The candidate who pivoted from first lady to Senate candidate overcame big odds. | AP Photos A model for Clinton '16: Clinton 2000

The most urgent question Hillary Clinton would face if she were to run again for president is whether she could avoid the blunders — the bitter staff rivalries going public, the poisonous relationship with the press, the presumption of inevitability — that helped doom her campaign five years ago.

There’s one powerful piece of evidence that she could — her own bid for New York senator in 2000.


The Clinton of 2008 — portrayed as a brittle, hardened caricature and a relic of an era of political triangulation that the country wanted to move past — bore little resemblance to the 2000 version. The candidate who pivoted from first lady to Senate candidate overcame a “carpetbagger” tag, ditched the Rose Garden strategy and campaigned hard in New York’s purple upstate region.

It’s easy to forget just how precarious a venture Clinton was embarking on back then. The Clintons were fresh from the impeachment battle. The first lady was one the most polarizing figures in the country, surrounded by an international media swarm. The early betting was she couldn’t break through the protective bubble of Secret Service agents and advisers to forge a meaningful connection with voters.

She did all of those things, handily beating Republican Rick Lazio.

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Granted, one was a statewide race in a Democratic state, the other a national campaign. She had a bigger margin for error in 2000 — especially after Rudy Giuliani spent a year barely campaigning before pulling the plug — than against Barack Obama.

But if Clinton runs again in 2016, she’ll have to answer the overriding criticism of 2008: that she ran as if the nomination were hers. Chief among her challenges would be hiring a new team that includes staffers who aren’t familiar to her; the way modern campaigns are run will require fresh blood.

Here’s a look at what Clinton did right in 2000, and how the lessons of that effort could help her if she were to run again in three years.

Letting go and staffing up

The tales of dysfunction from Clinton’s 2008 campaign are well-known, thanks in part to the book “Game Change.” The team was composed of people who’d worked with her over the years, but was led, to much criticism after the fact, by pollster Mark Penn.

Clinton allies know she will need new faces for 2016 — people who are empowered and trusted to do their jobs. It was one of the most important leaps of faith she took in 1999.

Some of it was out of necessity: Clinton was campaigning in a state she didn’t know, where tribal politics were difficult to navigate.

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When she arrived in New York, Clinton combined familiar advisers — admaker Mandy Grunwald, policy adviser Neera Tanden, advisers Mark Penn [whose role was dramatically expanded in 2008], Harold Ickes and Patti Solis Doyle, and aides Karen Finney and Kelly Craighead — with a large group of people she’d never met before.

They included Bill de Blasio, the current New York City mayoral front-runner, who was tapped to be her campaign manager; Howard Wolfson, the current deputy mayor under Michael Bloomberg who before 2000 had been chief of staff to Rep. Nita Lowey; press aide Karen Dunn, who last year was part of Obama’s presidential debate prep team; Jewish liaison Matthew Hiltzik; and, on the coordinated, soft-money campaign, operatives like David Axelrod, Sean Sweeney, later an Obama White House political hand; pollster Geoff Garin and former political strategist Gigi Georges.

As with other Clinton endeavors, factions emerged, and ultimately Solis Doyle took the reins of the campaign to drive it over the finish line. The campaign was messier than it appeared from the outside, but unlike 2008, it didn’t spill very openly into public view. But the clarity of purpose — getting Clinton elected — resembled what would happen during Obama’s 2008 campaign.

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“From the outset, people united to be part of something historic, and you felt it,” said one former campaign adviser. “It wasn’t just that she was the only first lady to run; there had never been a woman elected statewide in New York before.”

Trusting that a new team can both perform its job well and with her best interests at heart would be critical for Clinton next time around.

Earn it, don’t presume it

The biggest complaint about Clinton in 2008 was that she ran a campaign of entitlement, showing feistiness and emotion only after Obama had surged, when it was already too late.

Ahead in the polls at the outset, Clinton adopted a Rose Garden strategy for much of the first part of 2007. It was a far cry from her 2000 race.

Beset by “carpetbagger” criticisms, the first lady, who hailed from Illinois, began her campaign with a “listening tour,” a concept roundly mocked in the news media at the time.

It was not a strategy without risks. Clinton had tried to delay forming an exploratory committee as long as possible, but outside events — taunts from Giuliani’s team, Democrats in the state fretting she needed to begin campaigning — overtook her timetable. When she began the tour, she was widely seen as ill-prepared to talk about New York’s set of issues.

And there were plenty of mistakes: She was derided for wearing a Yankees cap and created an uproar for kissing Yasser Arafat’s wife, Suha, during an official White House trip. But the early initiation allowed her to get around the Empire State and make her mistakes early. What’s more, she was treated like a rock star, drowning out negative coverage. The cartoon version of Hillary Clinton — shrill, regal — largely evaporated.

