Sitkans will elect two Assembly members, three School Board members and a new mayor in Tuesday's municipal election, and weigh in on the Assembly’s special election discretion.
Early voting is underway at Centennial Hall, with more than 450 ballots cast to far. To help voters make informed decisions, the Sentinel is collaborating with Raven Radio to publish responses from each candidate on questions regarding their backgrounds and views on key city issues.
Assembly candidates’ answers are below. Forums with mayoral candidates will be published Friday; School Board candidates appeared in the Sentinel Wednesday.
Four people are running for two seats in the Assembly race. Candidates are Sherri Blankenship, Darrell Windsor and incumbent JJ Carlson. Mary Ann Hall is an official write-in candidate.
Darrell Windsor
Windsor, 67, has lived in Sitka for 32 years. He's an appliance repairman, and owner of Sitka Appliance Repair. His son, daughter-in-law and granddaughter live in Sitka.
He has served on the Planning Commission for 15 years and is a member of the Masons.
When he filed in August, Windsor told the Sentinel that his goal in running for Assembly is to “try to make Sitka better any way I can.”
“I think I’m level headed, I think I look at both sides and come up with a conclusion,” he told the Sentinel just after he filed. “I’m not lopsided - heavy one way or the other.”
Sherri Blankenship
Blankenship, 46, was born in Dutch Harbor and has lived in Sitka for 23 years. She's owner of Highliner Coffee Co. She has raised her four children through the Sitka School District, and her husband lives here.
Blankenship currently serves on the Sitka Chamber of Commerce board, the Chamber Foundation board, and has served on the Safeguard Sitka committee. She previously ran for Assembly in 2025.
When she filed to run in August, Blankenship told the Sentinel that “I want to serve on the Assembly because I believe in thoughtful leadership, practical solutions and building a stronger future for Sitka."
“I’m committed to supporting our local economy. protecting what makes our community special and making responsible decisions that benefit residents today and for generations to come," she said.
JJ Carlson
Carlson, 40, was born and raised in Sitka. She left for college and to start her career, and moved back to Sitka six years ago. She works in nonprofit management, including Friends of SJM (Sheldon Jackson Museum). She has been an Assembly member since late 2022.
Carlson currently serves on the Sitka Community Health Council, an advisory body to SEARHC, and is a community volunteer and advocate with various public health initiatives.
In filing for her second term on the Assembly, Carlson said she wants to continue the work she's been doing, and focus on improving quality of life.
“There are several things in progress,” she said in August. “The strategic plan has outlined a path I’d like to continue working on: infrastructure, improved communication, quality of life and affordability to Sitkans.”
Mary Ann Hall
Hall has lived in Sitka for 31 years. She came to Sitka in 1959 after serving in the U.S. Navy Hospital Corps in Portsmouth, Virginia.
She currently serves with the Sitka Homeless Coalition; is in her sixth year of service on the Local Emergency Planning Commission; and previously served on the Health Advisory Council for SEARHC.
On her decision to run for an Assembly seat, Hall told the Sentinel in August that "I wanted to do something for my community because I love it. ... I want to try and help to have a good community."
Questions from Raven Radio:
1. Child Care Shortage -- A recent report commissioned by the city shows Sitka’s child care system has the capacity to serve only about half of the young children who need it. The assembly is considering a seasonal sales tax change to fund a $1 million-a-year plan to help address the child care shortage. Do you agree with this approach? What further steps, if any, should the city take to address the crisis?
Windsor: I do not believe in any new taxes until some cuts are involved.
Carlson: A seasonal sales tax is one of the few ideas the Assembly is considering as a funding mechanism to support child care in Sitka. The first Assembly meeting in September OCTOBER??
is scheduled to include a discussion on the next steps for what municipally-supported child care could be.
Blankenship: I absolutely believe Sitka needs to invest in a comprehensive and sustainable child care system. Where I am conflicted is how we fund it.
Sitkans have continuously been clear about the high cost of living here, and I am hesitant to add another cost to residents through an increased sales tax before we have fully explored other funding opportunities.
I believe we should first bring the private sector and some of Sitka’s largest organizations to the table. Many of these organizations employ significant workforces that depend heavily on our limited child care system, and they should be invited to become meaningful partners in the solution. I would like to explore private sector funding partnerships and then aggressively pursue state and federal funding opportunities that could match or leverage those local investments.
Child care is workforce infrastructure. A strong child care system benefits our employers, our economy and our entire community. I support investing in it, but before asking Sitka residents to pay more, I want to know we have done everything possible to build a broader funding partnership and bring outside dollars into the solution.
