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BURLINGTON, Vt. — Bernie Sanders says that if he is elected president, he will convince skeptics to support his agenda by building a movement so powerful that they will have no choice but to join him.

It is the same thing he says happened when he was mayor here in the 1980s, his only experience as a chief executive to date. “Democrats, Republicans were not stupid,” Mr. Sanders said in an interview in his campaign office. “And they looked around and they said, ‘Oh my God, we thought this guy was a fluke, he’d come and he’d go, [instead he] is further transforming politics in this city’…. So they started working with us in a much more constructive way.”

Mr. Sanders says his opponents came to their senses and joined him. But a close examination of the Vermont lawmaker’s record as mayor shows that at times he also went to them, working with Republicans, police and business on key issues facing the community—sometimes to the frustration of his liberal allies.

“The city was run in the 1980s as a coalition between what you would now call the progressives and the Republicans,” said John Franco, assistant city attorney in the Sanders administration. “Bernie is a fiscal conservative. The saying in Vermont is he’s tighter than the bark on a tree.”

The Wall Street Journal interviewed more than a dozen people who lived and worked in Burlington from 1981 to 1989, including Mr. Sanders and his wife, Jane, at the time the director of the Youth Office. What emerges is a picture of an executive who had the same goals for governance as he does today, but won favor with Republicans when his administration audited the city’s finances, joined with the business community on a controversial development project and once sided with the police and factory workers over protesters.

“He’ll listen to the points of the other person. And as long as the goal is not just to, you know, feather the nests of the wealthy,” he will work with people, Mrs. Sanders said.

It is a period that the senator doesn’t often discuss on the campaign trail. His deal-making past could help him reach out to centrist voters but could also alienate supporters who are looking for an uncompromising candidate to upend the system. (On a recent episode of “The View,” Mr. Sanders struggled to name a Republican he worked with who wasn’t dead or retiring.)

Louie Manno, a radio host here in the 1980s, said Mr. Sanders did a “pretty good job” as mayor because his governing was less radical than his campaigns.

Mr. Manno is a supporter of President Trump, but he said he isn’t worried about a Sanders presidency upending the country: “If he became the president of the United States, we’d still be a free-market economy, we would still have an army, we’d still have a Second Amendment.”

Shortly after Mr. Sanders, an independent who identified as a Democratic socialist, was first elected mayor, by just 10 votes, Mr. Franco and Sandy Baird, a progressive activist and lawyer who later became a state representative, were standing in the city’s courthouse. Ms. Baird remembers Mr. Franco turning to her and proclaiming: “Welcome to the revolution.”

But in his first term in office, one key initiative of Mr. Sanders’s administration was more quotidian: Cleaning up the city’s finances, a move that earned trust from some Republicans. Mr. Franco said they wanted to prove to skeptics they knew how to govern.

The Sanders administration audited the city’s finances and found a surplus of nearly $2 million, which it invested into capital improvements.

Mr. Sanders also formed some alliances with the business community over the Burlington waterfront, which local developers wanted to revamp. Mr. Sanders said during his campaign that the city wasn’t for sale. But once in office, he decided to back a commercial development plan.

After that idea fell apart amid progressive resistance, the Sanders administration pivoted to a development vision focused on public access, the basis for the current waterfront, which includes a bike path and dog park.

Mr. Sanders considers the waterfront a significant piece of his legacy and held his 2016 presidential kickoff rally in a spot framed by Lake Champlain and the mountains.

Peter Clavelle, who succeeded Mr. Sanders as mayor and oversaw the final stages of waterfront development, said Mr. Sanders’s involvement with the business community helped make it happen.

“Bernie was not just the rabble rouser,” said Mr. Clavelle, who was the first director of the Community and Economic Development Office under Mr. Sanders.

David Thelander, a GOP-aligned independent on Burlington’s Board of Aldermen at the time, said he found Mr. Sanders receptive to economic development proposals.

But some progressives never got over Mr. Sanders’s support for a more commercial waterfront.

“One of the things that really bugs me about him is that he always claims he never changes his position, that he is consistent in everything that he does. This is one of the really big inconsistencies about Bernie,” said Rick Sharp, who runs Burlington Segway tours and opposed commercial development of the waterfront.

Mr. Sanders again found himself on opposite sides of progressive activists in June 1983, when hundreds of antiwar activists protested General Electric Co. for making military weapons at a plant here. Greg Guma, a progressive journalist who was involved in the antiwar movement, remembers telling Mr. Sanders of the plans to protest.

“He was very upset with us,” said Mr. Guma, who wrote a book about Mr. Sanders’s tenure as mayor. Mr. Sanders told the group to demonstrate at congressional offices instead, Mr. Guma said.

Mr. Sanders followed up with a call to tell Mr. Guma that if he protested at the plant, he would be arrested. Mr. Guma went anyway. Eighty-eight people were arrested, including Mr. Guma, who went back to the protest after getting out of jail and was arrested again. Mr. Sanders observed the arrests and didn’t intervene, Mr. Guma said.

“My view was you had hundreds and hundreds of jobs that were decent-paying union jobs. You shut them down here, they’re just going to move someplace else,” Mr. Sanders told The Wall Street Journal.

Some of those same protesters who stood outside the General Electric plant more than three decades ago now stand outside Mr. Sanders’s Senate office on Church Street to protest his support for basing F-35 fighter jets at the Burlington Airport. As with GE, Mr. Sanders says he supports the F-35 program because of the local jobs involved.

While Mr. Sanders did occasionally make surprising alliances, he still had plenty of critics—especially establishment Democrats. Mr. Sanders beat an incumbent Democrat for the post and that first year the Board of Aldermen attempted to block his every move and his cabinet. Despite working with Republicans on occasion, he had a GOP opponent every election cycle.

Ernie Pomerleau, a Republican developer, said he worked with the Sanders administration at times. But he always tried to sink Mr. Sanders when election time came around. Mr. Pomerleau said that one campaign cycle, he informed Mr. Sanders that his friends had been encouraging him to be Mr. Sanders’s campaign manager.

“Why?” asked Mr. Sanders.

“Everybody I have supported has lost,” Mr. Pomerleau replied.

Mr. Sanders laughed.