In September 1963, two months before his death, John F. Kennedy mused aloud to his old friend the journalist Charles Bartlett about the prospects for the 1968 presidential election, in which, he presciently worried, his brother Robert might run against Lyndon Johnson.

“He gave me the feeling he wasn’t pleased,” Bartlett would recall years later. “He wanted a record of his own. I sensed that he wanted the Kennedy administration to be Jack, and Bobby was going to turn it into a succession thing. Jack didn’t want a dynasty, although I am sure his father would have wanted that.”

Twenty-five years ago, Bill Clinton almost single-handedly repositioned the Democratic Party for electoral success, co-opting and defusing Republican talking points and moving the party toward the center on issues like welfare and a balanced budget, in the process becoming the first presidential nominee of his party since Franklin D. Roosevelt to win two consecutive terms. But even as he left office after the bitter 2000 recount, and George W. Bush returned the White House to Republican hands, there were questions about whether Clinton’s political philosophy would endure beyond his own tenure.

In 2008, Barack Obama explicitly campaigned against what he saw as the small-bore, one-from-column-A and two-from-column-B policy initiatives—school uniforms and the V-chip to block violence on television—of the Clinton years. Rejecting the political advice of his Clinton-era chief of staff, Rahm Emanuel, he swung for the fences instead, jammed health care reform through Congress on the narrowest of partisan votes, and paid a terrible political price, even while governing in most other ways as a pragmatic Clinton-style centrist.

What Bill and Hillary Clinton seemed to miss as they sought to burnish Bill’s legacy and build her a new one in this campaign was that the kind of “New Democrat” he’d once exemplified was now extinct, a victim first of Clinton’s own successes, and then of the economic and social dislocations of the globalism whose inevitability he foresaw when he predicted that Americans would one day “change jobs four or five times in their lifetimes!”

Bill Clinton’s “Third Way” ideology was also undone by sheer geopolitical realities—there are almost no Blue Dog Democrats left after a generation of redistricting, primary challenges and electoral defeats in the South—and by Obama’s cooler, more cerebral style of politics, which he deployed to defeat Hillary Clinton in 2008 as a strikingly fresh face.

By 2016, spurred by anger at Wall Street, and at Washington gridlock and business as usual, the Democratic Party had moved well to the left of the one Bill Clinton had inherited in 1992. And while Hillary Clinton recognized the change intellectually, she seemed unable to catch up to the practical realities of its political implications for her campaign. She embraced bold approaches on hot-button issues like immigration and gun control that would have been shocking for a Democrat in her husband’s day, and accepted what was arguably the most liberal Democratic Party platform in history, but that never seemed to be enough to satisfy younger voters, especially. “People thought she’d been conceived in Goldman Sachs’ trading desk,” says one veteran Clinton aide, noting the irony that this was millennial voters’ jaded view of a woman often seen in the 1990s as reflexively more liberal than her husband.

“Part of the problem is that there have just been lots and lots of changes in America in the past 25 years,” says Elaine Kamarck, who was a senior domestic policy adviser in Bill Clinton’s White House and is now a senior fellow at the Brookings Institution. “There were just a lot of cultural issues that were relevant for Bill that were gone by the time Hillary’s campaign came along, because by and large they’d been resolved or defused.”

Kamarck points in particular to the fraught politics of race and crime, a pair of linked issues to which Clinton, as a Southern Democrat, was acutely attuned—and at a time when memories of Republicans’ disemboweling of Michael Dukakis with the infamous Willie Horton ad, were still painful and fresh.

“A Democratic Party that was seen as more sympathetic to criminals than to victims was not a Democratic Party that was going to win elections. Bill Clinton had to correct that, and he did, and by 2015 we just did not have that kind of violent crime any more,” Kamarck says. The Clintons expressed regret for their 1990s posture, in light of declining crime rates, but Donald Trump still managed to paint the pair as somehow soft on crime, cherry-picking data on rising murder rates in cities like Chicago to claim that crime was “out of control” despite FBI statistics showing just the opposite was true overall.

To a journalist who covered the Clinton White House in the mid-1990s, the recent campaign’s emphasis on the 1994 crime bill’s call for harsh mandatory sentences, and Hillary Clinton’s contemporary warnings about criminals as “super-predators,” could seem jarring. The debate two decades ago was fully as much about whether the bill’s provisions for “community policing” and “midnight basketball” social service programs were too woolly-headed and soft-hearted. Somehow forgotten in the debate this year was Bill Clinton’s jiujitsu skill in parrying congressional Republicans to preserve his priorities—a phenomenon lamented by his former aides.

“People thought she’d been conceived in Goldman Sachs’ trading desk,” says one veteran Clinton aide.

“It is heartbreaking to have so many young people see him not as the guy who shut down the government to save the Great Society from Newt Gingrich,” says Gene Sperling, who headed Clinton’s national economic council, “but as somehow the guy who was the main mover of mandatory minimums, something that is not close to being the case.”

It has long been a commonplace that Hillary Clinton’s retail political skills are not the equal of her husband’s, and her senior advisers would chafe this year when Bill Clinton pressed to campaign more aggressively in white working-class areas of the Great American Middle, arguing that such voters had been lost for good by the Democrats—or at least for this year, during which disappointment over Obama’s inability to deliver for them had congealed into support for Trump. The truth is that Hillary Clinton did recognize the problem, even if she was unable to translate her awareness into an effective campaign message that would appeal to working-class whites.

