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WW reported on Tuesday evening that Ivory Mathews, the CEO of Home Forward, spent more than $100,000 in public dollars traveling to conferences and events over a three-year period. Her travel took place while the housing authority, tasked with providing 7,000 affordable apartments and thousands more housing vouchers to low-income Portlanders, was experiencing financial challenges and failing to fill vacant apartments on a timely basis. As those difficulties intensified, Mathews traveled out of state for roughly 45 days per year between 2023 and 2025.
But one trip among the dozens Mathews took was not like the others.
In October 2024, Mathews flew to Hawaii with a handful of family members. She stayed six nights at a beachfront resort on Kauai at $619 per night, totaling $4,767. Her round-trip flight cost $720. The rental car cost $1,529, airport parking cost $168, and two checked bags on the flight back to Portland cost $85.
Home Forward paid for all those expenses—a total cost of $7,269.
Mathews posted hundreds of photos from her trip. She and her family rode horseback on the beach, toured former sugar plantations and farms, and visited canyons. At no point on social media did Mathews, who often chronicles her travel to housing conferences and events, post about any work-related activity in Hawaii.
Mathews took at least 12 taxpayer-funded trips in 2024, and at least 14 more in 2025. But what makes the Hawaii trip stand out among all the others is both the cost and the reason for the trip.
Mathews now says she was on the island to attend a four-day conference held from Oct. 14-17 on what’s called “captive insurance.”
Rather than paying insurance companies to cover their risks, some large organizations create their own insurance companies—captive insurers. They do so in order to save money.
“To ensure stable, cost-effective insurance coverage of the largest affordable housing portfolio in the region,” Mathews tells WW in a statement, “Home Forward created a licensed self-insurance company known as Home Forward Insurance Group, which is licensed in the state of Hawaii. To ensure we could keep up on trends in the industry, I attended the annual Housing Captive Insurance Conference from October 14 through 17, 2024.”
Captive insurers are typically domiciled in one of a handful of states known for being friendly to such arrangements. Home Forward switched to a captive insurance model in 2021, a year before Mathews took the helm, joining a growing number of housing authorities making a similar change.
Home Forward could have chosen to domicile its insurance company in any number of states. Vermont is home to more captive insurers than any other state. Utah is second, North Carolina is third, and Delaware is fourth. Hawaii is fifth.
Home Forward spokesman Rylee Ahnen says the agency initially looked at a range of states and jurisdictions to set up the domicile—namely Oregon, Arizona, Hawaii and Washington D.C.—but eventually narrowed it down to Hawaii because of its “experience and well-established infrastructure.” (Oregon, Ahnen says, couldn’t guarantee setup as quickly as the agency wanted.)
“Crucially, the State of Hawaii had a framework in place for an Oregon entity to create a self insurance captive,” Ahnen says, “which ensured that we could establish in time to avoid another year of open insurance market premium increases.”
Clean Water Services, the sewage agency for Washington County, originally organized a captive insurer in Hawaii, also, back in 2016. But in November, after an Oregonian investigation of excessive travel to that state by agency staff, Clean Water Services announced it was moving its insurer to Arizona. The agency said “this followed a third-party review that determined that Arizona is currently the most favored domicile.”
In 2024, Mathews flew to Kauai three days prior to the conference’s start, and flew out the morning of the final day of the conference.
After the agency repeatedly told WW that it could not find any reimbursement receipt for Mathews’ flights to and from Hawaii, spokesman Rylee Ahnen on April 14 provided the receipt to WW for the flights totaling $720.
Ahnen says Home Forward did not pay for Mathews’ meals, and believes the receipts provided to WW are exhaustive. (The resort receipt does include two charges that appear to be from the resort’s bar and grill.)
Mathews’ travel habits were the focus of a WW story published on April 13, which showed that many of those trips were to attend conferences hosted by the National Association of Housing and Redevelopment Officials, an advocacy group that Mathews during the latter half of 2024 and much of 2025 was campaigning for a leadership position in.
At a September 2025 NAHRO conference in Phoenix, the association swore in Mathews as senior vice president for a two-year term. Home Forward flew out its entire executive team for the event.
The Home Forward Board of Commissioners has defended Mathews’ travel, with board chair Matthew Gebhardt saying the board has “full confidence” in Mathews’ leadership and that “her work at the national level helps position Home Forward to better navigate” challenges facing affordable housing providers.
Mathews, too, says her travel helped Home Forward.
“My participation in national affordable housing work ensures Home Forward is connected to best practices, peer agencies, and federal policy decisions that directly impact our funding and operations,” Mathews said. “That perspective helps strengthen how we respond to challenges locally, while our team continues to make progress on key priorities.”
