As of today, Oct 11, 2025, Marc Benioff endorsed Trump’s leadership and said he’d support Trump deploying the National Guard to San Francisco.

Marc Benioff writes big checks in Hawaiʻi and mingles with the political establishment. He has now crossed a political Rubicon on the continent. The intersection of these facts matters for Hawaiʻi’s future.

The Salesforce guy who paid for birthing centers in Hilo is now publicly praising Trump and inviting federal muscle onto city streets. Hawaiʻi’s governor is busy threading a needle between taking that philanthropy and keeping the Trump White House talking to him. Welcome to the Venn diagram where money, optics, and state power hold hands.

For more information on the Benioff’s and philanthropy in Hawaiʻi see “Wealth, Philanthropy, and Power” in KOHALA Volume II: America.

Itʻs all about the Benjamins

Benioff’s checkbook gave Hawaiʻi hospitals beds, gear, and square footage. That matters. But his new embrace of Trump gives him political muscle that can reshape how “solutions” get sold here.

Governor Green’s job is to harvest the aid and block the overreach. Trump’s job, as ever, is to centralize power and reward loyalists. The overlap is where norms get laundered.

If you like the outcomes, you’ll call it “pragmatic partnership.” If you don’t, you’ll call it “soft capture.” Either way, it’s happening in daylight.

And yes, the machines are smiling. They always do when philanthropy oils the hinges and politics holds the door.

Benioff’s Hawaiʻi footprint, in brief

In March 2024, Marc and Lynne Benioff pledged approximately $150 million to Hawaiʻi health systems: $50 million to Hilo Medical Center and major support for Straub’s expansion via Hawaiʻi Pacific Health, in collaboration with UCSF Health. It was one of the largest private gifts in Hawaiʻi history. Hilo Medical Center was renamed Hilo Benioff Medical Center as part of the agreement.

Beginning in late 2023, the Benioffs donated hundreds of acres near Waimea to support affordable housing, including an initial 43-unit self-help project at ʻŌuli. Additional acreage followed in 2024, bringing the total to roughly 440 acres under an affordable-housing umbrella.

The philanthropy is real and significant. It builds brick-and-mortar capacity and land pipelines Hawaiʻi needs.

Josh Green’s position with the Trump administration

Since January 2025, Hawaiʻi has had to navigate a very different federal landscape. The state has worked the Washington channels to secure disaster, housing, and health resources, while contesting federal moves that threaten core programs. Governor Josh Green’s posture has been pragmatic: keep lines open for aid, push back when necessary.

Where the Venn diagram now overlaps

Benioff’s new political alignment gives him added proximity to federal power. Combined with his capital commitments in Hawaiʻi, that creates a channel where philanthropic projects can pair with federal waivers, fast-track reviews, or public-private pilots. Hawaiʻi agencies could become preferred testbeds for “innovations” that arrive bundled with data-sharing and procurement terms.

Normalizing National Guard deployments for local crime control reframes domestic militarization as “service delivery.” Once that narrative mainstreams, it migrates into state and county debates whenever leaders face pressure to “act.”

Big health and housing gifts generate public goodwill that can smooth the path for adjacent tech deployments in hospitals, schools, and state IT. That isn’t inherently bad, but it shifts bargaining power. Without ironclad guardrails, “pilots” can become long-term vendor lock-ins.

Green’s job is to harvest capital and federal support while blocking overreach on rights, data, and sovereignty. If Benioff becomes an informal translator between Hawaiʻi and the White House, expect more deals on the table and fewer easy choices.

What to watch in Hawaiʻi

Any new public-private partnerships in health, education, or public safety should disclose data flows, deletion rights, and interoperability mandates. If you can’t leave a vendor without breaking the system, you don’t own the system.

Proposals that expand Guard or quasi-military involvement in routine public order should be scrutinized against Hawaiʻi’s legal standards and historical experience. The mainland script is not always a good island fit.

Track who drafts RFPs, who consults for free, and who wins. Gifts and no-bid awards appearing in the same breath warrant extra daylight.

For the Waimea acreage, verify affordability terms, stewardship, infrastructure responsibilities, and community governance 10–30 years out. Philanthropic intent is excellent; enforceable instruments are better.

Bottom line

Benioff’s philanthropy has delivered real capacity in Hawaiʻi: hospital expansions, a renamed Hilo Benioff Medical Center, and hundreds of acres aimed at housing. At the same time, his new alignment with Trump repositions him as a broker between private capital and federal executive power. Hawaiʻi, under Josh Green, will be offered deals that promise speed and scale. Some should be taken. Some should be refused.

The test isn’t whether the check clears or the headline glows. It’s whether the terms protect public control, community voice, and long-term affordability; whether data generated by Hawaiʻi residents remains governed by Hawaiʻi law and policy; and whether “security” solutions respect rights as much as they promise results.

This is the overlap of money, optics, and state power. It’s happening in daylight. Pay attention to the paperwork.