Michael Kruse is a senior staff writer for Politico.

The night of April 19, 1988, in the tense, people-packed auditorium at Burlington High School in Burlington, Vermont, Bernie Sanders strode stern-faced into enemy territory.

The city’s crotchety, socialist, obstinately independent mayor planted himself at the center of the stage at the Democratic Party’s caucus, an event he had never once participated in, stood behind the lectern and drilled into the audience a five-minute speech in which he backed the Rev. Jesse Jackson. He praised the Baptist minister and civil rights activist as “a candidate for president who has done more than any other candidate in living memory to bring together the disenfranchised,” “a candidate who is creating a historic coalition, of working people, of poor people, of women, of minorities, of students, of farmers, of peace advocates, of environmentalists” and “a man who has waged the most courageous and exciting political campaign in the modern history of our nation.”


The crowd kept calm as Gov. Madeleine Kunin spoke in support of Michael Dukakis, the governor of neighboring Massachusetts and the clear establishment favorite. But then someone else, backing Tennessee Sen. Al Gore, took the opportunity to censure Sanders as an “intruder” who wanted to “undermine and destroy the Democratic Party.” And this sparked the already primed crowd, which exploded with a mixture of boos and cheers. A local Democratic leader rushed to the microphone and pleaded for unity, civility and calm.

It didn’t quite work.

A little old lady in the rear of the room yelled that she wanted “unity among ourselves,” not with “outsiders,” and minutes later buttonholed Sanders in the post-vote scrum and slapped him on the cheek. The woman told a reporter she had slipped and “accidentally hit him.” Sanders didn’t believe it, but no charges were filed. He knew he was the one who had landed the far more substantial blow by endorsing an insurgent African-American candidate who made the Democratic Party deeply uncomfortable. “By the way,” Sanders would say, in a coy boast tucked into his midcareer memoir, “Jackson won the Burlington caucus overwhelmingly. He also carried the state.”

Over the years, this volatile evening has receded into the past as Jackson and Sanders went their largely separate ways—Jackson becoming an ally and adviser to Bill and Hillary Clinton while continuing his advocacy for peace, civil rights and economic justice, Sanders taking his own unlikely path from small-city executive to two-time presidential aspirant himself. But many supporters and advisers at the outset of Sanders’ second run for the White House want him to talk about it more, to feature it as part of his unusual and historic political biography. Nodding to the importance of humanizing a candidate whose rigid focus on policy often has obscured his personal story, they see his endorsement of the first African-American presidential candidate who had any chance at all as a courageous and telling part of his tale that also could serve as a useful tool to boost his largely lagging support from black and brown voters. Nina Turner, a campaign co-chair, earlier this month called Sanders “a visionary” in this respect. She wishes he would claim that mantle as part of this increased effort to connect his life experience as a young civil rights activist and a son of immigrants to his well-honed message of economic inequality. “He has to,” Turner told me. “He has to go deeper this time around.”

Civil rights activist and Baptist preacher Jesse Jackson stands in the center of fellow presidential primary candidates, from left, Sen. Paul Simon (Ill.), Gov. Michael Dukakis (Mass.), Rep. Richard Gephardt (Mo.) and Sen. Albert Gore (Tenn.), who look on as former Sen. Gary Hart (Colo.), not shown, answers a question following their debate. | AP Photo/Jim Gerberich

Sanders’ endorsement of Jackson is of a piece with his civil rights work of the early 1960s; in ’88, after all, he “stepped across the color line,” as Jackson has put it, doing something very few other white elected officials did that year. But Sanders has mentioned his Jackson endorsement only sporadically and selectively over the years. That’s partly a reflection of the reality that what drove Sanders’ decision was not really the color of Jackson’s skin—it was their mutual belief that corporate and political power brokers had rigged the system against the poor and working class. “Our kinship was on a shared vision of the country, a shared vision of the issues,” Jackson told me. “We was talkin’ the same talk.”

