The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Sunday, September 7 2025

The Rich Got a Break. Working People Got the Bill. It’s time to Re-Balance the Books.

You may have heard by now that Portland just completed a citywide property revaluation, and new tax bills will be arriving in mailboxes any day now. Residential property values went up by an average of 43% while commercial rates rose only 19%. The mil rate (the tax rate per one thousand dollars of assessed value) has been lowered to $11.98, but that doesn’t mean your bill will go down, especially if your property value jumped significantly.

For many households, this will mean a higher cost of living in a city that’s already difficult to afford. It raises serious questions about tax fairness, economic stability, and how we protect long-term residents from being priced out of Portland.

And it speaks to the core of what’s broken in American politics.

For decades, the Democratic Party has told working people that the only way to fund public services is to raise taxes on the middle class, while avoiding real fights with the wealthy and powerful. Meanwhile, the Republican Party has slashed taxes for billionaires and corporations and paid for it by cutting the programs working families rely on.

I believe we can do better in Portland. We can tax those who can afford it, and use that revenue to help everyone: renters, working-class homeowners, seniors, and low-income families just trying to stay housed.

That’s why I’ve been advocating for the Finance Committee to expand the Portland Senior Tax Equity Program (P‑STEP). At our upcoming meeting on Wednesday, September 11, the committee will begin formal discussions about how we can do that responsibly, effectively, and equitably.

What Is P‑STEP?

P‑STEP is a local rebate program that supplements the Maine Property Tax Fairness Credit. It was originally created to help low-income seniors stay in their homes as costs rose around them. Since then, more and more seniors are using the program, but today the need goes far beyond this one age group.

What’s Being Proposed?

I’m asking the City to expand P‑STEP eligibility to all income-qualified residents—not just seniors—and to do so gradually over the next five years by:

  • Lowering the age threshold each year, until it’s fully removed in FY31.
  • Continuing to include renters and expand outreach to them, so they know how to access their rebate.
  • Keeping the program revenue-neutral by modestly adjusting the property tax rate so that those with the most valuable properties help fund relief for those with the least room to spare.

I’ve also asked the Finance Committee to request a formal mil rate modeling analysis from City staff, so we can understand what adjustments would be needed to make the expanded program work, without increasing the City’s budget.

Why Now?

Because the moment demands it.

Trump’s federal tax policy rewards the wealthiest Americans while shifting the burden onto working people. Local governments like Portland are left to pick up the slack, with fewer tools and tighter budgets every year. Increasingly, that gap is becoming unmanageable.

But all politics is local, and here in Portland, we already have the tools to fight back. We can expand an existing program that works, and help the people Trump left behind. We can rebalance the equation, right here, right now.

Make no mistake: there will be pushback. Some of Portland’s biggest property owners and corporations will try to keep passing their responsibility onto the rest of us. Some folks who’ve done quite well will claim they can’t possibly give more. But I didn’t run for office to protect the powerful. I ran to fight for working people.

So let’s get ready, with facts, with fairness, and with a plan. Tune in to the Finance Committee meeting on Thursday. Write all of your Councilors and the Mayor. Share this newsletter. Let’s move this forward together.

Finance Committee Meeting
Thursday, September 11
Time 5:00 pm
Remote Via Zoom

Thank you for being engaged and for continuing to demand fairness in how we govern. I’ll keep you posted as this conversation moves forward.

ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Friday, September 5 2025

ONE BIG THING:

This week, the City Council passed a Commercial Vacancy ordinance that will put us one step further toward helping Congress Street live up to the name “Arts District.” Here’s what it does:

If a ground-floor commercial space in the Pedestrian Activities District sits empty for six months or more, the property owner is required to:

  • Register the space with the city
  • Put art in the window (provided and paid for by the City!)
  • Or, if they don’t want to do that, pay a modest vacancy fee

The registry lets our Economic Development team stop playing defense and start shaping a future. By tracking vacancies and building relationships with property owners, the City can connect artists, entrepreneurs, and cultural groups with space and support.

