The Vermont Historical Society, in Barre, Vt., has posters and pamphlets from Bernie Sanders's first congressional campaign. (Jabin Botsford/The Washington Post)

A few days before Election Day in 1990, the National Rifle Association sent a letter to its 12,000 members in Vermont, with an urgent message about the race for the state’s single House seat.

Vote for the socialist, the gun rights group said. It’s important.

“Bernie Sanders is a more honorable choice for Vermont sportsmen than ­Peter Smith,” wrote Wayne LaPierre, who was — and still is — a top official at the national NRA, backing Sanders over the Republican incumbent.

That was odd. Sanders was the ex-hippie ex-mayor of Burlington, running as an independent because the Democrats weren’t far enough left. He had never even owned a gun.

But that year, he was the enemy of the NRA’s enemy.

Judy Shailor, seen July 16, 2015 in Milton, Vt., managed Peter Smith's congressional campaign in 1990. (Jabin Botsford/The Washington Post)

Smith had changed his mind about a ban on ­assault weapons. The NRA and its allies wanted him beaten. They didn’t much care who beat him.

“It is not about Peter Smith vs. Bernie Sanders,” LaPierre wrote, according to news coverage from the time. “It is about integrity in politics.”

Today, Sanders is a senator and a candidate for the Democratic presidential nomination, drawing huge crowds with his calls to break up big banks, increase taxes on the rich and make college free. The election of 1990 launched him. When Sanders won, he became the first socialist in Congress since the 1950s.

That campaign also marked the beginning of Sanders’s complicated relationship with the ­issue of gun rights — the one area where Sanders’s Democratic presidential rivals have been able to attack him from the left.

As a candidate in 1990, Sanders won over gun rights groups by promising to oppose one bill they hated — a measure that would establish a waiting period for handgun sales. In Congress, he kept that promise. The dynamic served as an early demonstration that, despite his pure-leftist persona, Sanders was at his core a pragmatic politician, calculating that he couldn’t win in rural Vermont without doing something for gun owners.

“The gun vote brought us down,” said Judy Shailor, Smith’s 1990 campaign manager. She said she had warned gun groups that, in the long run, Sanders would prove too liberal for them.

“The gun groups would say to me, ‘We are going to put him in office for one term and teach Peter Smith a lesson. Then we’re going to vote [Sanders] out,’ ” Shailor said. “I said, ‘You won’t get him out.’ . . . He’s one of the best master politicians I’ve ever come across.”

Ed Cutler, president of Gun Owners of Vermont, has mixed feelings about supporting Bernie Sanders in 1990. (Jabin Botsford/The Washington Post)

[‘Who the Hell is Bernie Sanders?’ These Southerners want everyone to know.]

Trying to break through

At the time of the 1990 election, Sanders was 49, a guy who’d had a big break and was looking for a bigger one.

He didn’t look like a politician. With his wild hair and rumpled clothes, Sanders carried himself like a man recently startled out of a nap. But he had a sharp, relentless political mind. It had taken him from a small leftist party — where the other members called him “the silver tongue” — to Burlington City Hall, where Sanders had been elected mayor by a 10-vote margin. He served four terms.

But he couldn’t take the next step. In six runs for statewide office, Sanders lost six times — including in 1988, when he lost to Smith in a close race for Vermont’s House seat.

Then, down in Washington, Smith made a disastrous, rookie mistake.

He went to a hearing. And he started to think.

The hearing was not supposed to be about guns at all. The witnesses were students who had graduated from low-performing D.C. high schools and gone on to college. Smith asked one woman what she wished she’d had more of in high school. “Courage,” the woman said. She meant courage to confront the armed bullies who taunted her on the way to school.

“It personalized something for me that had always been at arm’s length,” Smith recalled this week. “Which is that this woman lived in a culture of fear, and she faced danger and threat because of guns every day of her life.”

Just a few months before, as a candidate, Smith had promised to oppose new forms of gun control. That’s why the NRA had supported him. And the NRA support was a major reason why he had won in Vermont, where guns are associated with hunting moose and deer and not committing crimes.

But to the freshman congressman, all that didn’t seem to matter as much now.

“I’ll never forget, [the next day] brushing my teeth, looking in the mirror in my bathroom and realizing, as clear as day, I’m going to have to look at this face for the rest of my life in the mirror, and I want to be proud of the person I see,” Smith said. “I went back and looked up the gun bills.”

Smith found a bill to ban the sale of some assault weapons. He signed on as co-sponsor.

That was April 1989. Almost immediately, Smith’s office was flooded with angry cards, petitions, faxes and letters.

“I will do all I can to see that Mr Smith does not go to Washington much longer,” Pamela K. Walters of Middlesex, Vt., wrote in May, in one of the many such letters that are preserved in Smith’s papers at the University of Vermont. Someone in Smith’s House office — perhaps worn down by the vitriol and certain that the letter would never be seen again — scrawled an expletive in capital letters over Walters’s note before filing it.

Local gun groups passed out bumper stickers: “Smith and Wesson, Yes. Smith and Congress, No.” There were pictures of Smith as Pinocchio, with the caption “The Big Lie.”

“Let’s get even,” Ed Cutler, the current president of Gun Owners of Vermont, remembered thinking then.

The NRA made Smith the only incumbent that it actively opposed in 1990. The group eventually spent between $18,000 and $20,000 on advertising and direct mail in Vermont, according to an estimate from the time.