What happened that night in Burlington was as much about the emergence of Sanders’ nascent national ambition, too, as it was about his support for Jackson. The endorsement was revealing because it captured Sanders at a pivotal moment in his political evolution—spotlighting him not only as a trailblazer but also as ambitious and newly adaptable, not just blunt but shrewd, a realist as much as an idealist. He was 46. He was in his fourth and final two-year term as mayor. He already had garnered some renown, the “red mayor in the Green Mountains,” in the words of Rolling Stone, but he wanted more. He had run for governor two years before, unsuccessfully, and he had just announced a run for Congress, both bids made pointedly and stubbornly as an independent. To get where he wanted to go, though, he was going to have to beat candidates who were Democrats in a statewide race. And to do that he was going to need to earn Democratic votes. His endorsement of Jackson—a charismatic populist, an outsider, but an outsider who was gunning for the Democratic nomination—would help him do that. Sanders’ fractious appearance at the Vermont caucus marked the first time—the only time, in fact, until he started running for president in 2015—that he opted to operate within the electoral process of the party he so frequently had scorned as almost indistinguishable from Republicans on matters of economic fairness.

After multiple failed runs in statewide elections, Bernie Sanders runs for and is elected mayor of Burlington, Vt. in 1980, as a self-described socialist. Sanders, seeing (clockwise) outside a polling place in 1983, picking up litter at a local park in 1981, and singing in a local recording studio in 1987, would serve for eight years before moving on to higher office. | AP Photo/Donna Light, Rob Swanson, AP Photo/Toby Talbot

“His endorsing Jackson,” Karen Glitman, a leader in Jackson’s previous ‘84 campaign in Vermont, told me, “was sort of a nod to the Democratic Party.”

Some Sanders allies and confidants downplay the notion of any calculation of this kind. “He didn’t think like that,” Terry Bouricius, a progressive former member of the City Council in Burlington, told me. “No, no, no,” said longtime Sanders staffer Phil Fiermonte. But even they grant that Sanders had his eye on what was to come. “Everybody knew,” Bouricius said, “that Bernie was going to run for higher office.”

“He’s a very, very smart politician, with a lot of acumen,” Maurice Mahoney, a onetime head of the Democratic Party in Burlington who often butted heads with Sanders when he was on the City Council, told me, “and he knows how to sort of lay the groundwork for his future.”

“He’s a realist,” Liz Blum, who ran Jackson’s ’88 campaign in Vermont, said of Sanders.

1984

“Tonight, we come together ...

inheriting the legacy of a great party, the Democratic Party, which is the best hope for redirecting our nation on a more humane, just and peaceful course. This is not a perfect party. We are not a perfect people. Yet, we are called to a perfect mission.” Jesse Jackson, DNC Address 1988

“I always have a little bit of a problem because I’m not a Democrat and I’m not a Republican. … My dream would be that we would have a strong third-party movement in the United States composed of working people and minorities ... but that doesn’t exist right now, so my options are somewhat limited.” Bernie Sanders on C-SPAN as Mayor of Burlington, Vt.



So he went to the caucus. “It’s his way of forming a partnership,” Jean O’Sullivan, the city’s top Democrat at the time and the woman who had to scamper onto the stage and beg for serenity, told me. “It was pragmatic—but it was brash.”

Which was one reason a woman slapped him in the face. Sanders, according to local news reports, seemed momentarily stunned. “I don’t think that was very nice,” he managed to stammer. “It was,” Sanders would deadpan in the memoir, “an exciting evening.”

But it was more than that. It was the evening the Bernie Sanders of Burlington shifted most markedly and publicly toward becoming the Bernie Sanders with coast-to-coast clout of today—the willful, indefatigable septuagenarian, who recently registered to run for president as a Democrat and signed a “loyalty pledge” but also filed for reelection to the United States Senate as an independent, armed with at least the begrudging respect of a party establishment he continues to poke, and secure in his stature as the longest-serving independent in the annals of Congress. For some, that spring night 31 years ago in Vermont is a defense against a perceived vulnerability of Sanders, that he is not sufficiently attuned to the currents of identity politics. But for many who have tracked Sanders’ career from the start, this moment is an origin story in which Jackson’s run helped shape Sanders’ stature as one of the front-runners to become the Democrats’ 2020 nominee.