Some people have said that window art won’t solve anything, but boarded-up windows don’t just make a city feel sad; they make it vulnerable. They say, nothing is happening here. No one cares. This ordinance gives us another tool to revitalize the downtown.

QUICK HITS

Rent Increases Capped at 2.2% for 2026
Thanks to Portland’s rent control law, tenants will be protected from large increases next year. The cap is based on the local cost of living.

STRs Reforms Have Kicked In
The City has finalized the limit for non-owner-occupied short-term rentals on the mainland: 293 units citywide for 2026 (down from 400 in 2025) and will continue to be capped at 1.5% of our long-term rental stock. That’s how we preserve housing for actual residents.

ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Thursday August 21, 2025

When Portland’s Values Are on the Line, So Am I
Portland, Maine – August 2025

Last night, the Portland City Council met in executive session to confront yet another assault on local government from a federal administration that has already moved to defund food assistance, education, and healthcare, and now seeks to tie federal transportation infrastructure grant funds to political obedience. This wasn’t just about money to maintain our airport infrastructure. It was about whether cities like Portland will be forced into complicity with federal immigration enforcement.

The Department of Transportation has told us: if you want this grant for the Jetport, you must “cooperate” with and “not interfere with” ICE. The documents arrived electronically, with no opportunity to clarify the meaning or negotiate the terms. There was no discussion. Just a choice: sign, or lose the money.

Some of my colleagues believe signing this agreement keeps us in the legal fight. It’s true that Maine has joined a multi-state lawsuit challenging this coercive provision, and for now, a federal injunction blocks its enforcement. I respect that view.

But I believe that if staying in the fight means compromising our values, we’ve already lost. These are impossible decisions we are faced with, but I believe it is a mistake to accept terms that directly challenge our city’s autonomy without so much as a public conversation about it.

I also want to be very clear about something that is often missed in news reports: Portland follows the law. We will continue to follow the law. We comply with judicial warrants, and we do not obstruct lawful enforcement. But we also know that ICE agents do not need warrants to access public spaces, and that many people are unaware of their rights. We must ensure that the limits of federal power are understood and upheld, and that there is no further erosion of our right to self governance. Silence, confusion, and passive cooperation only makes their reach stronger.

The Tenth Amendment exists to ensure that cities and states have the right to govern themselves. That right is now under attack all over this country. Right here in Portland, masked agents are removing people from our streets without explanation. ICE vans arrive and depart without notice. Our community is left to wonder: who’s next? And now we are being told to step aside.

The courts, once imagined as guardians of constitutional balance, have too often sided against local self-determination when it matters most. We cannot count on them to save us. We must act ourselves.

Here’s how:

  • Expand local protections: Strengthen Portland’s existing limits on city resources being used for federal civil immigration enforcement unless supported by a judicial warrant.
  • Advance a Visibility Ordinance: Require federal agents operating in Portland to clearly identify themselves and prohibit masked or anonymous immigration enforcement unless an imminent public safety threat exists.
  • Create safeguards in contracts: Ensure transparency in federal grant agreements, so no future provision can quietly deputize the city without the public’s knowledge.
  • Stand together: Join Boston and other cities in a public, united resolution to affirm our right to local self-governance and demand an end to federal overreach.

I didn’t choose this fight. But I will not walk away from it.

I stand with Boston. I stand with sanctuary cities across the country. And I stand with my neighbors in Portland.

ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Wednesday August 13, 2025

The Arts Community Just Ripped Open a Conversation Portland Desperately Needs to Have

This week’s Insider is more of an open letter of gratitude to the arts community for coming out in force on Monday night to testify on the music venue moratorium. That meeting was unlike anything I’ve ever seen in City Hall. Council chambers were overflowing, two additional rooms were filled, and the energy was electric. The testimony was passionate, heartfelt, often hilarious…and everyone knew how to use a microphone. Seriously, most people who testify at public comment either won’t touch the mic or fumble with it like it might break. You all grabbed it, twisted it, found your level, and went for it.

