, customers, etc) that they would then contribute in their own names.

Obviously, a narrowly-targeted approach to clamping down on pay-to-play would be to substantially increase the budget for investigation and prosecution of these crimes, and they are crimes, or perhaps to prohibit all contributions by corporations to state and local candidates, as is done at the federal level.

Those are approaches which do not get into the thorny area of restricting constitutionally protected rights.

In any case, this is a discussion that hasn’t happened during the consideration of HB371.

There is also a broader issue. How do we see the political arena? Is it a system in which conflicting special-interest groups clash in a complex dance of deals, accommodations, and tradeoffs, or one in which the goal is to eliminate actual “interests” and leave decisions to neutral arbiters of the “public” interest?

But that is necessarily a discussion for another day.