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, September 25 2025

ONE BIG THING

Politics can be all-consuming.

For many people right now, the political arena has become the place where all of our feelings get expressed. The frustration, the anxiety, the sense that something is out of balance all gets poured into politics.

And with constant media and social media at our fingertips, it’s easy to fall into the trap of thinking that politics is the only place where change happens. But the truth is, most things cannot be solved in that space.

Our city ordinances, state laws, and federal statutes can’t heal what is spiritual, emotional, or psychological in nature. They can’t restore meaning or calm or clarity. These are things we have to find for ourselves, through quiet reflection, creative pursuits, and in community with others.

So this week, I want to share something that has nothing to do with the City Council. This week’s Big Thing is about pepperoni.

It’s the end of the growing season, and if you have a garden, you probably have a few tomatoes on the vine that will never ripen. They’re small, firm, and easy to overlook or toss in the compost. Please don’t!

Last year, I fermented some green tomatoes as an experiment, put them in the fridge and then promptly forgot about them. Around about February, I sliced a few onto a pizza because I didn’t have much else on hand and realized, to my surprise, that they taste just like pepperoni. As a vegetarian who is still nostalgic for the salty-sour-spicy flavor of a classic pepperoni slice, this discovery was a revelation. Here’s how to make them:

Fermented Green Tomatoes for Pizza (Vegetarian “Pepperoni”)

Ingredients:

  • Whole Green tomatoes
  • Garlic cloves (2–3)
  • 1 tsp black peppercorns
  • ½ tsp red pepper flakes (adjust to taste)
  • 2 tbsp salt
  • 1 quart water

Instructions:

  1. Pack your tomatoes into a clean glass jar with garlic, peppercorns, and red pepper flakes.
  2. Dissolve the salt in water to make your brine.
  3. Pour the brine over the tomatoes until they’re fully submerged. Push them down and wedge them against the jar to keep them under the surface.
  4. Cover loosely and let ferment at room temperature for 5–10 days. Taste every few days.
  5. Once tangy and flavorful, move the jar to the fridge.

Top a pizza with a few slices of these, sprinkle some smoked paprika over the top, and you’ll have something rich, spicy, and satisfying—no meat required.

In fermentation, the flavors develop over time, and so does the bio-availability of the nutrients in the food. The process happens slowly, naturally, when the conditions are right. With the days getting shorter and the nights colder, this is a season for doing the same. Turning inward. Slowing down. Letting things settle and change in their own time.

We’re all carrying a lot. The world feels heavy, fast, and unpredictable. But underneath that, there’s still something steady. Something waiting to change and to take a new shape, if we give it time. Autumn is a season of both creation and ending. The leaves that fall are returning their energy to the soil; the trees are pulling nutrients back into their roots; the bulbs of spring flowers are quietly storing up strength for their big reveal. Fermentation reminds us that these forces are not separate. What is breaking down can also be what is being born.

We don’t have to fix everything right now. We don’t have to be constantly reacting.

We can just be here, alive and present in the world, paying attention to what’s growing, even if we can’t quite see it yet.

Let that be enough for today.

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, September 16 2025

Breaking: City of Portland Submits Plan to Use 166 Riverside as Winter Emergency Warming Shelter

Late last week, the City of Portland submitted a grant application to MaineHousing that will shape the City’s emergency response to homelessness this winter. The application proposes to use 166 Riverside Industrial Parkway as the site for this winter’s emergency warming shelter, with a capacity of up to 60 individuals. The shelter would be open overnight during extreme cold weather only, activated when the daily low temperature reaches 15 °F or below, or snow accumulation of more than 10 inches occurs. It would operate from 7:30 pm to 6:00 am, with city staff on-site, and transportation provided via shuttle bus from the peninsula.

This decision will have sweeping consequences for residents, local businesses, and the most vulnerable people in our community. 

As the District 5 Councilor, I want to be clear that I do not condone this plan. It is deeply flawed. It’s a last-resort measure driven not by thoughtful strategy, but by sheer necessity. It reflects a breakdown of systems far beyond the City’s control, and it underscores how urgently we need action at the state and county levels.

An Operational Decision—Not a Council Vote

This plan was not voted on by the Portland City Council, nor was it discussed in any public committee meeting. The decision to apply for the grant and designate 166 Riverside as the warming shelter site was made by City staff, under the authority of the City Manager’s office.

