Portland says a longtime hotel mogul failed to pay nearly half a million dollars in local taxes tied to homelessness services and preschool — and the city is now taking him to court.
According to OregonLive, the lawsuit against Shilo Inns founder Mark Hemstreet seeks about $479,000. The total includes roughly $120,000 in Metro's Supportive Housing Services tax, $355,000 in Multnomah County's Preschool for All tax and approximately $4,000 in unpaid city and county business fees, plus interest, penalties and other charges.
The city says Hemstreet failed to pay taxes for the 2023 tax year. The dispute involves two voter-approved programs that took effect in 2021 and are administered through Portland's Revenue Division.
The Bill Combines Homelessness And Preschool Taxes
Metro's Supportive Housing Services tax applies at a 1% rate to income above the applicable threshold, while Multnomah County's Preschool for All tax charges 1.5% above its lower income threshold and another 1.5% above the higher tier. The City of Portland Revenue Division lists the programs' rates and filing rules, while Multnomah County says the preschool tax also applies to nonresidents on income sourced inside the county.
Those taxes are aimed at high earners and businesses, not ordinary wage earners across the board. Metro's Supportive Housing Services program is funded by a 1% business tax on net income for companies with more than $5 million in gross receipts, along with the personal income tax.
A Hotel Empire Behind The Tax Fight
Hemstreet opened his first Shilo Inn at age 24 in 1974, building the company into a 47-hotel chain at its peak. The Shilo Inns website still identifies him as the company's founder and owner, while OregonLive describes him as being in his mid-70s and notes that the chain has contracted sharply from its former footprint.
The tax lawsuit arrives amid a broader financial and legal squeeze around Hemstreet's business interests. In 2025, the Oregon Court of Appeals affirmed a receivership order involving Hemstreet's interests in several Shilo-related entities after Cathay Bank obtained a federal judgment exceeding $4.5 million.
The appellate opinion said Hemstreet owned substantial interests in multiple Shilo Inn limited liability companies, some of which had entered bankruptcy proceedings. The receiver was given authority over certain business interests and assets connected to the earlier judgment.
What Portland Is Asking The Court To Decide
The city's current case is a collection action over alleged unpaid taxes, fees, interest and penalties. It does not establish that Hemstreet has already been found liable for the full amount; that question will be resolved through the court process.
The timing also lands as Multnomah County continues expanding Preschool for All while debating how the program should be financed over the long term. Hoodline previously covered the county's preschool tax debate, which has kept high-earner taxation at the center of Portland-area political arguments.
For now, Portland is asking the court to collect nearly $500,000 from one of Oregon's most recognizable hotel entrepreneurs. The amount remains a claim in the city's lawsuit rather than a final judgment.