You didn’t just “show up,” you showed up exactly when it mattered, and more than once. (Sorry again about the AV problems at the last meeting. In hindsight, we should’ve just handed the board over to you. Clearly, you know more than we do.)

All of this effort and energy and expertise made it impossible for this conversation to be swept under the rug. But I need to get real with you for a minute, because I think we’re at a tipping point and I want to speak plainly about that.

It’s tempting in moments like this to see two sides: the “No to Live Nation” side and the “Yes to the Arts” side. When a powerful corporate entity rolls into town, the threat is obvious, urgent, and it can galvanize opposition. That framing is useful for organizing, but it has its limits. A deeper truth at play here is that the fight for a thriving arts scene in Portland isn’t just about stopping something; it’s about building something better. We need to immediately pivot to that fight, and here’s why: Portland starves it’s artists.

For a city that prides itself so highly on the arts, we drastically underfund our creative community. We rely heavily on private philanthropy, but the public dollars we contribute are paltry compared to other cities. In a country that has been propagandized into seeing taxes as a “burden” rather than a powerful force for good, some think turning to private donations is a reasonable solution. I think it’s insulting.

National data from the NEA and Americans for the Arts reveals just how wide that gap it: Minneapolis invests roughly $8–$9 per resident, San Francisco more than $20, and Providence $6–$7. Here in Portland, we’re at only about $1–$2 per person. The state as a whole ranks 35th in the nation for public arts funding, spending just $0.79 per resident, compared to what Massachusetts spends: $4.46.

Non-profits can do a lot to fill gaps, but this chronic underinvestment from the public realm makes it harder for artists to thrive, limits the cultural vitality of our neighborhoods, and leaves us far behind peer cities that see the arts as essential to their economy and identity. If we say we value the arts, our budget needs to reflect that. And here’s the punchline: any community benefits agreement we negotiate with a large entertainment venue should include substantial public matching funds, so that we’re not just relying on the private market to uphold a public good. Without that, we risk building our cultural future on a swamp.

For me, that is reason enough to slow things down, take stock, and use this moment as a turning point for real investment in our creative community. That’s why I voted in favor of the moratorium and where I will be focusing my efforts from here.

Let’s Make Time for Dreaming
I recently spoke with someone who helped shape the original 1980-90s vision for the Arts District on Congress Street. Back then, it wasn’t just about banners and branding, it was about a thriving, city-supported ecosystem. A place where artists could afford to live and work. Where storefronts and public spaces buzzed with creativity. Where city government championed the arts as part of civic life.

Fast-forward to today, and much of that vision has faded or is outmoded. City-produced materials are generic, stripped of the artistic voice we claim to celebrate. Our civic events are often safe, predictable, and flavorless, the opposite of what art should be. And we’ve “art-washed” Congress Street, draping it in the language of culture while expecting artists to provide the vibrancy without giving them the resources, space, or stability to do it.

Meanwhile, Congress Street is facing vacancy, empty office buildings, reduced foot traffic, and concerns about safety and drug activity. These conditions could be the perfect catalyst for an arts-led transformation, but only if we move from branding to building. The new vacancy ordinance we’re working on could link artists directly to property owners, turning empty spaces into creative incubators. But it will only work if we give it your energy, your vision, and the resources it needs to succeed.

If we want a bold, thriving Arts District in Portland, we need to dream it first…and then organize relentlessly to make it happen.

Where We Go From Here
This moratorium fight isn’t just about one company, one building, or one vote. It’s about whether Portland is ready to treat the arts as a public good, just as essential to civic life as schools, parks, and roads are.

You’ve cracked the door open for that conversation. Now let’s blow it off the hinges. Let’s demand city budgets that match our rhetoric. Let’s integrate art into all municipal work. Let’s update the Arts District vision for 2025 and beyond. Let’s build structures where artists are decision-makers, not afterthoughts.

You’ve shown the power of organizing around a common cause. Now, let’s keep going. Let’s make “Yes to the Arts” more than a rallying cry. Let’s make it the way we govern.

ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Wednesday July 30, 2025

The Kids Are Alright: Talking Social Housing on Blunt Youth Radio

Long days, warm nights, beach reads, birdsong—and lots of visitors. Summer in Maine is sublime, and so fleeting. I hope you’re soaking it up! My soundtrack to the season has been Animaru, the latest album from the incredible jazz-influenced indie J-pop artist Mei Semones. It’s the perfect blend of dreamy and defiant, and I recently I had the pleasure of chatting about new music and housing justice with the sharp young minds at Blunt Youth Radio on WMPG. We had an energizing conversation about Portland’s housing crisis and the bold solutions we need. We talked about the harsh reality young people are facing: with more than half of Portland renters spending over 30% of their income on rent, housing is simply out of reach for too many. I explained how this affordability crisis is a direct result of relying on the private market to do all the heavy lifting, and why we need public solutions to meet the scale of the problem. We discussed Portland’s inclusionary zoning law, which requires new developments to include affordable units and why it’s so important to defend and strengthen policies that put affordability front and center. I also shared exciting news: we just seated a 13-member Social Housing Task Force to explore how Portland can become a public developer and build the kinds of permanently affordable homes the private market can’t deliver on its own. We looked to models around the world where public funds are used not just to build one project at a time, but to revolve those investments, building exponentially more housing over time, without giving away public value. It was a great reminder that the next generation gets it, and they’re ready to build a better future. To listen, click the July 17th show.

ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Sunday July 13, 2025

What’s Up with the Federated Settlement? Here’s Why It Matters (and Why It’s a Big Deal for Portland’s Future)

As someone who’s been working closely on housing policy and helped launch our new Social Housing Task Force, I want to offer some context on this week’s big news: the City of Portland is settling a 14-year legal battle with Federated, the Florida-based developer who never followed through on the Midtown project in Bayside.

So what happened?

Back in 2011, we sold valuable city-owned land to Federated, who promised a ton of housing, retail business space, and a parking garage. But despite having approvals, they never pulled permits, and the project expired. Portland taxpayers, meanwhile, kept paying interest on a federal loan for a garage that never got built. We eventually used eminent domain to take back one lot (Lot 6), and Federated sued us—for $15 million. Then we sued them too. It’s been tangled in court for years while Bayside sits there looking like Escape from New York—just overgrown weeds , busted concrete, and rusted-out fencing on some of the most valuable, transit-connected land in the city.

Now, the settlement: we’re paying Federated $15 million to get back all the Bayside land—not just Lot 6, but Lots 1, 3, and 7. This avoids a prolonged legal fight and gets the land back under public control.

Why does this matter?

Because Bayside is strategic. It’s downtown-adjacent, transit-connected, and newly zoned under ReCode to support dense, walkable development. This is exactly the kind of land where we could do something amazing—like build social housing that stays affordable and permanently off the speculative market. We’ve got the tools now: task force seated, policy momentum building, and a public hungry for real housing solutions.

But let’s not sidestep the truth here: Portland got burned on this deal a decade ago. Federated was an unknown developer, and they didn’t deliver. This is a cautionary tale about what happens when we hand over public land to private interests without safeguards. In this case, we’ve clawed back land that should never have been lost—and we did it before a drawn-out lawsuit could paralyze progress even longer.

I say we make sure we don’t waste this second chance. Let’s dream bigger for Bayside. Let’s invest in public land for public good—not more luxury units, not more empty promises.

What would you like to see built there?


ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Tuesday June 24, 2025

The Power of Us: Investing in Portland’s Shared Future

Last night, the Council unanimously passed a budget for Fiscal Year 2026 that reflects our values and our commitment to one another—even in the face of growing disinvestment from the state and federal government.

This has been a difficult budget season. The Trump and Mills administrations have advanced austerity budgets that cut deeply into public services: health care, housing support, labor protections, and General Assistance among them. These are not savings. They are costs shifted downward and cities like ours are left to pick up the slack. The conservative agenda calls this “efficiency”; in practice, it redistributes wealth upward and pushes hardship down onto those with the least.