2. Budget -- How do you propose funding city government (including enterprise funds, electricity, water, etc.)?
Windsor: I think the tax structure in place now will work for funding the city. I believe we have to go over the whole budget line by line, which I have to admit I haven’t done so in the past, but will definitely in the future.
Carlson: Property and sales tax are the main mechanisms that fund our city government. Excise taxes could be utilized more. Property tax go to schools, and sales tax funds the rest of the general-purpose municipal responsibilities (streets, planning, fire, police, library, parks and rec, etc.). Utilities and specially services (electricity, water, wastewater, garbage, airport, harbors, etc.) pay for themselves through fees for the service. These are handled differently because they are not typically provided by the municipal government. All that background sets up the opinion that a solid one-year budget is the immediate result of a good 5-to-10+ year plan. The best thing we can do for prudent financial management is strong long-term planning and fiscal modeling.
Blankenship: I believe city government has to be funded responsibly, but affordability has to be part of every budget conversation. Sitka residents and businesses are already carrying a high cost of living, and increasing rates, fees or taxes cannot continually be our first solution when costs rise.
We need strong, long-term financial planning, careful review of spending and better prioritization of the infrastructure and services we already have. For our enterprise funds, we need to look individually at what it actually costs to operate and maintain each system, plan for future capital needs, and work toward keeping those systems financially sustainable.
But responsible budgeting cannot only be about cutting costs or finding new ways to collect more from residents. We also need to grow the revenue side of the equation. I want Sitka to actively pursue projects, partnerships and economic opportunities that bring new money into our community and expand our economic base. That includes supporting and strengthening the industries we already have while being open to new industries and opportunities that make sense for Sitka.
I also believe we should be much more aggressive about pursuing state and federal funding, grants and public private partnerships for eligible projects. We should be looking for opportunities where outside investment can help us build infrastructure, create economic activity and strengthen City revenues over the long term.
Before asking Sitkans to pay more, I want us asking whether we are spending wisely, pursuing every reasonable outside funding opportunity, and doing enough to create new sources of economic activity and revenue for our community.
3. Schools -- Do you support funding the Sitka School District to the maximum allowed by state law (a.k.a. the “cap”)? Why or why not?
Windsor: Yes, our schools are one of the top priorities. The city should support the schools any way it can
Carlson: Yes. Education is highly valued by Sitkans. Quality schools for their kids is one of few things a working family does not need to stress about in Sitka. The cost of living is burdensome for families here. Maintaining a high-preforming school system is imperative for retention of school-age families in Sitka.
Blankenship: Yes. I support funding the Sitka School District to the maximum allowed by state law.
I believe education is paramount to a healthy community. Strong schools contribute not only to academic success, but to the overall wellness of our children, families and community. They create opportunity, stability and connection, and they are an investment in Sitka’s future.
This also connects directly to our concerns about population and retaining younger families. If we want families to choose Sitka as the place where they build their lives, we need to demonstrate that educating and supporting their children is one of our highest priorities.
I recognize that maximizing school funding requires difficult choices within the City budget, particularly when resources are limited. But education is an area where I believe we need to prioritize our investment. Our children deserve strong schools, excellent educators and meaningful educational opportunities, and I support funding that commitment to the maximum allowed.
4. Affordability -- Affording daily life in Sitka is difficult for many, between rising fuel and grocery costs and housing and child care shortages. According to a 2024 report by the Alaska Department of Labor and Workforce Development, Southeast Alaska’s overall population is projected to drop by about 17% by 2050 — or roughly 12,000 people. That’s about the populations of Sitka and Wrangell combined. As an assembly member, how would you work to address affordability for Sitkans?
Windsor: First, try to lower cost of housing, and utilities. Housing is a tough one, but the city can help with land policy. And a good long look at utilities may come up some way to lower cost. Hard to pinpoint without budget right in front of me on the utilities.
Carlson: The CBS strategic plan lays out a quality and targeted approach to addressing affordability challenges for Sitkans identifying housing, utility costs, child care, and food security as action items. The Assembly annually reviews utilities costs and is actively working on housing and child care. ADU code refinements will be voted on within the next few months, and a child care solution is progressing in development. I will continue to address affordability for Sitkans with steady, collaborative, and creative problem-solving.
Blankenship: Affordability is one of the biggest challenges facing Sitka, and I don’t believe there is one policy that will solve it. We need to look at the cumulative cost of living here and recognize that every increase in taxes, utility rates, fees, housing and child care adds to what families and individuals are already carrying.