***

It took years, and more than a little persuading, to get Sanders to support Jackson—in many ways an irritant to the establishment, whose ultraliberal platform mobilized and prioritized minorities, farmers, gay people, poor people, the have-nots and the left-outs.

In 1984, contrary to a variety of previous reporting and even some stray suggestions from Jackson, Sanders did not endorse him during his first presidential campaign. When Jackson stopped in Vermont that year, he and Sanders met in the mayor’s office in “a closed-doors meeting,” according to UPI. They agreed, Sanders told the Burlington Free Press, that “there’s a lot better uses for people’s tax dollars than supporting military dictatorships.” Jackson, Sanders said, was “an interesting, dynamic man.”

But Sanders mostly gave him “the cold shoulder,” Ellen David Friedman, a key progressive organizer in the state who was a close Sanders associate as well as a vigorous advocate of Jackson and his Rainbow Coalition, would recall. Asked whether he would endorse Jackson, Sanders responded by telling the reporter from the Free Press he wasn’t a Democrat, and so he would not “involve himself in Democratic politics,” as the paper put it. (Jackson that year got 8 percent of the vote in the Vermont primary but won five primaries and caucuses mainly in the South before finishing third overall behind Walter Mondale, whom Sanders reluctantly backed in the general election, and Gary Hart.) This stiff-arm was a surprise to nobody who had been paying attention to Sanders’ career to that point.

Rev. Jesse Jackson, top left, first ran for president in 1984, mobilizing a diverse base of supporters he would dub the “Rainbow Coalition.” | AP Photo/Al Stephenson, Jacques M. Chenet/CORBIS/Corbis via Getty Images, Barbara Alper/Getty Images

By 1986, however, the Rainbow Coalition that Jackson’s ’84 campaign had spawned had grown in power in Vermont. Sanders, who was running for governor, couldn’t ignore it. Nor, however, could the state’s energetic contingent of Jackson devotees avoid Sanders, considering the sway he had over progressives in Burlington and beyond. A symbiosis between the two outsiders started to materialize. Sanders didn’t join the Rainbow; he wasn’t much of a joiner, period. But he “realized the necessity of participating in broader coalitions if he was ever to take his vision beyond the city limits,” progressive organizer and journalist Greg Guma of Burlington wrote in his 1989 book, The People’s Republic: Vermont and the Sanders Revolution. “He was looking to hold onto that base of support so he could challenge from the outside,” Guma told me.

And at the heart of this messy, contentious, sometimes controversial connection was Friedman. She was a founding member of the Rainbow Coalition of Vermont. She was also, though, the national committeewoman for the Vermont Democratic Party. And she was helping to manage Sanders’ gubernatorial campaign—challenging Kunin, Vermont’s first (and still only) female governor, and a Democrat, who generally considered Sanders a vitriolic troublemaker. Friedman worked for Sanders for the same reason she worked for Jackson: “He’s somebody who is able to energize and empower regular people who are not normally politically active—poor people, working-class people.” Friedman would write, “Sanders is a complicated player in a complicated game, yet his favorite summary for any political conundrum is, ‘Look, it’s really not all that complicated,’ meaning, almost invariably, ‘We are acting out the class struggle, and any situation can be analyzed in that light.’”

As Jackson geared up for a second presidential candidacy that felt like a more organized, more robust extension of the first, the two aligned. Jackson endorsed Sanders’ gubernatorial bid. “In my judgment,” Jackson said at the Rainbow Coalition’s national conference that spring, “supporting Bernie represents a step toward sane and sensitive public leaders.”

After a failed longshot bid for governor as an independent in 1986, Sanders, left, would go on to endorse Jackson’s second outsider campaign for the Democratic nomination for president in 1988. Jackson, right, would also be unsuccessful, but the experience for both men may have set the stage for Sanders’ current attempt at the party’s presidential nomination. | AP Photo/Toby Talbot, Darlene Hammond/Hulton Archive/Getty Images

Sanders welcomed the backing and returned the compliment.

“The Rainbow Coalition is moving very rapidly and very aggressively, all over the state of Vermont,” Sanders said at the conference. “And I think the goal is that if we all stand together,” he added, “white and black and Hispanic and Asian, American Indian … I think the opportunity is there. Let’s get together, and let’s take back this country.”