Despite these pressures, we held the line. We passed a zero-balance budget. We pulled from fund balance to meet our obligations. We made tough choices. But we did not give up on our values. And when the City retires its pension obligation bond debt in the years ahead, we’ll begin to recover more flexibility in future budgets.

But here’s what gives me hope: Portland is on the verge of transformation. Thanks to ReCode and a renewed demand for urban living, we are poised for a new wave of development. And this time, we’re prepared.

We’ve put strong protections in place—not just to prevent displacement, but to push back against the kind of cheap, extractive development that saddles working people with long-term heating and cooling costs and accelerates the climate crisis. Policies like rent control, inclusionary zoning, the Green building codes, Vision Zero, and transportation overlay districts are reshaping the rules. We’re not just building more—we’re building better: housing that’s efficient, affordable, connected, and climate-resilient.

We’re planning for growth, and we’re planning for the prosperity to be shared.

Social Housing Task Force Seated

Last night the Mayor announced the members of the newly seated Social Housing Task Force, a critical step forward for housing justice in Portland. This task force is grounded in values: care, community, and collective responsibility. I want to thank the Housing and Economic Development Committee for advancing this initiative with urgency; the Mayor and the selection team for assembling a thoughtful and diverse task force; and the many residents who stepped forward to serve. Your leadership is the heart of this work.

Quick Hits: Child Care, Housing, and Equity

Child Care Vouchers Extended
Councilor Bullett’s budget amendment last night adds $100,000 to extend the Portland Child Care Voucher Collaborative through FY27. This ensures support for families who fall through the cracks of state subsidies.

Before & After Care Expanded
Councilor Grant’s amendment funds four new Rec Programmer positions, opening up 64 new child care slots during critical out-of-school hours.

These two amendments hint at something bigger: that we’re laying the groundwork for a universal early childhood education system. It’s ambitious, but possible. Quebec did it—and did it well. A recent Guardian article highlights how their universal child care system now serves as a model for equity, labor force participation, and long-term economic returns. Ironically, their system was inspired by U.S. research. It’s time we learned from their success.

Doubling Down on Rental Inspections
The Council voted in favor of Councilor Grant’s amendment to add funding for a second rental housing inspector. This will allow better enforcement of housing safety and code compliance citywide. At our recent workshop on rent control enforcement, we heard clearly from tenants: enforcement is critical to the success of our policies.

Council Wages Adjusted for Equity
Modest increases to Council and School Board pay will improve fairness and remove financial barriers to public service. Local government should be accessible to everyone.

Community Engagement Coordinator Funded
Councilor Phillips’ amendment creates a new position to support deeper, more meaningful public engagement. This role will help connect residents to City decisions and ensure community voice is embedded in our work.

What’s Next?

This moment marks the halfway point of my Council term. I feel really good about what we’ve built together so far—and hopeful about where we’re going. Portland is evolving. We’re growing and changing, and that means we’re healthy.

I hear from a lot of people who think the only answer to our budget constraints is to cut, cut, cut. If you’re one of them, I want to say respectfully: I don’t agree. The idea that public services are wasteful and inefficient is everywhere—but it’s a misleading story, designed to erode trust in government until that story becomes a self-fulfilling prophecy. The truth is, public services are the foundation that make opportunity, safety, and dignity possible for all of us.

Taxes are how we participate in this shared project. They’re our membership fee in something bigger than ourselves—and what we pay into that system comes back to us in the form of strong schools, safe streets, clean water, public parks, and community care.

At the same time, if you’re on a fixed income and worried about whether you can afford to stay in Portland, I hear that, too. Taxes must be fair. That’s why I’m working to advance progressive revenue tools like the expansion of the P-STEP program and a Payment in Lieu of Taxes (PILOT) program.