After all, it was in the same speech to the elite Manhattan fundraiser where Clinton dismissed half of Trump’s supporters as a “basket of deplorables,” that she also said this, about the rest of his backers: “But the other basket—and I know this because I see friends from all over America here—people who feel that the government has let them down, the economy has let them down, nobody cares about them, nobody worries about what happens to their lives and their futures, and they’re just desperate for change. It doesn’t really even matter where it comes from,” Clinton said. “They don’t buy everything he says, but he seems to hold out some hope that their lives will be different—they won’t wake up and see their jobs disappear, lose a kid to heroin, feel like they’re in a dead end. Those are people we have to understand and empathize with as well.”

Driven by data that persuasively suggested she could never credibly present herself as the embodiment of change, and persuaded that her best shot at winning lay in painting Trump as so unstable and unqualified as to be unfit for the presidency, Clinton set aside the broader themes that had helped her husband win the White House in the first place.

“I just think if the Democrats are ever going to be able to come back and restore power, they’re going to have to pay attention to the working class,” says Leon Panetta, who served as Bill Clinton’s White House chief of staff and Obama’s CIA director and defense secretary. “I think Hillary got caught in the forest. To be able to be an effective candidate, you’ve got to be able to get out of the trees and see the forest for what it is.”

Panetta, whose late-career turn toward national security has overshadowed a keen political mind, thinks the surprisingly tough Democratic primary knocked the Clintons off kilter. “They had to deal with Bernie Sanders and the left. They had to make sure they retained that base, and they wanted to build on the Obama coalition that had gotten him elected and re-elected,” he told me. “And in that battle, they lost sight of the larger message she had to put across to the American people that she had her own version about where this country wanted to go, and that she, in her own way, represented change.”

Clinton was trapped, too, by her service as Obama’s secretary of state and her need to appeal to his winning coalition. She could not, or would not, say aloud what others in her party knew: That Obama had not only largely overlooked the concerns of white working-class voters but, with his health care overhaul, had been seen as punishing them financially to provide new benefits to the poorest Americans. Fairly or not, he lost the public argument.

The other truth is that a huge part of Clintonism was always Bill Clinton himself, and his singular ability to speak to both the most elite audiences and the most everyday ones in ways that could move each, with a unique combination of the Ozarks and Oxford that has rarely if ever been seen in contemporary American politics. Hillary Clinton’s best efforts to retail a retooled version of Clintonism in 2008 crumbled in the face of Obama’s promise of hope and change.

“Bill Clinton himself was Bubba,” as Kamarck puts it. “He always got that.” It was no accident that Clinton and Jimmy Carter—two white Southerners—stand as two of the only three Democrats to win the White House in the past half century (or that Obama had demographic advantages as an African-American that were not easily transferred to Hillary Clinton).

But Bill Clinton himself was far from an unalloyed asset in Hillary’s campaign this year. The rosy glow that had come to surround much of his post presidency, and his charitable foundation’s good works around the world, receded in the face of Trump’s relentless reminders of his personal and sexual misconduct in office, and his and his wife’s tendency toward legalistic corner-cutting—a point Sanders also drove home, even as he disavowed any interest in “her damn emails.”

“I think a lot of the problem for Hillary this time was that though Bill has kind of sustained a hold on the public’s imagination, and has a kind of charismatic quality that endears him to people and overshadows even his derring-do with Monica Lewinsky, it’s a mixed story,” says historian Robert Dallek. “The fact that you had someone like Trump who is so totally inexperienced gave him a considerable advantage.”

That advantage may have been a perverse one, given Trump’s own well-documented antediluvian conduct with women, but there is no arguing that Hillary’s campaign allowed her husband’s personal and policy legacy to be dragged back into the muck, at least in the short term.

“Because the campaign wanted to focus the debate on the future—and not a rehash of the 1990s—a certain amount of false caricatures were left unchallenged, which was unfortunate for him,” Sperling says. “You didn’t hear a lot of people putting in context that before Bill Clinton, Republicans had controlled the White House for 20 of 24 years, that his last six years in office were with an all-Republican Congress, or that the main reason he got crushed in 1994 was that he was perceived as being too progressive on health care.

“Do I think it will hurt Bill Clinton in the long run?” Sperling asks. “No, because he will still be most remembered for helping to bring about eight of the best years of shared growth and peace our country has had.”

Whatever the fate of Clintonism, the Democratic Party seems ready to move on; in a poll last week, 62 percent of Democrats and independents said they didn’t want Hillary Clinton to run again in 2020, a possibility that seems hard to fathom in any case. Fiery populists like Elizabeth Warren and Keith Ellison are vying to be the face of the opposition to Trump, whose early moves are already radicalizing Democrats to a degree unimaginable in the Clinton world of 1992, or even 1999.

Now Clinton’s time as the party’s Mr. Fix-It, and even as its “Explainer-in-Chief,” as Obama famously styled him, has ended for good. It will be left for someone in the next generation to build a new New Democratic coalition, one that can somehow rise above prevailing identity politics (much as Clinton did) to forge an interracial coalition of working-class voters who can carry the big swing states in the heart of the country that count in the Electoral College, and not just rack up a big popular vote advantage in the coastal cities. Whether that candidate is now as unknown as Barack Obama was just four years before he won the White House, or is hiding in plain sight in Congress or a statehouse or in a business on Wall Street or Main Street, the task will be the same as Bill Clinton’s was 25 years ago: to persuade the Democratic Party to stop making the same mistakes over and over and expecting a different result.