On a crisp Monday night earlier this month, Amtrak police at New York’s Penn Station escorted Bernie Sanders off the train from Washington and into ClubAcela. The just-declared presidential candidate, spotting a phalanx of body guards, asked his escort what VIP was in their midst.

“You could have the primary debate right now,” came the response. It was Hillary Clinton.


Sanders passed along a note asking if he could come say hello, she said yes, and the two passed 10 cordial minutes.

“She genuinely seemed happy to see him,” said Richard Sugarman, Sanders’ close friend and former roommate, to whom he relayed the story of their chance encounter. “He said it was almost impossible not to feel for her — how isolated she was, and how insulated she was. And he came away from that saying, ‘What can I tell you. It’s not easy being her.’ ”

This wasn’t the first time Sanders has reached out to Clinton. He’s been doing that for more than 20 years. As one of Congress’s most liberal members in the 1990s, Sanders went back and forth between clashing with Bill Clinton and warily embracing the leader of the centrist New Democrats. But even before the Clintons were in the White House, Bernie was playing the role of pragmatic progressive, making overtures directly to Hillary and working to pull her to the left.

In 1992, the lone socialist in Congress, Rep. Bernard Sanders, as he was then known, wasn’t wild about the centrist Arkansas Governor running for president, and he let it be known publicly. “Bernie was the founder of the progressive caucus. Clinton was the founder of the [Democratic Leadership Council], the whole point of which was to exterminate the progressives,” said Bill Curry, who served as counselor to the president during Clinton’s first term. “They weren’t even two ships passing in the night. They were two ships sailing in the opposite direction.”

But in May of 1992, Sanders wrote to the First Lady of Arkansas at her Little Rock law firm to tout a bill he had written to provide federal funding for state cancer registries, attaching his testimony on the bill’s behalf and a Reader’s Digest article calling registries “THE CANCER WEAPON AMERICA NEEDS MOST.” Though there’s no record of a response from Little Rock, Sanders would grab the Clintons’ attention soon enough.

The next month, as the newspapers gamed out the three-way race between Bill Clinton, the incumbent President George H.W. Bush, and independent Ross Perot, they speculated that the first-term congressman from Vermont could become an unlikely kingmaker if the election got thrown to the House, where, as the lone representative from Vermont and an independent, his swing vote would control his state’s delegation. The Washington Post suggested that, in such a scenario, Bush might promise to make Sanders secretary of health and human services in return for his vote. The presidential campaigns were reportedly reaching out, just in case.

That summer, Sanders issued what the Vermont newspapers described as a “reluctant” and “half-hearted” endorsement of Clinton, saying that a second Bush term would be disastrous. In September, Clinton traveled to Vermont for a campaign rally in Burlington at Perkins Piers on Lake Champlain. Sanders was in attendance, and Clinton made sure to point out just how vast the gap was between Sanders and the Republican nominee on Sanders’ pet issue: health care.

“Now folks, there’s a lot of other things I want to say. But every time I say that old George Bush says, ‘Bill Clinton is going to give you a health care system with the compassion of the KGB and the competence of the House Post Office,’ I would remind you — maybe Bernie Sanders ought to be reminding you — I’ll remind you — George Bush has had the benefit of socialized medicine for the last 12 years,” said Clinton. “Maybe we ought to send him home and put him in like the rest of us in the system we’ve got and he can figure out whether he likes it or not.”

Clinton’s election in November marked the ascendance of the New Democrats and the ideological exile of progressives. But Sanders apparently concluded he could still curry influence with one key member of the Clinton team: the first lady.

One of Bill Clinton’s first acts in office in January of 1993 was to appoint his wife to chair the administration’s Task Force on National Health Care Reform. Sanders had convened his own, much-smaller task force pushing single-payer health care for Vermont, and he began trying to pull Hillary Clinton in that direction.

