When it comes to anything related to development, few people have their finger on the pulse of Oak Harbor like Jim Woessner does.

The Oak Harbor native retired from the Oak Harbor City Council last month after deciding not to run for reelection last year. But while he’s leaving elected office behind and faces both devastating challenges and unique opportunities ahead, Woessner said he’s not done with trying to help improve the city and speaking his mind.

“History repeats itself if you don’t have someone like me,” he said with a laugh.

Spending a couple of hours with Woessner is like getting an in-depth city history lesson along with unique insights into current movers-and-shakers in the community. Rhonda Severns, former city employee and wife of former mayor Bob Severns, said it was this knowledge that led her to urge Woessner to run for city council more than eight years ago.

“If you want something done in this city, just call Jim Woessner,” she said.

As an astonishingly successful real estate agent — he said he was the No. 1 agent on the island six out of the last nine years — Woessner prides himself on his knowledge of the intricacies of land-use planning. As a council member, he said he focused on trying to improve the affordable housing crisis by working to institute city reforms that he hopes will help. Specifically, he said he worked to convince staff and other city leaders of the value of allowing accessory dwelling units. In addition, he said clarifying development code was an important step.

“It’s so frustrating for developers to walk into City Hall and get three different answers from three different people,” he said.

In fact, he sees reason for optimism.

“There is more construction going on in Oak Harbor now than in the last 10 years combined,” he said.

Woessner calls himself a “true native” of Oak Harbor, which is somewhat unique in an island community touched by the transient nature of the Navy base. His roots go back to great-grandparents who arrived in 1905 and settled in a farm near the Soundview Shopper on North Whidbey. His mother, Carol Oakley-Helde, was the director of the USO, which is where he spent much of his time growing up.

“The community really raised us as kids,” he said.

Woessner is a 1979 graduate of Oak Harbor High School. After a couple of years of college, he returned to Oak Harbor and has stayed put, becoming omnipresent in volunteer and development-related circles.

In addition to owning and running a Sears store, Woessner explained that he was involved in land development for many years. He said he was talked into becoming a real estate agent and worked part-time at first. Then fellow agent Craig McKenzie got the “bright idea” of starting a Homes for Heroes affiliate in Oak Harbor with the goal of “giving back” $1 million to those who serve, he said; it’s a goal that was far surpassed.

Woessner’s success in real estate is evident by the number of times he had to recuse himself from council decisions because he was involved transactions over the years. Most recently, he handled the city’s purchase of a former indoor shooting range as well as Island County’s purchase of property in downtown Oak Harbor.

Woessner is a longtime member of the Oak Harbor Rotary Club and past president of the North Whidbey Lions Club. He and McKenzie started the Hydros for Heroes fundraising event, and Woessner is the founder and voice for the annual Lions Club car show.

Tragedy struck when his wife succumbed to cancer in 2010, and he credits the community with getting him through the dark days. He said he spent “every cent” he owned trying to save her after her cancer diagnosis and also put off treatment of his own cancer. When she passed away, the community funded her funeral. Fifteen days later, he underwent the first of five cancer surgeries.

“Not only did the community step up and give her a proper funeral, they helped me with some bills,” he said.

His cancer has returned and is beyond treatment, he said, but he plans to stay active for as long as possible. According to his council biography, Woessner was fortunate to reconnect with another Oak Harbor native, Carol Pike-Vinson, after he was widowed. He said he’s working to set up his son and his family to take part in a documentary show about people who live off-grid in America.

Woessner said he’s been involved in the Rotary Club’s efforts to rebuild a windmill in Windjammer Park, and he hopes to reinvigorate the effort now that he’s no longer an elected official. He said the plans were stalled when the city planning staff claimed the project needed a shoreline permit because of the proximity of the lagoon. He said he successfully convinced the staff that their interpretation was in error.

In fact, Woessner has never been one to pull punches when it comes to city government, which he said has occasionally put him at odds with the city administration. During his last council meeting, he proposed disbanding the salary commission, which will soon discuss cost-of-living increases for the mayor and council even after large hikes two years ago.

In an interview, Woessner explained that while the idea of a salary commission initially seemed to be a good way to remove politics from decision making, the commission’s controversial decision to more than double the mayor’s salary made him realize that it put too much authority over legislative policy and the budget in the hands of unelected people — appointed by the mayor — who have little oversight and no greater appreciation of budget challenges.

“Sometimes the easiest route is not the best route,” he said, suggesting that the council consider the issue later this year.

During the December meeting, fellow council members, city staff and the mayor thanked Woessner for his dedication to the city and emphasized the value of his historical knowledge.

Mayor Ronnie Wright, Public Works Director Steve Schuller and Oak Harbor Police Chief Tony Slowik spoke about Woessner during a presentation, with Schuller handing him a fictitious sign for SW Jim Woessner Way. He said the staff appreciated his insights, experience as a real estate agent and as a local business owner, as well as his long history of service.

“But most importantly,” Schuller said, “we thank you for how you led, for the way you treated staff with respect, for speaking with a tone that elevated the conversation rather than question the integrity of others in the room, for showing the same courtesy and care to every community member, from the most powerful to the least in our community.”

Wright also had kind words for Woessner, saying that he learned a lot from him and will continue to do so.

“I appreciate you more than you know,” he said.

Later during council comments, his fellow council members also spoke about how they appreciated Woessner. Bryan Stucky described him as a friend and mentor.

“We’re truly losing somebody that cares, is dedicated, highly knowledgeable,” he said. “Sometimes you’re talking about stuff and I’m trying to keep up. These planning commission shoes I’m filling are going to be pretty tough to do.”

Woessner spoke briefly, which he joked was a rarity for him.

“It’s been a privilege to serve the people of Oak Harbor and give a little bit back,” he said. “You know, growing up here was a lot different place than it is now and to think that I had maybe a small part in making it just a little better.”