Prominent Homelessness Critic Kevin Dahlgren Pleads Guilty to Theft, Ordered to Repay $16,000 to Gresham

Kevin Dahlgren, a prominent social media personality and outspoken critic of Portland's homelessness services, recently pleaded guilty in Multnomah County Circuit Court to charges of first-degree theft, aggravated identity theft, and first-degree official misconduct. The admission, which occurred in January 2025, stems from his misuse of city funds during his employment as a homeless services specialist for the city of Gresham. Dahlgren, 54, received a five-day jail sentence and was ordered to repay $16,000 to the city as part of his plea agreement.

The charges against Dahlgren, initially numbering 19 counts in a grand jury indictment from October 2023, centered on his illicit use of a city procurement card. He admitted to purchasing personal items, including groceries and gas, and then fabricating identities of non-existent individuals to disguise these expenditures. This fraudulent activity led to his resignation from his $80,000-a-year position with Gresham in March 2021, following concerns raised by his supervisors.

Dahlgren cultivated a significant online following through viral videos that often depicted drug use and disorder in Portland's Old Town, using these platforms to critique what he termed the "homelessness industrial complex." He frequently argued that existing services enabled rather than solved the crisis, positioning himself as a "truth-teller" against liberal Oregon policies. This public persona, however, has been significantly undermined by his admitted actions of defrauding the very public funds intended for homelessness services.

Beyond Gresham, Dahlgren's work also drew scrutiny when the Deschutes County Sheriff's Office paid him nearly $19,000 for a controversial report on their homeless population, which many service providers deemed misleading. The legal outcome in Multnomah County includes a five-year probation period, with Circuit Judge David Rees stipulating that Dahlgren could withdraw his first-degree theft plea if restitution is paid within 90 days. Despite these legal challenges, Dahlgren continues to publish articles and maintain his social media presence, recently tweeting, "I wrote an article about it here," indicating his ongoing engagement in public discourse.