In February, Sanders requested a meeting with Hillary, “to bring in two Harvard Medical School physicians who have written on the Canadian system,” according to the records of the administration’s task force. Those physicians were Stephanie Woolhandler and David Himmelstein, leading advocates for single-payer health care.

They got their meeting at the White House that month, and the two doctors laid out the case for single-payer to the first lady. “She said, ‘You make a convincing case, but is there any force on the face of the earth that could counter the hundreds of millions of the dollars the insurance industry would spend fighting that?’” recalled Himmelstein. “And I said, “How about the president of the United States actually leading the American people?’ and she said, ‘Tell me something real.’ ”

Sanders was undeterred by this dismissal of single-payer’s political viability. In March, he was at it again, inviting the first lady up to Vermont as the state considered overhauling its own health care policies. In June, Clinton did go up to Vermont – to address a Democratic Governors Association meeting hosted by the state’s then-Gov. Howard Dean in the quaint village of Woodstock – and she brought Sanders and Sen. Pat Leahy with her.

The administration’s background briefing on Sanders, tucked in with its plans for the trip, notes, “As a relatively junior member without the support of major party backing, Sanders is not much of a factor legislatively. He is a cosponsor of Congressman McDermott’s single-payer bill and given his reputation for independence and his somewhat combative style may be one of the more difficult Members to get on board the Administration’s proposal.”

On the eve of the trip, Sanders scored a meeting with the president in Washington. The task force’s record of the meeting speaks to the complexity of his relationship to the Clintons. “Accounts were that it was cordial, focusing more on process than substance. He urged the President to get out into the country more to sell his plan himself rather than letting the press define it. Given the sensitivities within the delegation, the Senators may be somewhat jealous of this meeting. In addition, there have been reports that the Congressman will be participating in an event on Saturday critical of both the welfare and health care reform efforts of the Administration.”

During her trip to Woodstock for the DGA meeting, Hillary Clinton’s remarks touted a grant secured with Sanders’ help from the Department of Labor for 800 “dislocated” Vermont workers. It presaged a looming conflict between Sanders and the Clintons on globalization that continues to today and the fight over the Trans-Pacific Partnership.

After lunch, Sanders, Leahy and Dean accompanied the first lady for a stroll down the town’s main drag with photographers and cameramen trailing them in a horse-drawn wagon from Billings Farm and Museum.

The DGA meeting and Clinton’s visit live on in local memory, though Sanders’ participation has mostly faded (then-Clinton adviser Paul Begala’s only memory of the trip is a stop for ice cream on the stroll).

“There was so much attention on her that even Leahy – everything was in the background to her. And she had a beautiful red outfit on, so she really stood out,” said Jireh Billings, owner of a general store where Clinton stopped to purchase maple syrup. In the souvenir photo Billings keeps of the encounter, the top of Sanders head is just visible directly behind Clinton, who stands in the middle in brilliant red. Any semblance of influence over the Clintons’ health care plans soon faded as well.

In July, Sanders again wrote to the task force about a single-payer system, his letter cataloged in a White House mail log among thousands of others from the hoi polloi. He was back on the outside, lobbying the administration on CNN rather than in person.

“I think Mr. Clinton should start talking about class issues — which he did somewhat in the campaign, I think successfully — and talk about the gap between the rich and the poor; the fact that the richest 1 percent now owns more wealth than the bottom 90 percent,” said Sanders that month on Larry King Live.

In September, Bill Clinton announced a plan that relied heavily on an employer mandate to provide insurance for workers. John Franco, a Burlington lawyer and member of the single-payer task force, said the first lady’s staff did ultimately assure Sanders’ crew that the administration’s plan wouldn’t preclude Vermont from pursuing single-payer at the state level. (But Dean, a physician, opposed single-payer and Vermont’s health care reform push would eventually fizzle amid discord. The state’s renewed efforts to implement a single-payer system collapsed late last year, taking the political prospects of current Gov. Peter Shumlin down with them).