Portland works best when it works for all of us. If you believe that too, let’s keep building it together.


ksykes@portlandmaine.gov 207-558-5764

Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

Tuesday June 3, 2025

Reading Toward a Better City

The City Council had a relatively light agenda this week, but we did pass a few meaningful items last night that I want to highlight:

  • We approved the Storefront Improvement Revolving Loan Program (Order 224-24/25), a Portland Development Corporation initiative that will help small businesses revitalize downtown. This program will complement the Vacancy Ordinance currently under review by the Housing & Economic Development Committee. It’s one of several tools we’re working on to bring energy and commerce back to the downtown core.
  • We formally appointed a new IT Director. Phil Doughty was confirmed to the role. While he’s already been serving in the department, I’m particularly interested in learning more about his vision for safeguarding public data. Cloud-based systems and outsourced platforms raise questions for me about who controls city data and what contracts we’re locking ourselves into.
  • We received the Rent Board’s annual report. This comes just in time for the Council workshop on Rent Control enforcement happening next Monday. That meeting will explore how well our policies are working and what enforcement gaps may still exist.

We also postponed the final city budget vote to June 23, which gives me a little space to share something else that’s been on my mind: how we think and talk about growth, government, and the role of public institutions in shaping our future.

I’ve been reading three books that are informing how I approach this moment of transformation for Portland. A constituent recommended The Architecture of Urbanity by Vishaan Chakrabarti, and I’m so glad he did! It’s a visually stunning, philosophically grounded book about the role of design in shaping human relationships—how public infrastructure can foster what Chakrabarti calls “positive social friction.” That is: buildings and neighborhoods that invite us to rub up against difference, meet people we might otherwise never meet, and grow more fully into our shared humanity.

I’ve been reading it alongside Abundance by Ezra Klein and Derek Thompson (currently gracing about 1 in every 5 Democratic nightstands, I suspect) and Why Nothing Works by Marc J. Dunkelman, a deeper dive into the history of American infrastructure policy and our increasingly fractured political psyche.

Each book is part of a bigger conversation: about how we build, what we fear, and who we’re building for.

Abundance and the Seduction of Speed

Abundance makes the case for getting government out of its own way by streamlining approvals, clearing the path for new housing and clean energy projects, and reclaiming the spirit of Roosevelt-era building. It argues that our permitting and environmental review systems, while well intentioned, are now so cumbersome that they paralyze progress.

While I appreciate the urgency of that message, I also share the concerns of many on the Left who worry that this so-called “abundance agenda” is just neoliberalism in new clothes. If we build without equity, we build for gentrification. If we innovate without redistribution, we widen the wealth gap. Abundance skirts these hard truths. It gestures at justice, but avoids the structural analysis that real change demands. It’s an easy read. ( Perhaps too easy.) It packages ambition in the language of uplift, while sidestepping the politics of extraction, power, and ownership. That makes it palatable for a liberal moment desperate for hope but unwilling to confront its complicity. Maybe that’s why it’s so popular. It’s not fluff exactly, but it is politics with the rough edges sanded off.

Why Nothing Works and the Slow Death of State Capacity

Why Nothing Works offers something deeper and more provocative. Dunkelman starts with a premise everyone can agree on: something in our country no longer works. Big, complex public projects that once took years now take decades, if they get built at all. Infrastructure is crumbling. Agencies are hamstrung by bureaucracy. Trust in institutions has collapsed. And despite the fact that most of us agree we want functional schools, safe housing, reliable transit, thriving neighborhoods, we remain stuck, unable to course-correct or rebuild the systems we need to make those things real.

Dunkelman traces this dysfunction to a political over-correction. Progressives, in an effort to hold power accountable, stripped it of its ability to act. We moved too far in the Jeffersonian direction, toward endless checks, veto points, and community input processes that prevent anything from being built at all.

He walks us through a dizzying number of examples: transmission lines blocked for years by lawsuits, a single public toilet in San Francisco that took ten years and $1.7 million to install. These aren’t just punchlines; they’re symptoms of a system that has over-corrected so far toward “saying no” that it’s forgotten how to say yes.

Dunkelman pushes us to confront a harder question: Who decides what gets built, what gets sacrificed, and according to whose values?

He argues that government has a responsibility to build—even when building causes discomfort. That progress always involves burdens. If government can’t ensure that people have access to affordable homes, then we have to question whether it’s doing its most basic job.