As an Assembly member, I would be cautious about adding new costs to residents without first exploring other options. That means responsible budgeting, aggressively pursuing state and federal funding, developing private sector partnerships where appropriate, and looking for projects and economic opportunities that bring new revenue into Sitka rather than continually relying on the same taxpayers.
Housing and child care are significant pieces of affordability, and both require us to move from repeatedly discussing the problems toward implementing solutions. With child care specifically, I believe some of our largest employers and organizations need to become active partners in funding and strengthening the system their workforces depend on.
I also think affordability and population decline are directly connected. We can talk about attracting and retaining younger people and families, but if they cannot afford to build a life here, we will continue to lose them. Addressing that requires more than lowering one particular cost. It means strengthening our economy, creating good jobs and educational opportunities, supporting local businesses, expanding housing opportunities and building the support systems that allow people to stay.
The goal should not simply be making Sitka less expensive. It should be making it more possible for people to build a sustainable life here.
5. Tourism -- The commercial passenger vessel excise tax – also known as the CPV – is a “head tax” collected by the state and distributed to port cities. The funds are highly restricted, and can go only toward harbor or other infrastructure related to services or facilities used by cruise ships and their passengers. As an Assembly member, how would you prioritize spending CPV money, considering the restrictions?
Windsor: First, look for problems in the harbor and infrastructure, prioritize the list and start working at solving them.
Carlson: Utilizing interest on the CPV special revenue fund is a viable avenue of exploration. After annual CBS operational expenses are covered (per the existing formula), capital project prioritization happens annually as part of the capital improvement program. I currently, and will continue to, prioritize spending CPV money on projects that meet the stipulated needs of visitors while addressing quality of life concerns for locals.
Blankenship: I believe the restrictions surrounding CPV funding deserve to be revisited. The impacts of cruise tourism on a community extend beyond a narrow definition of port infrastructure, and I would support advocating at both the state and federal level for greater flexibility in how communities impacted by cruise tourism can use those revenues.
Until those rules change, however, we have to work responsibly within the guidelines we have.
I would prioritize projects that have already been identified and discussed by the community, while also developing a clear list of eligible needs based on urgency, community benefit and how long those needs have gone unaddressed. I don’t think we should create projects simply because CPV money is available. The funding should be directed toward projects we actually need and that provide long term value to Sitka.
We also have to recognize that many major infrastructure projects will cost considerably more than the CPV funds available. That means looking strategically at how CPV dollars can be combined with grants, state or federal funding and other eligible funding sources to accomplish larger projects without unnecessarily placing the remaining cost on Sitka residents.
These funding programs can be restrictive and often move slowly, so good planning matters. If we establish our priorities ahead of time and have projects ready, we are in a much stronger position to pursue and leverage additional funding opportunities when they become available.
6. Tourism -- The city has expanded its tourism management in recent years, adding a tourism commission and hiring on a new tourism director in response to growth in the sector. From your perspective, what should be the city’s role in tourism moving forward?
Windsor: Infrastructure, such as adding rest facilities and such.
Carlson: CBS has taken great steps so far in managing cruise tourism. Thank you everyone for your patience and understanding as we grew in knowledge and capacity to meet the current levels. As an Assembly sponsor of many of the recent tourism management initiatives, your feedback and participation was invaluable in crafting our current response to the increase of cruise visitation. Going forward, the city must consistently reiterate to the cruise lines – and actively review for right-sizing – Sitka’s preferences of a 7,000 daily passenger limit, designated quiet days, and a shorter season. Sitka has long been a desirable destination by the independent traveler. Moving forward, we need to re-focus on increasing independent travel to Sitka in the shoulder season.
Blankenship: I believe the City’s role should be to support a strong and sustainable tourism economy while making sure the industry continues to benefit Sitka as a whole.
Tourism is an important economic driver for our community. It supports local businesses, creates jobs, generates City revenue and brings outside dollars into Sitka. I believe the City should recognize that value and work collaboratively with the businesses, organizations and industries that make our visitor economy successful.
Moving forward, I would like to see the City focus on strengthening those partnerships, supporting local businesses in capturing more of the economic benefit tourism brings, and making thoughtful investments in infrastructure and services that benefit both our visitor economy and our community.
As tourism continues to be an important part of Sitka’s economy, we should be looking for opportunities to make sure that economic activity translates into meaningful benefits for our local businesses and community.
At the same time, we need to continue listening to the community as a whole and be willing to make thoughtful adjustments along the way when needed. Tourism should work for Sitka economically while also maintaining a level of balance and comfort for the people who call Sitka home.