Under Portland’s Council-Manager system, many day-to-day operational decisions, especially those related to grant applications, emergency shelter operations, and city facility use, are made administratively. Councilors are often informed after the fact, especially when timelines are tight. That was the case here: the grant application was submitted on Friday to meet a deadline, and Councilors were notified shortly afterward.

I am sharing this information now because I believe residents deserve to know what’s happening and why.

A Broken System Leads To A Broken Response

City staff have spent nearly a year trying to find a more suitable location for this winter’s emergency shelter. They explored every avenue: outreach to private property owners, appeals to local churches and faith organizations, and conversations with nonprofits and service providers. All declined to take on this responsibility.

That is not a moral or professional failure. The reality is that the people this shelter is intended to serve require care and supervision far beyond what any church basement or volunteer-led space can provide. Many are in active substance use, in severe mental health crises, or have been chronically unsheltered for years. No amount of goodwill can substitute for the medical and behavioral health infrastructure needed to intervene.

What this situation reveals is not a failure of compassion; it is a failure of capacity. And Portland cannot solve it alone.

Why This Site Is Problematic

Unlike last year’s downtown warming shelter at First Parish Church, this year’s proposed site is far off-peninsula, located in an industrial area without access to services, social networks, or foot traffic. The building at 166 Riverside, a retrofitted warehouse, is already operating as a shelter for asylum-seeking single men.

The City’s plan calls for partitioning the shelter to house two distinct groups:

  • Recently arrived immigrants, often fleeing trauma but generally in stable condition
  • And individuals with extremely high needs, including active drug use and severe behavioral health crises.

This is an extraordinarily difficult environment to manage, even with trained city staff on-site. City staff hope to serve both populations in separate spaces, but it raises concerns about the safety and stability of both populations, and about whether either group will get the support they need.

Who Will Actually Use This Shelter?

Based on last year’s experience, only about 10% of those who sought shelter on cold nights would be able to use 166 Riverside. These are individuals who may be newly displaced, temporarily un-housed for a night or two, but otherwise able to board a shuttle bus and comply with shelter rules.

The other 90% are the hardest to reach and the most vulnerable:

  • They are in active addiction and may not be willing or able to follow shelter rules.
  • They may be experiencing mental health episodes, paranoid or disoriented.
  • They often refuse to leave their belongings—shopping carts, bikes, bags of personal survival gear—on the peninsula.
  • They may not even perceive the shelter as a safe place.

Last year, even when shelter was available downtown, many left in the middle of the night—sometimes inadequately clothed in dangerously low temperatures—to go outside and use. They could not tolerate the indoor environment, even with peer support and counseling available.

Now imagine this happening miles from the city center, in a residential neighborhood.

The County and State Must Act

This is not a City of Portland failure. This is a failure of a statewide system that has refused to acknowledge the depth of this crisis for decades.

At the County Level:

  • Portland residents and businesses contribute millions each year to the Cumberland County budget.
  • For years, Portland has allowed our voting seats on the County Finance Committee to sit empty.
  • The Sheriff’s Department has not stepped up to offer the kind of medical or recovery-based intervention that other counties have implemented.
  • There is no sobering center, no detox facility, no jail-based treatment pipeline.

We need county-level infrastructure. And we need it now.

At the State Level:

Governor Janet Mills is sitting on a $1 billion rainy-day fund while Maine’s largest city, and its primary economic engine, is scrambling for short-term grant dollars just to keep people alive this winter.

Portland’s downtown—home to small businesses, vital services, and thousands of workers—has become the default safety net for the state’s most vulnerable residents. Our sidewalks and public spaces are not designed to function as an emergency shelter system, yet that’s what they have become.

Our city’s businesses are being pushed to the breaking point. They are showing compassion, hiring locally, and staying open, but it’s hard to operate when your storefront becomes someone’s last refuge from the cold. These businesses deserve support. So do the people who are sleeping outside their doors.

The Maine Legislature must take emergency action now to:

  • Develop a statewide emergency housing plan for winter 2025 that does not rely on municipal patchwork and last-minute scrambling.
  • Fund low-barrier treatment facilities for people with severe addiction,
  • Stand up stabilization shelters for those in acute mental health crisis,
  • Tap the Governor’s billion dollar rainy-day-fund to address this emergency.