It’s a hard message for progressives to hear, but an essential one. As he puts it, progress requires “Hamiltonian means to achieve Jeffersonian ends,” or the hammer of centralized authority in service of universal freedom and opportunity.

The Architecture of Urbanity and the Moral Imagination of Design

That’s why Chakrabarti’s book is so refreshing. He doesn’t just theorize; he builds. Literally. His projects tackle climate collapse, xenophobia, war, and inequality. He offers not just design, but an ethic. One rooted in the belief that public infrastructure—mass transit, public housing, green space—is the social glue that holds diverse cities together.

And he doesn’t shy away from the political tension this work requires. As he puts it: “Rare is the leader who takes the risk of pointing it out when [community push-back] is wrong.”

That line stuck with me because the failure to build—housing, infrastructure, trust—often lies not in technical barriers, but in our political fear of making trade-offs, of offending, or acting. Sometimes, the loudest voices in a room don’t speak for the majority. And while we must always listen—especially when people raise concerns about safety, livability, or displacement—we also have to be brave enough to distinguish between resistance that protects the community and resistance that stalls progress for everyone.

The truth is that cities must grow or they calcify. If we want a Portland that’s alive, inclusive, and dynamic, we have to be willing to make some tradeoffs.

We Are Not Losers or Winners—We Are a Public

And that brings me to the the question that is top of mind for many Portland residents right now: how will the revaluation impact me? Last night during public comment, someone described the revaluation rollout in stark terms: if your property value increased above the 30th percentile, you’re a “loser” because your taxes will go up; if it increased less, you’re a “winner.” That framing misses something essential.

If your home value increased, it means your investment in Portland has grown. Yes, your tax bill may go up, but so has the value of your asset. And those tax dollars fund the infrastructure and services we all rely on and that allow us to grow: schools, roads, housing safety, emergency response. That’s not a loss—it’s a contribution to the public good.

We cannot solve our biggest problems through individual calculation alone. We need to move away from zero-sum thinking and think and act like a public. Because we’re not competitors in a game of winners and losers. We are co-investors in a city we share. The more we embrace that, the better chance we have of shaping a Portland that works—for all of us.


    ksykes@portlandmaine.gov 207-558-5764

    Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

    The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

    Friday May 30, 2025

    ONE BIG THING: Understanding Your Property Revaluation Notice

    Many of you have received your new property assessment from the City and are understandably concerned. I’ve heard from constituents whose property values have gone up significantly, and they’re worried that this means their taxes will skyrocket.

    Let me explain what’s actually happening.

    When the city revalues all properties, it resets the estimated market value of every parcel of land in Portland. This year’s revaluation increased property values across the city to reflect current market conditions, but the overall amount of money the City needs to raise through property taxes doesn’t change because of revaluation. Instead, the mill rate (the tax per $1,000 of value) is adjusted downward, and what changes is how that burden is divided among property owners.

    Here’s an example:

    • Before revaluation: Your home was valued at $350,000 and the mill rate was $20 per $1,000.
      → Your tax bill was $7,000.
    • After revaluation: Your home is now valued at $500,000—but the new citywide mill rate drops to $14.
      → Your tax bill is still $7,000.

    This means that even though your assessed value went up, your tax bill might stay the same—or even go down—depending on how your home’s increase compares to the citywide average.

    If your property went up less than the citywide average, your taxes could go down. If it went up more than average, they could go up—but not necessarily by the same percentage. We won’t know final tax bills until the new mill rate is set in August, after the City Council passes the FY26 budget.

    I want to be clear that I’m committed to tax fairness and balancing the city budget—but not on the backs of working families, seniors, and people living paycheck to paycheck.

    That’s why I’m working to:

    • Expand Portland’s Senior Tax Equity Program (P-STEP) to more residents, regardless of age.
    • Launch a PILOT program asking large nonprofits to contribute their fair share.
    • Strengthen financial oversight of city spending to ensure transparency and accountability.

    I’ll be advocating for these ideas in the Finance Committee. In the meantime, if you have questions about your revaluation notice, you can contact Tyler Technologies at 1-844-651-3398 or visit tylertech.com/portland.


    ksykes@portlandmaine.gov 207-558-5764

    Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.