Said another former adviser: “There was no arrogance [in Clinton’s campaign], there was no presumption that this was hers.”

In 2016, with Clinton’s persona larger than ever and no obvious Obama-like candidate in the wings, Clinton will have to summon her 2000-era self to show she’s working hard for the job.

Retail, retail, retail

Clinton barely engaged with Iowa voters in a meaningful way in 2007, a fact that came back to bite her when the better-organized Obama vaulted ahead. Voters complained throughout the race about a lack of access to the candidate.

In 2000, by contrast, Clinton made a point of visiting towns that had rarely, if ever, seen a Democratic statewide political candidate before.

Her aides were convinced the Midwestern-born Clinton would be able to compete in upstate New York.

“She let people really see her,” said Albany Mayor Jerry Jennings.

Clinton famously ate a sausage at the State Fair (Rick Lazio declined the offering), focused on her jobs plan for the economically depressed upstate region and sold herself as a get-the-job-done pol, not a partisan. Clinton loved traveling to all corners of the state in a van the press dubbed the “HRC Speedwagon” — and it showed.

Toward the end of the race, many of the attacks that Lazio and state Republicans lobbed at her rang hollow to voters — because they had gotten to know her.

The 2008 candidate never gave herself that chance, maintaining an ambivalent relationship with Iowa, where retail politics are at a premium. The 2000 campaign showed it need not be that way if Clinton were to run again.

Media matters

Clinton’s 2008 campaign has been derided as hostile toward the press, an attitude that was believed to have stemmed from the candidate herself.

Holding casual off-the-record meetings with reporters is something Clinton had done before, though never with the frequency of her Senate colleagues. But in the 2000 race, she was more willing to engage with reporters than she was during her first bid for president.

What’s more, the earlier Senate bid did not adopt the raise-the-drawbridge mentality of her 2008 team — a defensive posture that fueled a dynamic in which the news media collectively praised Obama while savaging Clinton.

“Her press operation — like her campaign — got better as it went along,” recalled Bob Hardt, the reporter assigned to Clinton by the New York Post who is now political director at the cable station NY1, of the 2000 run.

“One of the things that became apparent from covering her is that she has a real sense of humor,” he added. “She’d actually tease or joke with reporters on the trail. Her public persona is sometimes so guarded and scripted that her personality doesn’t come through.”

Clinton also benefited from running at a time when tweeting was something only birds did. She was less guarded, not having to fret that her every utterance would ricochet around the Web. The pace and tone of social media will be a challenge for Clinton, whose few posts so far on Twitter — comparing herself to swimmer Diana Nyad, for instance — have been the targets of some mockery. It remains to be seen if she can ever be at ease and have genuine interactions with people in the YouTube era.

There’s no question the 2016 media environment will be tougher to navigate than a statewide race a half-generation earlier. But Clinton need will need to recapture some of her earlier approach if she were to run again.

Dispelling the character fears

In 1999, Clinton did not have a problem on issues: Her views were aligned with the majority of New York Democrats. What she had was a character problem. People thought she had a sense of entitlement. They assumed she thought she could walk into the seat and that what she really had in mind was another job entirely: Even back then, the assumption among media elites was that what she wanted was to be president.

An entire strategy was devoted to humanizing her and convincing people that she was interested in the job. She went on David Letterman’s show in January 2000, striking up a relationship with him. She appeared on “Saturday Night Live” and poked fun at herself.

As it turned out, by the time she ran for reelection to the Senate in 2006, she was widely known to be preparing for a presidential campaign. The White House, people believed again, was what she’d had her sights on for years.

Clinton has a lot of work to do now to demonstrate she wants to be president for a larger purpose than, as Wall Street Journal columnist Peggy Noonan wrote last year of Mitt Romney, because “it’s the top job.”

Clinton gave some indication she’s aware she has to answer that question when she campaigned for Virginia Democratic gubernatorial hopeful Terry McAuliffe earlier this month.

“When you think about why people run for office in these times,” she told the crowd, “if it’s only about yourself, if it’s only about you wanting to get a job and the perks that go with it, and having people stand up when you come into the room, that’s not enough anymore, because it’s hard. Politics is hard.”

She would likely need a stronger answer, one demonstrated by deeds as much as words, in 2016. But her approach in New York 13 years ago could serve as a model.

CLARIFICATION: This report has been updated to reflect pollster Mark Penn’s role in 2000 and his expanded role in her 2008 presidential campaign.

CORRECTION: Corrected by: Alysha Love @ 10/28/2013 11:28 AM CLARIFICATION: This report has been updated to reflect pollster Mark Penn’s role in 2000 and his expanded role in her 2008 presidential campaign.