By October, Sanders’ next invitation for the Clintons to come to Vermont was not in a note to the White House, but in a hostile letter to the editor in The New York Times. “You report Oct. 25 that President Clinton believes the economy has turned the corner, on the path of a steady recovery. To get a better perspective on this view I urge the President to visit Vermont, where in the last year a Digital plant has closed, St. Johnsbury Trucking has closed, Johnson Controls is planning a shutdown, I.B.M. and G.E. have slashed hundreds of well-paying jobs, and workers from several companies are negotiating give-back contracts,” wrote Sanders. “I would hope that a President as intelligent as Mr. Clinton does not repeat the absurd economic dogma of Reaganomics.”

At the time, Sanders was a vocal opponent of the administration-backed North American Free Trade Agreement, which the House approved in November.

The Clintons’ less ambitious health care reform package finally died – thanks in large part to insurance industry opposition – in the summer of 1994, right before voters swept Newt Gingrich and Republicans into power in Congress.

Curry, who joined the administration after losing a bid for governor of Connecticut in that year’s wave election, said there was no whiff of Sanders’ influence with the Clintons by the time he arrived. “If Bernie was at the White House when I was there it would have been on a tour,” he said.

Sanders sat on the House Banking Committee and said at the Whitewater hearings that the episodes under investigation reflected “poor judgment” by the Clintons but that Congress should spend its time on more important issues. On the fourth day of hearings, he stormed out of the Capitol in frustration. He vocally opposed the House’s impeachment of Clinton in 1998, saying “while the president has behaved shamefully and deplorably, his actions do not rise to the level of an impeachable offense.”

With the moral support of the Heritage Foundation, Sanders led the bipartisan opposition in 1998 to the Clinton Administration’s plan to infuse the International Monetary Fund with $18 billion to bail out the economies hit by the 1997 Asian financial crisis, which Congress ultimately rejected. He also voted against the Financial Services Act of 1999, which passed and repealed the Glass-Steagall Act’s prohibition on mixing commercial banking, investment banking or insurance in a single institution.

By the time Sanders arrived in the Senate in 2007, Hillary Clinton was already gearing up for her first presidential run, though the two did find opportunities to join forces during their two-year overlap in the upper chamber. In 2007, they co-authored the Green Jobs Act, which funded renewable energy and energy efficiency programs and passed as part of a larger energy bill. They both served on the Health, Education, Labor and Pensions committee, and in July 2008, along with Barack Obama and Ted Kennedy, the pair co-sponsored the Access for All America Act to expand the availability of primary care medicine, which died in committee.

Now, even though it’s progressives in ascendance within the Democratic Party and Sanders maintains he’s running for the nomination to win, not just to influence the front-runner, he again finds himself in the familiar position of pushing Hillary Clinton to the left.

Sanders’ confidants say he’s always been impressed by the intelligence of both Clintons, and he continues to publicly profess good will for Hillary. “Maybe I shouldn’t say this: I like Hillary Clinton,” he said on CNN last month.

“He’s always admired Hillary,” said Huck Gutman, an adviser to Sanders in the early ’90s. “They’re modest friends.”

Sanders has insisted that if he loses the nomination that he won’t run against Clinton as a Ralph Nader-style spoiler in the general election. Nader himself, on the other hand, recently called Clinton “a menace to the United States.”

It’s an illustration of the extent to which the two political outsiders, once allies, have parted ways. Nader has known Sanders for decades and the Vermont socialist once referred to him as “a good friend” during a committee hearing, but he said Sanders hasn’t returned his phone calls for the past 15 years. During his time in Washington, as Sanders has fostered congenial relations with Clinton, said Nader, “He’s totally cut people like me out.”

Nader said he believes this reflects the pragmatism of both politicians more than any personal affinity. “The Clintons are very adept at expanding their alliances, so they’ve been very cordial throughout the years,” said Nader.

He said he wouldn’t go so far as to call the Sanders-Clinton relationship a friendship. “It’s more a mutual accommodation.”