Leadership reveals itself in the hard moments. It is not enough to simply hold office or repeat talking points when things go wrong. A mayor is expected to step up, take responsibility, and help guide the town forward. But ideas alone do not lead. They have to be put into practice. That means having a clear understanding of what the town is, where it is headed, and how we plan to get there. For too long, we have lacked that kind of direction. Instead, we have been left with vague reassurances, shifting explanations, and policies that often contradict the very goals they claim to support. I want to take a moment to share just a few of the many examples from the last few years that show what happens when there is a vacuum in leadership.
When a leadership vacuum exists, the last line of defense becomes concerned residents who pay attention when bad ideas surface. We saw it with LIDs and, more recently, the proposal to ban RVs on private property. Both items quietly disappeared from the agenda after community pushback. Engaged citizens had to step in and fill the role the mayor should have played. Without that pushback, the council members who had been nodding along in agreement likely would have moved those policies forward.
When the mayor does not set boundaries or provide guidance to the Town Administrator, the administration pushes too far in its pursuit of revenue from the townspeople. Although seeking new revenue is part of the administrator’s job, without clear leadership the focus turns inward in alarming ways. The Town Administrator has raised property taxes as much as possible without a vote of the people and repeatedly calls for even higher levies. Fees on ratepayers have been eagerly increased, and the Town Council was quietly persuaded to rewrite the entire municipal code so that nearly every action involving private property now requires a permit fee. To show how far the administration is willing to go, an occupancy tax was floated that would have penalized people for not living full time in their homes. The idea was abandoned only after it was discovered to be illegal.
Across different issues, there is a pattern of poor communication and an unwillingness to meet residents where they are. Take the Lampard neighborhood. Several homeowners were blindsided when told they were solely responsible for connecting to the sewer main, despite decades-old infrastructure and unclear boundaries in the area. Those properties had always operated under a handshake agreement with the town that the town would eventually connect them. This kind of ambiguity exists throughout the town. Instead of working with residents, the town’s stance was essentially too bad, so sad. That is how it is now. This was not just poor communication. It showed a disregard for fairness, flexibility, and the town’s responsibility to work with residents in good faith.
Unlike the residents in the Lampard example, other town issues have resulted in lawsuits. Let us not forget the costly and unnecessary legal fight with San Juan County when the town claimed the County Fairgrounds was using water illegally. The county pushed back and took the town to court. In January 2025, the judge ruled that the town had acted beyond its authority, based on an error of law and without substantial evidence. The town lost. That was time, energy, and taxpayer money spent on a fight that never needed to happen.
More recently, the Holli Walk debacle has shown how the mayor’s role is being used to protect the administration, including allowing last-minute agenda changes and cutting off public comment to prevent discussion during a town council meeting. In the meantime, residents and the home trust remain in limbo. Quantifiable damage is being done to our neighbors by their own government. Both are bearing a real burden and facing failure.
In that thread, the Town Administrator took to social media. I was personally surprised to be shown a rambling, disjointed, defensive Facebook post about town business. Maybe it was written in a personal capacity, but when you are the top official in a public organization, there is no clear line between personal and official when commenting on town matters. Not everyone uses social media. Town business should always adhere to public disclosure. The mayor, and for that matter the council, are missing in action and struggling to get a handle on how this is communicated and resolved. I predict a lawsuit.
The same inconsistent judgment shows up when it comes to development. The difference in treatment is stark. When wealthy hoteliers come forward with plans, staff often recommends variances and clears the path. A clear example is the ongoing dispute between the American Legion and Friday Harbor House. Despite the Legion’s objections about blocked views, height violations, and long-standing property use, the town staff approved a hotel expansion. Now the Legion is suing the town. Another lawsuit with the same repeated patterns. If you have money and connections, the doors swing open. If you do not, prepare for red tape.
While there is plenty of room for it, I do not think the Friday Harbor House example is about corruption. Simply, a homeowner or nonprofit cannot afford a long legal battle. A well-connected developer can. The administration judges which fights are safer to pick and, in choosing these battles, creates double standards. On one hand, there is a firm stance that these are the new rules and everyone must adhere to them. Yet when it suits, the administration reverses course and recommends variances.
Last but far from least, in early 2025, contract negotiations between the Town Administrator and the employee union became increasingly strained. The process reportedly caused growing frustration among staff, who felt the administrator was handling the situation poorly. Employees were publicly protesting. The union accused her of negotiating in bad faith and eventually filed a formal complaint. At the same time these negotiations were still underway, the administrator went to the Town Council and successfully renegotiated her own contract, securing a substantial raise. The timing of that move, combined with the tension surrounding the union talks, dealt a serious blow to employee morale and created poor optics for the town.
According to watchdog websites and public records from the Town of Friday Harbor, in 2022, the Town Administrator held the highest-paid position in town government at $124,167 per year. By 2023, that salary rose sharply to $164,014 per year. As of 2025, the reported compensation is around $185,000 per year.
The Administrative Executive Assistant was listed in 2025 with an annual salary of approximately $88,000. Together, these two administrative roles now account for over $270,000 per year in compensation.
To be clear, there is no suggestion that the current administration lacks the talent to justify such compensation. In fact, one could argue the Town Administrator is underemployed. The disconnect is, having that level of administrative firepower in a town the size of Friday Harbor is like buying a bazooka to hunt bunnies.
These are just a few choice examples of many that show why the mayor matters. And while I have lost faith in our town government to the point where if all things stayed the same I would support disincorporation. I, however, have hope that maybe out of this large pool of mayoral candidates someone shall emerge that will effect change.
For the candidates I would like to know:
How will you set clear expectations for the Town Administrator and hold that position accountable to residents rather than the other way around?
What steps will you take to rebuild trust and morale among town employees?
How will you protect private property rights while keeping the cost of living and doing business within reach for working families?
In practical terms, how will you bring genuine public input into policy making before staff drafts ordinances or regulations?
Do you believe current administrative pay levels are appropriate for a town of this size, and if not, what changes will you pursue?
What criteria will you apply to ensure that all applicants, from homeowners to large developers, receive equal and consistent treatment under town rules?
If past administrative actions are found to have harmed residents or created double standards, will you commit to reviewing and, if necessary, reversing them?
Do you believe it is appropriate for town officials or staff to discuss or conduct town business on Facebook or other social media platforms?
Jeremy Nash
VOTE!
This letter reflects my perspective as a resident and voter. It is based on publicly available information and community conversations, and should be understood as opinion.