While Southold Town Hall was closed for a four-and-a-half-day Thanksgiving break, Supervisor Scott Russell labored not with pen and paper, but with spackle and spade. 

As a practical joke, Mr. Russell constructed a pseudo wall, sealing and disguising the doorway to his office. When his secretaries, Lauren Standish and Michelle Tomaszewski, arrived at work the following Monday, they were surely shocked by the latest and grandest of the supervisor’s myriad over-the-top efforts to make others — or at least himself — laugh. 

“We always joke you never know what you’re going to walk into on a Monday,” Ms. Standish said, reflecting on the roundabout route she and Ms. Tomaszewski took to their desks that morning. “We’ll miss him. He made us laugh all the time.”

The rather impractical joke stands in stark contrast to what Mr. Russell is most proud of during his 18 years as supervisor: an open-door policy. Be it a resident raising a private concern or a civic group requesting his attendance at a public meeting, Mr. Russell said in a recent interview that he took pride in “the fact that I was able to make someone else’s priority my priority, however big or small the issue seemed.

“Anybody can approach me at any time,” he added. “I might not be able to come through for them, but they know they can pick up the phone and call me — doesn’t matter whether you’re one of the laborers at the highway department, or [the Department of Public Works] or one of my department heads.”

Mr. Russell’s time in office was not all jokes. In many official meetings, he engaged in heated debates over pressing issues with members of the Town Board. This has been especially true with Councilman Greg Doroski, a frequent challenger to Mr. Russell’s positions and his opponent in the 2019 race for supervisor. Mr. Doroski previously told The Suffolk Times that in one particularly tense debate in a closed executive work session, he himself resorted to using strong language.

“When we walk out of the work session, we’re usually joking around with each other and talking,” Mr. Doroski said in a recent interview. “We can have a really, really fierce debate, walk outside and have a conversation. There have been times where Scott and I have had a [conversation] really kind of pushing the limits of what a debate should be. We step away, and he’ll shoot me a text after or I’ll shoot him a text and maybe walk it back a little bit and kind of reevaluate. And I think that’s good.”

A former assistant town attorney has also alleged that Mr. Russell violated the town’s workplace violence prevention and sexual harassment policies. Tuesday evening, the Town Board adopted the findings of an outside investigator which absolved the supervisor of these claims. However, the matter remains pending, as Mr. Hagan filed a complaint with the New York State Division of Human Rights.

Although he was always willing to engage with Town Hall personnel on any issues of concern, by his own admission Mr. Russell often struggled with delegating responsibilities during his first few terms. But when Superstorm Sandy struck in 2012, he leaned on the members of the town’s emergency response team and other essential town employees and volunteers.

“I learned that we have an excellent town, that we have fire departments that are there through thick and thin,” Mr. Russell said of the crisis, one of the biggest he faced during his tenure. “I learned that when it comes to events like that, everybody pulls together and works together … We were able to mobilize very quickly. The left hand knew what the right hand was doing. We all assumed a role. As difficult as that storm was … [our response] went smoothly. Everybody did their part.”

The day before Sandy struck, Mr. Russell issued a townwide evacuation order, a decision that he felt was best for the town. After the storm passed, the public agreed.

“I never heard so much as one complaint,” Mr. Russell said. “Based on the damage, in retrospect, it validated the order.”

As he ran for supervisor for a fifth time in 2019, Mr. Russell announced another tough decision he believed would be best for the town. He decided his next term would be his last. “We needed a fresh set of eyes,” Mr. Russell said.

At age 12, Mr. Russell’s family moved from Nassau County to Southold Town. After graduating from Mattituck High School in 1982, he attended George Washington University, where he majored in American studies and government. His first taste of politics came with an internship under former congressman William Carney, which evolved into a paid legislative aide position.

In 1990, while bouncing back and forth between working as a legal assistant for a New York City law firm and bartending in Southold on weekends, Mr. Russell was approached to run for town assessor. To his surprise, he won the election.

“I didn’t think I had a chance,” he said. “Ultimately, I was lucky.”

In retrospect, Mr. Russell’s 15 years as an assessor proved to be a key asset in his long-running political career.

“Being an assessor allows you to discuss individual properties with individual residents of town, so you get to know the properties and the people,” said Peter McGreevy, chairman of the Southold Town Republican Committee. “That is a great jumping-off point for moving into another elected office because you’re familiar with the town in detail, and you know a lot of the residents in detail.”