7. AI -- The use of artificial intelligence has proliferated over the past several years. It’s reshaping how people work, learn, and participate in daily life. What are your thoughts on using AI in your role as an assembly member or to write legislation?
Windsor: I think AI should only be used as a reference point. Not writing anything on its own.
Carlson: AI is a potential tool, but writing an ordinance is not where the bulk of the work is. Coordination, communication, and community feedback is the work of the Assembly member and AI is not directly applicable.
Blankenship: I believe AI has tremendous value when it is used appropriately, but it should be a tool, not a substitute for independent thought, personal research or human judgment.
As an Assembly member, I would use AI in much the same way I use other tools and resources. It can be helpful for comparative research, organizing large amounts of information, improving grammar and clarity, and helping create flow when communicating complicated ideas. But the information it provides still needs to be questioned, verified and understood.
Some of the most valuable knowledge we have comes from homegrown conversations, listening to people with direct experience, learning from past decisions and the wisdom of mentors, and building relationships with people who understand an issue from different perspectives. AI cannot replace that.
When it comes to legislation, I would be comfortable using AI as a research or organizational tool, but I would never rely on it solely to create policy. Legislation requires legal review, factual verification, public input and ultimately human accountability.
AI can make us more efficient and help us ask better questions, but the responsibility for the decisions we make should always remain with us.
8. Municipal Administrator -- The city has been looking for a new municipal administrator for about a year now. You would likely be part of that hiring decision. What qualities would you look for in a leader?
Windsor: Someone that has run a department or company in the past. Also, hopefully someone from Alaska.
Carlson: Leadership and management are different still sets; the CBS municipal administrator needs both to be successful. Prioritization and time management are key for effective and efficient workflows, while at the same time, an approachable demeanor and receptive listening are also a necessity. There are many of these seemingly opposite qualities that make for a strong leader. It provides balance and demonstrates a holistic approach that is often a product of experience and is transferable between subject matters.
Blankenship: I would look for someone who understands small communities, ideally through lived experience, and understands that managing a small municipality requires a different kind of leadership. I want someone who will genuinely integrate into Sitka, become invested in our community and understand the realities our families, businesses and residents experience every day. Someone who can meet people where they are.
A strong background in management and financial literacy would be very important to me. We need someone who understands budgets, people, operations and accountability, but who also recognizes that good leadership is about more than policies and procedures.
I would look for someone who understands that policy and structure are necessary, but they don’t replace common sense, compassion and good judgment. More government does not automatically mean better government, and more control does not necessarily create better outcomes.
I would also look closely at someone’s entire leadership history, including their failures. I don’t expect a great leader to have a perfect record. I would rather see someone who has faced difficult situations, made mistakes, learned from them and demonstrated a pattern of stronger decisions and success afterward.
Most importantly, I would look for someone with integrity, humility and the ability to listen. Sitka needs an administrator who can lead effectively while remembering that municipal government ultimately exists to serve the community.
Questions from the Daily Sitka Sentinel
1. A group in Sitka is laying the groundwork for new city recreation facilities, such as an upgraded track and field complex. How do you feel about developing new recreation infrastructure and expanding capacity for recreation in Sitka?
Hall: It’s okay with me.
Windsor: I think that new recreation facilities is a very good idea if it can be done cheap enough and open to everyone. If you don't own a boat in Sitka, your limits to recreation are very narrow – especially now that you have to pay to park at state parks, or federal campgrounds and parks.
Blankenship: I am absolutely supportive of expanding recreational infrastructure in Sitka. Creating more opportunities for recreation benefits our youth, families, and the community as a whole.
I also think it plays an important role in retaining and attracting younger people and families. If we want people to build their lives here, we need to continue investing in the quality of life that makes Sitka a great place to live and raise a family.
2. Do you think the city general fund is at a healthy level? How would you cut or add spending?
Hall: I don’t know what level the city general fund is at.
Windsor: I think the general fund seems to be in good shape. But not having the budget in front of me, not 100% sure on that. I do believe cuts should be made to the budget, but again, without the budget in front of me I can't say right now.
Blankenship: I think our General Fund is currently stable, but we need to be thoughtful about how we manage it moving forward. I would be cautious about adding new recurring expenses without identifying sustainable revenue to support them.
Rather than simply cutting services, I would look closely at where we can operate more efficiently and prioritize spending that directly benefits our community. I also think we need to be much more aggressive about leveraging grants, partnerships and private-sector participation before putting additional financial pressure on Sitka residents
3. What are your ideas for stemming the decline in Sitka’s population, particularly the loss of young families, and the associated decline in Sitka School District enrollment?.