    The District Five Insider is a newsletter about the big decisions making their way through the City Council, what they mean for District Five, and how you can get involved. Enter your email and click subscribe to receive this newsletter in your mailbox.

    Wednesday May 21, 2025

    ONE BIG THING: Shaping UNE’s Growth in District 5

    This week, the Council approved the University of New England Institutional Overlay Zone (IOZ), granting UNE long-term development rights over more than 70 acres in the Deering neighborhood. The zone creates a cohesive plan for UNE’s Portland campus and opens the door for projects like student housing for the medical school, transforming what has long been a commuter campus into a vibrant residential hub. It ensures that future development happens within a shared vision, not parcel by parcel.

    Councilor Bullett and I also introduced an amendment—passed unanimously—to expand environmental protections along Capisic Brook, permanently safeguarding water quality and green space in one of Portland’s most climate-vulnerable watersheds.

    At the same meeting, I introduced a resolution urging the Council’s Finance Committee to finalize a long-overdue PILOT (Payment in Lieu of Taxes) policy to address the growing footprint of Portland’s tax-exempt institutions.


    Why It Matters

    The UNE IOZ marks the third major zoning entitlement on tax-exempt land in recent years, following approvals for MaineHealth and the Roux Institute. These institutions now occupy vast sections of the city but are exempt from paying property taxes toward the infrastructure and services that sustain them. They benefit from zoning approvals, public infrastructure, emergency response, and long-term planning, but the cost is shifted onto working people, renters, and small businesses.

    According to the City Assessor’s Office, approximately $3 billion in Portland property is currently tax-exempt, representing over 20% of the City’s potential tax base.

    Meanwhile, property taxes are climbing. School budgets are growing. State reimbursements are uncertain. We are asking more from Portlanders while allowing some of the city’s largest landholders to grow without giving back.

    A PILOT program offers another way, one that treats growth as a shared civic responsibility. It’s a model where prosperity is reinvested in the communities that make it possible, and it works in other cities.

    Boston’s PILOT program generates over $30 million annually, using a fair formula based on property value and municipal service use, with credits for real community benefit. Portland has drafted a similar framework, but has yet to enact it.

    It’s time to move forward with a model that matches our values and invests in our shared future.

    Four Quick Hits

    • School Budget Passed: We protected vital school programming under fiscal pressure. A win for stability and equity.
    • Brighton Ave RFP Approved: The Council advanced affordable housing on city-owned land near the Barron Center. The debate, whether to prioritize family or elder housing, revealed how austerity forces us to choose between needs. I look forward to exploring new tools to build public equity in housing through the Social Housing task force so we can build housing for everyone.
    • Cannabis Loopholes Fixed: Retailers can now prepare non-alcoholic beverages onsite. A simple change that helps small businesses thrive on equal terms.
    • Minimum Wage Ballot Initiative Moves Forward: The Housing & Economic Development Committee approved a ballot measure that would finally include City workers, ending their exclusion from the 2020 wage hike and taking a stand for wage equity across sectors.

    What Comes Next

    The minimum wage initiative is a step toward fairness. But already, we’re seeing calls to carve out nonprofit employers, a move that would recreate the very inequity we’re trying to correct.

    Let’s be clear: under that amendment, someone washing dishes in a non-profit senior home could be paid less than someone doing the same job in a restaurant—same work, same hours, less pay—just because of who signs the paycheck.

    This is the logic of austerity: divide workers by sector, business size, or job title, and ask them to fight over what’s left.

    But we know another way.

    We can build a city where no one is carved out. Where wages are dignified, housing is abundant, and growth is shared. The work continues, and we’ll keep doing it together.


    ksykes@portlandmaine.gov 207-558-5764

    Notice: Under Maine law, documents – including e-mails and text messages – in the possession of public officials or city employees about government business may be classified as public records. There are very few exceptions. As a result, please be advised that what is written in a text message or e-mail could be released to the public and/or the media if requested.