Aloha

I wrote a while back about the shocking salaries being paid to the people running Portland's public housing projects, and pretty much running them into the ground. The CEO of the housing authority, Ivory Mathews (pictured), reportedly makes more than $342,000 a year, plus $600 a month for a car, and who knows what-all else by way of fringe benefits. Sophie Peel of the Weed was responsible for digging up those gems, and over the last couple of weeks she's excavated further, into the outrageous "business" travel being racked up by Mathews at the expense of the agency, so trendily named Home Forward.

It seems that Mathews, like her peer, city administrator Raymond Lee, loves jet-setting around to conferences. 

Between 2023 and 2025, a review of public records reveals, Mathews spent more than $100,000 in public dollars on travel, including airfare, hotels, meals, extra checked luggage, and Uber fares. Home Forward paid Mathews’ travel expenses out of its operating budget.

In 2025 alone, Mathews made at least 14 taxpayer-funded trips outside the state—and at least eight were to NAHRO conferences.

On one recent trip, Matthews reportedly headed off to Kauai with family in tow, to ride horses on the beach and live it up, with the taxpayers picking up a $7,269 tab. The supposed business reason: Home Forward has a captive insurance company, which happens to be licensed in Hawaii.

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 now says she was on the island to attend a four-day conference 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.”

When I read that, I had to laugh. "Captive insurance," when practiced by private businesses, is more often than not a tax scam. When a government entity does "captive insurance," there's ususally not a tax savings to be had, but a lot of third parties are sure make a profit while the government might possibly save some dough. The idea is to cut out the insurance companies and pay small claims yourself. But to do that, you have to pay somebody to administer the program, and that can create a lot of overhead.

Apparently Hawaii is a decent place to set up one of these schemes, but the "captive" company, which exists entirely on paper, can be run remotely for the most part. There's clearly no need for a six-day junket. Mathews supposedly went to a conference that was totally optional, and she could have watched it on Zoom from her home, which reportedly is in Tigard. 

There are quotes in Peel's first story from the chair of the agency's board, who's totally behind Mathews. But when you look to see who the chair is, it's some dude on the middle rungs of the Portland State urban "planning" faculty. He's studied public housing, yada yada, okay. And who are the other board members? Two Port of Portland types, a Metro type, a couple of developer fronts, you get it – the usual suspects.

The website says there are three vacancies, and the mayor of Portland can fill them. He ought to – with people who can clean up the mess at the top. Sooner or later Mathews seems likely to get a big payout on her way out the door; the only question is when.

Her travel scandals notwithstanding, it would be interesting to know more about Portland's "captive insurance" setup. With the name "Home Forward Insurance Group," it doesn't sound like a pool with other housing authorities, but instead just Portland going it alone. Is that a sound idea? Is it legal for Home Forward to do it? What kind of risks are the agency assuming? What disaster coverage are they purchasing, and at what cost? Has the plan in fact been saving money? 

And most importantly, who are the consultants, insurance brokers, lawyers, and God-knows-who-else sucking fees off the thing? It may be totally innocent. But this is Portland, and so I doubt that. When government around here gets creative, there's usually some sort of weasel angle not too far below the surface.