“By him moving under that umbrella, he wasn’t going to lose anything,” said Tom Smith, a progressive in Vermont at the time and a former Burlington city councilor. “He was going to help Jesse; he was going to help himself.”

In helping himself, Sanders played, too, into some of the other main critiques that would dog him in 2016 and still do now—that he was blind to how African-Americans saw race, not class, as the main obstacle in their way, and that he was undermining the Democratic Party by holding himself apart from it while at once using it to his benefit.

His emerging pragmatism had its limits. In the wake of getting just 15 percent of the vote in his gubernatorial bid, Sanders in late 1987 applauded Jackson but copped to ongoing ambivalence about party politics. “I think you would have to be crazy not to understand that Jackson has had an important impact on the American political scene,” he said in an interview with a student publication at the University of Vermont. There was a but, though: “I disagree with working within the Democratic Party, OK?”

1988

“Common good is finding commitment to new priorities to expansion and inclusion, a commitment to expanded participation in the Democratic Party at every level, a commitment to a shared national campaign strategy and involvement at every level.” Jesse Jackson, DNC Address 1990

“I don’t have a party hierarchy on top of me and it gives me a little bit more freedom to speak out on all of the issues. I think that by and large in this country today there is a growing anger and frustration not only at Congress ... but at the two-party system.” Bernie Sanders to C-SPAN as a new Congressman-elect



And he showed a tendency to dismiss the racial anxieties of African-Americans, who were still nursing the wounds of decades of legalized discrimination. “What Jackson has going against him, in my view, is not primarily that he’s black,” Sanders told a C-SPAN caller in January 1988. “I mean, there are some people who won’t vote for somebody who’s black, and that’s that. That’s a minority. … Let me say that one of the nice changes that has taken place in the last 20 or 30 years is that in fact a person like Jesse Jackson can run for president of the United States and be taken seriously. … I think the issue is not a racial issue. I think it’s a class issue. OK? … The real issue is whose side are you on? Are you on the side of workers and poor people, or are you on the side of big money and the corporations? Jackson is on the side of poor people and working people.”

Despite this ideological overlap, heading into the thick of the primaries in the early months of the ’88 campaign, Sanders still wasn’t ready to endorse Jackson.

“His issue was how far would he go in getting involved in the Democratic primary process and the Democratic Caucus process,” Terje Anderson, the current chair of the state Democratic Party and a retired AIDS activist who knew Sanders at the time, told me. “That was the barrier for him.”

It was Friedman who finally persuaded him to abandon his dogmatic opposition. “I was persistent,” she told me.

The choice in some sense, too, was made easier by the relative success of the Jackson campaign. The ’84 race, said Richard Hatcher, Jackson’s campaign chairman that year, “was basically a symbolic campaign.” But by 1988, adviser Ann Lewis said, it was “a real campaign.” Jackson remained a long shot—but no longer was he a no-shot. On February 8, Jackson finished fourth of five in the Iowa caucuses, behind Dick Gephardt, Paul Simon and Dukakis—but still got 8.8 percent of the vote. Sanders endorsed him the next day. Jackson’s ideas, Sanders said at the time, were of “far greater significance than anyone else.” He was the only candidate “who has built a coalition of those who are not being treated fairly by society,” Sanders continued, calling that “a very exciting development.”

Sanders hosted Jackson that week in Burlington. Sanders called the visit “a great pleasure.” Jackson said he was “delighted” by the endorsement. Sanders touted Jackson in a rousing introduction in a local landmark chapel. “The state of Vermont happens to be the whitest state in the United States of America,” Sanders said. “ … The great political geniuses and the political scientists and the media, they have decided that our candidate can’t become the president of the United States because they believe that white people are not going to support him. … The fact of the matter is that if Jesse Jackson can carry Vermont on March 1 … the message will go out all over the United States that this man is going to become the next president of the United States.”

Breaking his abstention from getting involved in party politics, Sanders announces his support for Jackson in late 1987 and would go on to endorse the Democrat and caucus for him in 1988. | AP Photo/Toby Talbot; Silver Special Collections, University of Vermont

“Compared with his hands-off approach to Jackson in 1984,” Friedman would write, “this time around Sanders was a visible and enthusiastic supporter.”