Hall: Let the city build condominiums on city land and rent them to young families.
Windsor: Having thought a lot about this very problem, my conclusion is we will never be able to bring any form of industry that will support our city like the mill or SJ did. So instead of spinning our efforts in that direction, we should be working hard on improving what we have and try to narrow down spending to make living here more affordable.
Blankenship: I believe the loss of young families is one of the most important issues facing Sitka, and declining school enrollment is a symptom of that larger problem.
We need to make it possible for young people who grow up here, and young families who want to make Sitka their permanent home, to actually stay. That means attainable housing, accessible child care, strong schools, stable year-round jobs and career opportunities, and continuing to invest in the quality of life that makes people want to build their lives here.
There isn’t one solution. It will take the City, School District, businesses and our largest employers working together to address the barriers that are pushing young families out.
4. The city has long deferred a project of improvements along Lincoln Street. Should the city prioritize this project, and if so, what changes should be made along Lincoln Street?
Hall: (Did not respond)
Windsor: I think we have bigger issues with our infrastructure at this time, so no, I don't believe Lincoln Street should be number 1 on the priority list. We on the Planning Commission have looked at this in the past, and only came up with making Lincoln Street one way and slant parking. Any decision on this should be a vote of the public.
Blankenship: I voted yes on the Tourism Commission to prioritize the Lincoln Street project. It is long overdue, and our downtown is in desperate need of repair and rehabilitation. We need a vibrant, living downtown that our own residents are drawn to and that our visitors can enjoy as well.
There have been several ideas discussed about what the final Lincoln Street project could look like, but I don’t believe those discussions have progressed far enough yet to commit to a specific design without further public input.
What I can speak to are some of the issues that clearly need to be addressed. Our sidewalks need improvement and, where possible, should be slightly widened. The sidewalk edges also need to be safer and better defined. I have personally seen people step or slip off them, and I know both residents and visitors have experienced this.
Whatever the final design looks like, I want it to improve safety, accessibility and the overall appearance of downtown while preserving the character that makes Lincoln Street uniquely Sitka.
5. Do you believe that the city should keep Lincoln Street open to vehicle traffic throughout the summer cruise ship season, or close the street to vehicles on some days? Why?
Hall: Keep Lincoln Street open to vehicle traffic throughout the summer.
Windsor: Closing down Lincoln Street on the heaviest cruise ship days seems to work. Our existing sidewalks cannot handle the big heavy days.
Blankenship: Yes, I believe Lincoln Street should remain open to vehicle traffic throughout the summer. Our residents should continue to have access without unnecessary barriers to their own downtown area.
Keeping traffic moving also helps visitors disperse more naturally into the surrounding areas rather than concentrating everyone within the downtown core. That can help reduce congestion while also spreading the economic benefits of tourism to businesses beyond Lincoln Street.
I believe we can create a downtown that is safe and welcoming for pedestrians without limiting access for the people who live here.
6. How can the city provide adequate restroom facilities for tourists? Do you think the city should continue operating portable restrooms throughout the summer, and if so, where should the portable restrooms be placed?
Hall: Where they are now.
Windsor: I do not like portable restrooms, and especially closing down a road for one. The city should look into building a new restroom on the corner of Seward Square or in city hall.
Blankenship: Adequate public restrooms are absolutely necessary during our visitor season, but I don’t believe the current location is a good long-term solution. Closing a downtown access street for several months to accommodate temporary restrooms creates its own challenges, and the appearance of the facilities in the middle of our downtown is also something we should address.
For the immediate future, temporary restrooms may still be necessary, but I would like to see us seriously evaluate better locations and ultimately work toward permanent, well-designed public restrooms that serve both residents and visitors.
This is a need we know will continue year after year, and I think it is time to find a solution that functions better and fits more naturally into our downtown.
7. How do you see the role of public safety and policing in keeping our community safe?
Hall: Let’s have a residents day – no cruise ships.
Windsor: I think with our new police chief and police staff being brought up to par, our public safety is up to is very adequate.
Blankenship: This is a fairly broad question because public safety encompasses so many different responsibilities within our community.
I do believe we have made incredible improvements in public safety and policing over the last year, and I think it is important to recognize that progress. Continuing to adequately staff, train and support our police department while building strong relationships between officers and the community is incredibly important.
In a small community like Sitka, trust, communication and accountability between law enforcement and the people they serve are essential. I believe we should continue building on the progress we have made while making sure our officers have the resources and community support they need to keep Sitka safe.