I’ll say this plainly: I am beyond asking politely. This is a public health emergency that demands a FEMA-scale response, not municipal triage. If a fire or flood had displaced this many Mainers, we would not tolerate bureaucratic delays or jurisdictional finger-pointing. This is no different. The winter is coming. People will die. We need an emergency response to match the scale of the emergency.

It’s Time to Stand Together And Demand More

We’re doing everything we can at the city level, but we’ve reached the end of our toolbox, and our budget.

Portland cannot do this alone. We cannot be the shelter system, the detox system, the mental health system, and the refugee resettlement system for the entire state. And yet, we try, every single day, with fewer resources than we need, and more need than we can carry.

I know Riverton residents will be upset. They already voiced concerns when this facility was opened to asylum seekers. I expect the opposition will only intensify with this announcement. We need everyone—neighbors, businesses, advocates, and elected officials—to lift your voices where it can make a difference: the State House, the County Commission, and the Governor’s office.

This is your moment. If you’ve ever said, “Why aren’t we doing more?” — here’s your answer. And here’s your assignment: 

  • Email the County Commissioners and Sheriff. Demand that they step up and take action now to protect public health this winter.
  • Call your State Representatives and Senators. Demand a comprehensive response to homelessness and behavioral health crises.
  • Contact Governor Mills. Ask why she’s hoarding a $1 billion surplus while people freeze to death in Portland.

Temporary Shelter Is Not a Solution, It’s a Band-aid

This plan is a stopgap. It will not solve anything. It will not reach most of the people who need help. It will not prevent winter deaths.

What we need are long-term investments in treatment, housing, and care. We need leadership from people with the power to act, not just from those of us trying to patch the system from below.

This is where we are. And unless we fight like hell to change the trajectory, it’s where we’ll be next winter too. And the one after that, and the one after that… I am asking Portland citizens to stand up and demand change, demand that our county, state and federal partners do their duty.

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 12 2025

ONE BIG THING: Sharing the Responsibility for Portland’s Future

Last night, the Finance Committee had two big conversations about how we pay for City services: the Portland Senior Tax Equity Program (P-STEP) and the Payment in Lieu of Taxes (PILOT) Program. Both are about making sure the responsibility for funding our City is spread fairly, so that no one group is left carrying more than its share.

What Happened

The P-STEP Program was created in 2017 to help seniors—both renters and homeowners—who were struggling to keep up with rising housing costs tied to property taxes. The program was designed this way because state law recognizes that whether you rent or own, property taxes affect your housing costs. What many people don’t realize is that the state law enabling this program allows municipalities to design it for seniors, but does not require it to be limited by age. In other words, Portland could choose to expand this type of relief to younger residents as well. In the last couple of years, P-STEP has reached more households than ever, which tells us the need is growing. That success raises a bigger question: should this kind of relief be available to younger families too? After all, the rising cost of housing isn’t just affecting seniors.

We also discussed a revised draft framework for two approaches: a voluntary PILOT Program, and a municipal service charge. The service charge is authorized under state law (Title 36, section 508) and applies only to a narrow category of tax-exempt properties—those that generate rental income, but are otherwise exempt from property taxes. The law has been on the books since the 1970s, but Portland has not previously used it. It is mandatory rather than voluntary, but because it applies to a much smaller pool of properties, it would not replace a broader PILOT framework. Instead, Portland could use the service charge in conjunction with PILOT, ensuring that nonprofits benefiting from rental income, along with larger institutions like hospitals and universities, all contribute something toward the City services they rely on.

Why It Matters

Think about two neighbors on the same street. One is a retired senior who depends on a fixed income, and the other is a young family with kids in school. Both are facing rising costs, and both need the same services: safe roads, reliable emergency response, and schools that prepare the next generation. Expanding P-STEP to all ages would mean that both of those households could get help shouldering the cost of staying in their homes.

Or take another example: when a fire truck rolls out of the station, it doesn’t stop to check whether the property it’s headed to is taxable. Hospitals, colleges, and large nonprofits get the same protection and use the same infrastructure as everyone else. A PILOT Program would mean they contribute a small share back into the system that keeps their doors open and their staff and patients safe.

These aren’t abstract policy debates; they’re about whether Portlanders—young or old, homeowner or nonprofit—are all pitching in together to keep our community strong.

What Comes Next

The Finance Committee will keep working on both proposals this fall. No decisions have been made yet, but these conversations are setting the stage for policy changes that could have a real impact on households across the city.

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, 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.