“Once he was on board, he was, you know, fully on board,” said longtime staffer Fiermonte.

On March 1, in the primary in Vermont, which was nonbinding—the caucuses were what counted—Dukakis won with 57 percent, but Jackson placed second with 26 percent. Sanders called the showing “extraordinary” and “fantastic.” And after Jackson won five primary states on March 8 on Super Tuesday in the South and then won the Michigan primary on March 26 with an eye-opening 47 percent of the vote, Sanders kicked up his commitment: On March 30, he said at a press conference that he would do something he had never done in his nearly two decades as a politician.

2016

“There’s a tug of war going on for the soul of America. We have a clear choice. We must tear down walls of separation, and build bridges of hope and unity.” Jesse Jackson, DNC address

2016

“The Democratic Party needs leadership which is prepared to open its doors and welcome into its ranks working people and young people. That is the energy that we need to transform the Democratic Party.” Bernie Sanders, presidential campaign speech

“As someone who is not a Democrat, or a Republican, I personally have never attended a caucus of either major political party,” he said, speaking on behalf of progressives around the state. He said the Jackson candidacy would be remembered as “the most significant presidential campaign in at least 50 years.” He said it would be “irresponsible” not to go, though he acknowledged it would be “awkward” given the years of antagonism between him and the local Democrats.

A reporter asked Sanders if this represented a “milestone” in his political career. Sanders said no. But his answer suggested the opposite. “When you’re dealing with life-and-death issues of what’s going to happen to this state and to this nation, you’ve got to be fluid,” he said. “You’ve got to be flexible.”

Many Sanders-led progressives bought the argument. “Bernie prevailed,” Bouricius told me. “Bernie convinced me it was an experiment worth trying.”

The buildup to the evening of the caucus was full of saber-rattling and temperature-taking. Craig Fuller, the executive director of the state party, contacted Jackson’s national campaign headquarters to complain. “I would prefer to have a Democrat nominate a Democrat at a Democratic caucus,” he said. Blum, the Vermont leader of the Jackson campaign, dismissed the request as “absolutely ridiculous.” Sanders, for his part, seemed to enjoy the hubbub. “I find it a bit amusing,” he said. “I have no apologies to make to anybody,” he added. He arrived with leaflets listing reasons he was supporting Jackson—and also asked people to contribute to his own “historic” campaign for Congress.

O’Sullivan did her best, she recalled, to make the affair less fraught. She opened the evening, she told me, by referencing the Port Huron Statement of the Students for a Democratic Society, citing the manifesto’s principles of a participatory democracy. O’Sullivan’s point: “We’re all in this together, folks.”

Sanders strode to the stage holding the notes for his speech and leaned into the microphone.



***

What Sanders did and said that night mattered.

Jackson, a month and a half after he lost to Dukakis in the nonbinding primary by 31 points, won the Vermont caucuses—edging Dukakis 46 to 45 percent. The outsider had bested the party establishment guy, and in his backyard no less. It presaged, in some ways, Sanders’ own upsets against Clinton in 2016 when he trounced her in New Hampshire on the way to winning 23 primaries, stretching the contest into late spring.

It’s impossible to quantify the precise effect Sanders’ support might have had. Jackson campaign staffers say their furious organizing efforts closed the gap. But after that? “I think Bernie might’ve made the difference between winning and losing,” Steve Cobble, the campaign’s national delegate coordinator, told me. “He was, without question, the leader of progressives in Vermont,” Glitman said. “If Bernie had not really convinced a bunch of us to go to the Democratic caucus to support Jackson, I don’t think Jackson would have won the Burlington caucus—there were a lot of progressives there,” Bouricius added. “It was,” Jackson told me, “very valuable.”

