Transparency on Behalf of Pueblo

A Deep Dive into the Actions of Councilor Regina Maestri

Pueblo voters are at a critical crossroads. With municipal resources dwindling and affordable housing becoming an ever-pressing need, the decisions made by the city’s leadership matter now more than ever. Yet, what appears to be a story of representation and accountability is quickly turning into one of betrayal, self-interest, and misuse of power. At the heart of this controversy lies Councilor Regina Maestri - an elected official who has repeatedly acted against the best interests of the people she was sworn to serve.

The $1 Million Lost Opportunity

At the core of this scandal is a question Pueblo voters should demand answered: Where was her transparency when Pueblo lost over $1 million in potential affordable housing funds?

During Maestri’s first term on the Pueblo City Council, an innovative, bipartisan policy was put into place - one designed to generate revenue for affordable housing, specifically for low-income residents struggling to build or buy homes in the city. The policy was simple: The city collected about $6,000 in sales tax on materials for each $400,000 home built within city limits. Homes built in nearby Pueblo West, however, generated no such revenue. KOAA News 5

Moved by this disparity, the council approved an intergovernmental agreement (IGA) with Pueblo West. While leasing water from Pueblo Water, Pueblo West would authorize the city to collect $1,500 for every new residential building permit issued. These funds were earmarked exclusively for affordable housing. Homebuilders in the city and other stakeholders supported it, as did most of the council. Even Pueblo West leaders saw the logic - they desperately needed to lift a building moratorium caused by a lack of water and saw the agreement as essential for continued growth.

But Maestri personally opposed the agreement. After it passed by a slim margin, she and Councilor Lori Lively Winner allegedly lobbied Pueblo West board members behind the scenes, urging them to kill the deal. And they succeeded.

Today, based on the number of permits Pueblo West has issued, the city could have potentially collected more than $1 million to fund housing initiatives. Instead, that money is gone - poured into private pockets, while Puebloans face rising rent and shrinking opportunity.

Questionable Behavior Beyond the Housing Deal

The water lease issue, however, is not the only example of behavior that raises concerns about accountability and ethics. A review of Maestri’s career shows a consistent pattern of self-serving decisions, questionable ethics, and a disturbing tendency to skirt transparency when confronted with public pushback.

Political Manipulation and Questionable Alliances

In 2024, Maestri introduced a deeply controversial ordinance that would have banned abortion entirely within city limits - a move that many critics described as a political stunt designed to attract attention for her failed run for mayor. Despite warnings from the city attorney that such an ordinance would directly violate Colorado’s Reproductive Health Equity Act, she pushed it forward. Proponents believed it would inevitably be struck down in court, fueling national headlines and lining her pockets with campaign contributions. Colorado Newsline

Her support for the ordinance was particularly problematic because it ran counter to her stated mission to focus on housing, homelessness, and public safety. Behind closed doors, it felt less like policy and more like political theater - a distraction from real issues the city faces.

Distorted Public Claims to Justify Policies

During the debate on a needle exchange program in 2024, Maestri insisted there was overwhelming public support for a ban on the program, despite public records showing the opposite. A KOAA-TV report revealed that she received only three emails supporting the ban and 48 opposing it. Yet she claimed that citizens were silent about their support - a narrative clearly tailored for public consumption rather than reflective of reality. KOAA News 5

Similarly, during her push for the abortion ordinance, she repeatedly claimed the public demanded it, despite numerous groups within Pueblo mobilizing to oppose it. This raises a direct question: Was she trusted to speak for the public or was she shaping public opinion to suit her agenda?

Ethical Gray Areas and Outright Violations

The most alarming examples of Maestri’s misuse of power involve conflicts of interest and questionable ethics. In late 2024, a complaint was filed alleging she failed to recuse herself from a vote involving a $25,707 city contract awarded to Colorado Front Range Roofing - a company owned by a personal acquaintance. City law explicitly states that councilors must not vote on matters where they or their families hold a personal interest. Although the ethics complaint was eventually dismissed due to technicalities, the fact that such a complaint was filed at all raises serious concerns about her professionalism and integrity. Colorado Times Recorder

Adding fuel to those concerns, rumors - later confirmed by property tax and utility records - surfaced that Maestri moved out of District 1, the area she was elected to represent, while campaigning for an at-large seat. Voting or running for office in a different district is not just improper - it’s illegal. Official documents show Maestri leased property and transferred utility accounts under her name to a new address outside her district, a move that drew sharp criticism from community activists and political observers alike. Medium

Stifling Accountability Through Courts

Maestri’s pattern of accountability evasion extends even to her personal reactions to criticism. In 2025, she filed a restraining order against a local political activist, claiming they threatened her with physical violence. Chieftain

While personal safety measures are legitimate, critics argue that she weaponized the legal system to silence opponents and chill free speech - a troubling approach for any public servant who should welcome scrutiny and dissent as part of a vibrant democracy.

Outcomes: A Record of Controversy and Distrust

The sum total of Maestri’s record is deeply concerning. What should have been a narrative of public service and integrity now looks increasingly like a chamber of self-interest and short-term political gratification. Her actions have put the city of Pueblo in a position where:

• Over $1 million in affordable housing funds were blocked or diverted for private interests.

• A city ordinance fruitlessly challenged state law and risked taxpayer money on costly litigation.

• Conflicts of interest surrounded key contracts with personal associates.

• Public institutions like city council were used as platforms to further personal political goals.

• Community trust was eroded through repeated instances of misleading public statements.