The beneficiary was Sanders, who was Smith’s main opponent in the 1990 House race. The Democrat in the race turned out to be so far left — suggesting the legalization of heroin — she made the socialist look moderate.

The unlikely alliance

The NRA-Sanders bond was an imperfect love affair.

Sanders was with the gun group on one major issue: he opposed a mandatory waiting period for handguns, saying that was best left to states. But, on assault weapons, his position was the same as the one for which Smith was getting hammered.

“It’s an issue I do not feel comfortable about,” Sanders said after one debate, according to a memoir about the race by a former aide, Steven Rosenfeld.

Sanders couldn’t very well rail against Smith for his views on assault weapons when they were the same as his own. Instead, the aide said, Sanders wanted to let others “do our dirty work for us.”

Instead of talking about guns, then, Sanders talked about honesty.

“Unlike some people, I won’t change my views on the subject,” he told one pro-gun group.

It worked.

“Bernie Sanders was upfront with us,” an NRA official wrote to one of Smith’s constituents after the race. The letter ended up in another official collection of Smith’s papers. “He was viewed as the lesser of two evils.”

As the election approached, the socialist’s good luck kept getting better.

Smith, the incumbent, invited his own party’s president, George H.W. Bush, to a breakfast fundraiser in Burlington. Then, Smith criticized the president to his face, calling for Bush to do more to tax the rich. “Like all Vermonters, Peter’s a man of independent mind,” the baffled president said when it was his turn to speak.

On Election Day, it wasn’t close. Sanders beat Smith, 56 percent to 40 percent.

Today, Sanders’s allies insist that gun control wasn’t a major reason for his victory. “A couple of percentage points, in an election that we won by 16 points,” said Jeff Weaver, Sanders’s longtime aide and his current campaign manager.

Republicans insist gun control was the most important factor in the race. “The reason Bernie Sanders got elected to Congress, beat Peter Smith, was he sided with the NRA,” said Stephan Morse, a former Republican speaker of the Vermont House and a close friend of Smith. Smith himself declined to talk about the race in an interview this week.

The correct analysis could be somewhere in between.

One poll after the election showed that about 35 percent of Sanders voters said the gun issue was a major factor in their decision.

“The NRA did not elect Bernie. But they provided much of the margin,” said Garrison Nelson, a longtime political observer at the University of Vermont.

Either way, Nelson said, the 1990 race was another step in the evolution of Sanders, who had risen from the leftist fringe by embracing allies and tactics that the fringe would not. In Burlington, he had made allies out of the police and worked out an uneasy relationship with big business. Later, in Congress, he would join the Democratic caucus, attaching himself to the party’s seniority system, after decades of railing against the Democratic Party’s politics as weak-kneed.

In the 1990 race, he made a tacit ally out of the NRA, a powerful Washington lobby that has become a chief nemesis of the left and a fierce obstacle to gun control efforts in Congress and state capitals across the country. The alliance allowed the group to bash an opponent whose positions were almost identical to Sanders’s own.

‘Bernie wants to win’

“Most socialists don’t want to win. Most socialists want to lose, because they can blame it on the system” and justify their decision to remain outside it, Nelson said. “But Bernie wants to win.”

After he was elected, Sanders stuck to the assurances he had given gun rights groups. In 1991, he voted against a measure that would have required a seven-day waiting period to buy a gun. In 1993, Sanders voted against a broader version of the bill — named for James Brady, the White House press secretary who was shot in the 1981 attempt on President Ronald Reagan’s life — that became law.

That bill set up the national background check system in place today. But Sanders objected because it also included a provision for a temporary waiting period, said Weaver, his longtime aide.

“He had been explicit with people that he would not support a federal mandatory waiting period,” Weaver said. “And he kept his word.”

Since then, Sanders has had a mixed record on guns. He supported an NRA-backed bill to shield gun manufacturers from liability lawsuits. But in 2013, in the aftermath of the massacre at Sandy Hook Elementary School in Connecticut, he backed a provision that would have tightened gun laws.

Amid his surprising rise in the presidential race, Sanders has been attacked for that record by a super PAC that backs a Democratic rival, former Maryland governor Martin O’Malley. “The NRA even paid for ads attacking a Sanders opponent?” the video ad says. “Bernie Sanders is no progressive when it comes to guns.”

[Hillary Clinton’s push on gun control marks a shift in presidential politics]

Sanders declined to comment for this article. So did LaPierre, the NRA executive who wrote the 1990 endorsement letter.

The senator has defended himself by saying that he’s uniquely qualified to lead a national dialogue on guns, since he can see the issue from both an urban and a rural perspective. And besides, he said, the NRA has given him little support.

Except once.

“In every single race that I have run, with the exception of one, the NRA and the gun lobbies and the people who are most interested in guns supported my opponent,” he told ABC’s George Stephanopoulos this year.

Among Vermont gun groups, there is some ambivalence about that long-ago election.

“In some ways, I’m happy that it happened. And in some ways I seriously regret it,” said Cutler, of the Gun Owners of Vermont. “I’m happy I did it, because it sent a message around the state that the gun vote really does count around here.”

But now, Cutler said, when he calls Sanders’s office to ask for a meeting, he never gets one. “I regret that it happened,” he said, “because, realistically, we have no input with him.”