While working as an assessor, Mr. Russell said he fielded offers to run for other offices at the county and state level, but never pursued them. In 2005, he won his first of five successful bids for supervisor. “I didn’t want to spend half my week in Albany,” Mr. Russell said, explaining why he didn’t pursue a state or county position. “When I first ran for supervisor, my son was only 1, my daughter was 4 … I thoroughly enjoyed the town and I thoroughly enjoy being a dad, so I opted to stay in the supervisor’s post. I never planned on staying as long as I did. It just worked out that way. I enjoyed it thoroughly, every minute of it. I kept running for reelection because I always felt like there was a little bit more to do.

“I still feel like there’s more to do, but [the town] is in very capable hands,” he continued. “I think Albert Krupski will turn out to be the best supervisor this town has had in probably over a century. He’s one of the most decent people I know.”

During his nearly two decades in office, Mr. Russell helped raise two children, got divorced and lost both his mother and, in 2020, his longtime mentor and deputy supervisor, Bill Ruland. He said he managed his personal affairs “very poorly at the beginning,” but later learned to better handle the work-life balance.

The supervisor, now 59, also grappled with multiple health concerns during his Town Hall tenure, but said he “never let them interfere with the job,” a quality several of his colleagues admired.

“If he didn’t have all that, I think he would definitely be a congressman or a senator or something by now,” said Dennis Noncarrow, current Southold Town clerk and a former chair of the town Republican Committee. “A lot of times I’m amazed, he just shows up like nothing happened. He keeps going.” 

Among the legislative accomplishments Mr. Russell is most proud of are his efforts to preserve Plum Island and updates to the town’s comprehensive plan, which required more than a decade of work before it was adopted in 2020. 

In recent months, Mr. Russell has tried to rectify two of his legislative regrets regarding Airbnb rentals and affordable housing. He proposed that the town alter its code to increase the minimum number of days a property must be rented from 14 to 30. He also urged council members to consider reducing the number of affordable units allowed per acre within an Affordable Housing District from 12 to eight, a density he believes the public would be more likely to support. He believes these proposals are suited to tackling the town’s struggles with enforcing short-term rental codes and turning affordable housing proposals into realities. Without enough support from his fellow Town Board members, however, both initiatives stalled in work sessions.

Mr. Russell, a self-described “moderate Republican,” has often been commended by peers on both sides of the political aisle for his fiscal conservatism and management of town finances.

“I think over the past 18 years he’s been a very good manager of the town,” said Mr. Doroski, a Democrat. “He’s kept the budget really in line, and kept taxes low, and I think we should all be very grateful for that.” 

Perhaps above all else, Mr. Russell prides himself on his accessibility. To his colleagues and the public, he always maintained an open-door policy.

“Scott was always a candidate that would discuss any issue with any town resident,” Mr. McGreevy said.

Over the years, Mr. Russell formed relationships with countless people, but grew especially close to Ms. Standish and Ms. Tomaszewski. When they discussed Mr. Russell’s imminent departure, both commended his flexibility and said they considered him a good boss.

Even the supervisor’s penchant for pulling pranks, often at the expense of his secretaries, was not frivolous, but a way of lightening the heavy workload he and his team carried. Ms. Standish and Ms. Tomaszewski were often the first to hear from irate residents looking to speak with him. And on the few occasions they felt threatened as a result, they said, Mr. Russell not only intervened but de-escalated the situation. 

In the end, many of the supervisor’s peers label his tenure a success. But like any topic introduced in a Town Board work session, there is room for debate.

“When you look at what the town was when Scott came in and what the town is now, it still is one of the best places to live in the world,” Mr. Doroski said. “Scott has played a role in preserving this area and keeping it true to what it is. But … preserving the community is more than just preserving land or preserving the aesthetic feel of the place. I think we’ve struggled, and I think Scott has struggled as a leader of the town, to really figure out a way to preserve the people of our community so there’s not this brain drain of kids moving away.”

Although newcomers and second-home buyers are essential to Southold’s prosperity, the town’s exploding popularity has made it harder for many who grew up here to stay. Mr. Russell said he recognizes this and understands that it must be addressed not only by the town’s future administrations, but by the entire community.

“We all need to be cognizant of this growing chasm that’s getting worse,” Mr. Russell said.

With 33 years of service to Southold coming to a close, Mr. Russell looks ahead with an open mind.

“There are private opportunities that I’ve been discussing with people out west, people that are not even located in Suffolk County,” Mr. Russell said, noting that his children are grown, freeing him up to consider work outside the area.

While reflecting on his lifetime in public service, Mr. Russell said he does not believe in a legacy. Many of those who were asked to take stock of Mr. Russell’s tenure aired a common sentiment, which, if not a legacy, would certainly make a strong political epitaph should Mr. Russell step away from that arena permanently.

As Mr. Doroski put it, Mr. Russell has “given his life to this town.”