Homelessness and Encampments, A Look Back—What Has the Portland City Council Been Doing for the Last Few Years?
By Together Portland
Portland-For more than three years, Portland has been consumed by the crisis of unsheltered homelessness and addition. Once tucked away in hidden corners of parks or vacant lots, sprawling tent encampments emerged during the summers of 2022 and 2023 in the city’s most visible and vital public spaces. With them came disorder, crime, and public health hazards that every Portlander could see: vandalized businesses, people passed out on sidewalks, drug paraphernalia scattered on playgrounds and doorsteps.
Through all of this, the Portland City Council failed to lead. Instead of responding with balance and accountability, Councilors wasted time debating whether to legalize encampments citywide and undermined the very first responders tasked with keeping our streets safe. Residents and taxpayers have shouldered the cost, while neighborhoods and businesses bear the brunt of disorder.
This is a story not just of homelessness and addition, but of a City Council that has too often put ideology ahead of solutions, leaving Portland to suffer the consequences.
2023: A City Overrun
When pandemic-era hotel shelters closed in 2023, unsheltered homelessness surged. The Bayside Trail alone swelled to nearly 200 tents. Reports mounted of individuals with homemade weapons threatening passersby, businesses broken into and vandalized, public defecation, and mountains of hazardous waste.
By May 2023, city staff were already recommending encampment clearing and referrals to the taxpayer-funded shelter network. Instead, the Council balked. Predictably, encampments simply migrated. First to Marginal Way, then the Fore River Trail, and eventually to Harborview Park under the Casco Bay Bridge, each one growing until the next inevitable confrontation.
By November 2023, over 200 tents dotted the city, 120 of them in Harborview Park alone. Despite urgent warnings from the then Mayor Kate Snyder, District Attorney Jackie Sartoris, city staff, and even the Maine Department of Transportation to clear them before winter, a bloc of obstinate City Councilors tried to push through a radical measure: legalizing camping in all city parks, sidewalks, and public property.
Order 68, as their effort came to be known, sponsored by Councilors Anna Trevorrow and Roberto Rodriguez, came up for debate just two days before Thanksgiving. Hundreds of residents packed City Hall. Hour after hour, everyday Portlanders testified: the tent cities were dangerous, unhealthy, unfair to neighbors and businesses, and unsustainable. Ultimately, by a vote of 3-6, the City Council listened to the vast majority of the public and rejected Order 68, with former City Councilors Anna Trevorrow (District 1), Victoria Pelletier (District 2), and Roberto Rodriguez (At-Large) voting in the affirmative minority.
The fallout was immediate. In December 2023, Mark Dion was inaugurated Mayor following a clear mandate to restore order, enforce existing ordinances, and connect people with shelter and services.
Undermining the Police
Another constant frustration for Portland residents has been the perception that police are not doing enough to stop blatantly illegal activity in public spaces. The truth is more complication and the City Council bears direct responsibility.
Like many cities, Portland’s Police Department saw retirements and departures after the pandemic and the 2020 protests. Officers sought lower-stress jobs, and new recruits were hard to attract. But while many departments in Maine and nationwide have since stabilized, Portland has continued to struggle with at least 30 vacancies. This is a direct consequence of certain City Councilor’s repeated refusals to back its own police force and the labor agreements they negotiate with City leadership.
The Council’s role is critical. It sets the terms and votes on collective bargaining agreements that determine pay, benefits, and working conditions for city employees, including police. Instead of supporting the force and these agreements, Councilors have turned these votes into political battles.
- In November 2023, on the very same night they debated legalizing citywide encampments, the Council took up Order 69, the contract for the Police Superior Officers Association. While it passed 7-2, Councilors April Fournier and Victoria Pelletier voted against giving Portland’s police leaders competitive pay and benefits.
- In May 2025, when that contract came up again, it passed 7-2, but this time with Councilors Wesley Pelletier and Regina Phillips opposed.
- Just months later, in July 2025, the Police Benevolent Association contract, covering the rank-and-file officers already stretched thin, barely passed 5-3. Again, Pelletier and Phillips opposed fair compensation, and this time they were joined by Councilor Kate Sykes.
These repeated “no” votes against both supervisors and rank-and-file officers sent a demoralizing message: Portland’s elected leaders will not stand together with the very men and women asked to handle the impossible burden of encampments, drug crime, and disorder. For residents and businesses watching their neighborhoods decline, it was another example of misplaced priorities. Instead of supporting first responders, these Councilors made their jobs harder, ensuring vacancies persist and public safety suffers.
2024: A Brief Return to Order
Mayor Dion wasted no time. In December 2023, Harborview Park was cleared, and for the first time in years, no encampments persisted. City staff reported in early 2024 that illegal camps were being dismantled quickly and individuals directed to services.
The results were clear. In January 2024, for the first time in years, the city recorded zero overdose deaths. Shelter staff administered Narcan, saving lives. Experts like Cullen Ryan of Community Housing of Maine confirmed what should have been obvious, the only path forward is to bring people inside and provide services, not to enable dangerous encampments.
The City made real efforts to adapt, extending shelter curfews to 11 pm, adding transportation, improving storage for belongings. For a brief moment, order and compassion worked hand in hand.
Addiction, Needles, and Council Indifference
But as visible encampments subsided, a new and equally troubling reality set in, with discarded needles scattered citywide, from alleys to doorsteps. Disturbing videos emerged, including one showing schoolchildren walking past unconscious addicts outside a Bayside apartment building.
The Mayor repeatedly called for action, including a return to a one-for-one clean-to-used needle policy. Yet instead of taking the problem seriously, Councilors downplayed it. Councilor Kate Sykes even described scenes of addicts passed out in public as “beautiful moments of human kindness.” Others dismissed the risks of discarded needles entirely, suggesting residents simply pick them up themselves.
When Resolve 4 to restore one-to-one exchange came before the Council in October 2024, it failed in a 1–7 vote. Mayor Dion stood alone.
The Record of Inaction
This is the legacy of the Portland City Council’s handling of homelessness and addition:
- Allowing sprawling, lawless encampments to dominate neighborhoods and parks for years.
- Undermining the Police Department with votes against fair contracts, leaving dozens of officer positions vacant.
- Ignoring public health and safety concerns about discarded needles and dismissing the dangers to families and children.
- Prioritizing ideology and political posturing over practical solutions.
Portland is a city rich in the resources of shelters, services, and treatment options funded by taxpayers. But resources mean little if elected leaders refuse to enforce order, support first responders and connect people with the help they need. Residents, businesses, and even the most vulnerable on our streets have suffered for years under a City Council that mistakes inaction for compassion. True compassion means safe streets, orderly neighborhoods, and connection people with services, not leaving them to die in tents or on sidewalks.
It’s time for leadership that restores order, respects taxpayers, and ensures Portland is both compassionate and safe. Our city cannot afford another year of the Council’s paralysis, and together we will ensure they act.
The Tally: Key City Council Votes on Homelessness 2023-2025
The key votes by councilors are tallied in the table below. Any votes listed as N/A** fell outside of a councilor’s term. Absent votes are indicated.