Taking a page from fellow outsider Jesse Jackson’s 80s playbook, independent Sanders, top, announces his candidacy for the Democratic Party’s presidential nomination in May 2015. Below, Sanders speaks alongside Jackson, who, having close ties with the Vermont senator as well as Hillary Clinton, refrained from endorsing anyone in the 2016 primary. | Rick Friedman/Corbis via Getty Images, AP Photo/Nam Y. Huh

As impressive as it was, though, the showing in Vermont led to only so much additional propulsion for Jackson’s campaign—he lost the more important New York primary the same day—and Dukakis, of course, ended up as the nominee. Jackson’s ’88 president campaign was his last, and the Rainbow Coalition gradually lost influence.

It’s was Sanders who ultimately got more out of the association. That year, he didn’t win his race for Congress, but he lost by only 3.7 percentage points—siphoning votes from the Democrat, whom he beat handily. Two years later, he ran for the seat again, and won—and he hasn’t lost an election in Vermont since. He jumped from the House to the Senate in 2006. And to Garrison Nelson, a political science professor at the University of Vermont, it all started in 1988. “It’s a real breakthrough for him,” he told me. “That was really a wake-up call that Bernie could deal with the Democratic Party … and had some power to influence voters, and influence voters within the Democratic Party, as opposed to his general stance of blatant opposition to the Democratic Party.”

Sanders also drew from his involvement with Jackson’s presidential push a model for his own.

In May 2015, when Sanders met with the editorial board of the Quad City-Times based in Davenport, Iowa, he was asked which presidential campaigns from the past might inform his. He cited Franklin Delano Roosevelt’s campaign of 1936—and the ’88 Jackson campaign. “People forget about this,” Sanders said, “but Barack Obama would not be president today if Jesse Jackson didn’t come to Iowa. That was a guerrilla-type campaign that clearly didn’t have resources but had incredible energy.”

“He took from what Jackson did in ’87 and ’88,” Cobble said, “that you could put issues that had been ignored directly into the center of the public process by running for president and stating your message correctly. And if you did it well, you would find surprising support for it that not very many people recognized was there before you ran.”

“It really is the same template,” said Turner, the Sanders co-chair.

Echoes from Jackson’s campaigns in Sanders’?

“Loud and clear,” Jim Hightower, one of only a select few other white elected officials who endorsed Jackson in ’88, told me. “You’ve got a clear sense of who you’re trying to help, and a clear sense of who you’re willing to piss off.”

Supporters, surrogates and staff of Sanders’ now-second bid for the Democratic nomination have invoked on the campaign trail his past endorsement of Jackson—as one of the only white politicians at the time to do so—in efforts to bolster his credibility on racial issues. | Scott Eisen/Getty Images

During his 2016 campaign, Sanders met with Jackson in the wake of his difficulties with Black Lives Matter protesters, who heckled him at multiple appearances, challenging him to address their concerns about police killings of black men.

“Longtime friends,” a Sanders spokesman said of Sanders and Jackson. “Bernie endorsed me in ’88, and I won Vermont, at a time that it wasn’t a popular thing to do,” Jackson said heading into the Iowa caucuses. Jackson, however, did not endorse Sanders in 2016. Sanders, however, mentioned his endorsement of Jackson two weeks before the South Carolina primary, where African-American voters make up 28 percent of the population and 55 percent of the Democratic electorate. “I thought what he was saying made sense,” he said. “I had the courage to do that.” And he mentioned it later in the spring at a gathering of the Rev. Al Sharpton’s National Action Network. “I had to take on the whole Democratic establishment in the state of Vermont,” he said.

So far in his 2020 campaign, in stops in Brooklyn, Chicago, Iowa and New Hampshire, some supporters, staffers and surrogates have invoked the ’88 Jackson endorsement. Sanders has not. It hasn’t been a part of his stump speech, which is a version of what essentially always has been his stump speech, a finger-jabbing, stats-laced broadside about “the billionaire class” and this country’s long-running and worsening systemic economic inequities.

He did mention it in a recent interview on the syndicated radio show called The Breakfast Club. “In 1988,” he told co-host Charlamagne tha God, “I was one of the few white public officials who supported Jesse Jackson for president of the United States …” But Sanders also was still … Bernie Sanders, the candidate for whom class has always trumped race. “We’re going to pay attention,” he said, “to the needs of working families and low-income families in this country in a way you’ve never seen.”