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Welcome to Hillaryland

A guide to the Clinton juggernaut.

LAST SUMMER, AS other potential 2008 presidential candidates were making their first sojourns to Iowa, Hillary Clinton did something a little different. She brought Iowa to Washington. In June, the senator, who is up for reelection this year but who has yet to draw a Republican challenger worth fretting about, entertained several key caucus-state activists and donors at her five-bedroom brick home on Embassy Row. Known to Hillary aides simply as Whitehaven, the 4,700-square-foot mansion is the site of the senator’s regular Washington fund-raisers and strategy sessions. Other 2008 contenders—Evan Bayh, Bill Richardson, John Edwards, John Kerry, and Mark Warner—have all recently introduced (or reintroduced) themselves to Iowans. Clinton introduced the Iowans to Hillaryland.    

Ever since 1992, when a young campaign staffer answered a phone call from Hillary with the greeting “Hillaryland,” the future first lady and her devoted, mostly female aides have embraced the cutesy sobriquet as a way to describe their unique, un-Bill (and sometimes anti-Bill) sorority. In the 1992 campaign, it described a small corner of office real estate in Little Rock where her staff toiled. In the Clinton White House, Hillaryland grew into an influential but often frustrated power center inhabited by dutiful staffers whose first allegiance was to the first lady, not the president. “[W]e were also our little subculture within the White House,” Hillary writes in her memoir. “My staff prided themselves on discretion, loyalty and camaraderie, and we had our own special ethos. While the West Wing had a tendency to leak, Hillaryland never did. While the president’s senior advisers jockeyed for big offices and proximity to the Oval Office, my senior staff happily shared offices with their young assistants.” Bill Clinton staffers regarded the dwellers in Hillaryland as Kool-Aid drinkers with awful political judgment. Hillarylanders saw Bill’s people as showboats and referred to them dismissively as the “white boys.” Hillary “took a dim view of many of her husband’s West Wing advisers,” writes John Harris in The Survivor, his excellent account of the Clinton years, “who she regarded as too immature and too worried about currying favor with the Washington press.” Hillaryland was different.

Today, Hillaryland is a vast political empire based in Washington and New York that, in its scale and ambition, is unrivaled in Democratic politics. But the spirit of Hillaryland, as well as many of its leaders, remains the same. Alan Patricof, Hillary’s Senate campaign finance chair, who has been raising money for the Clintons for two decades, says, “She’s got a very loyal group of people around her who have supported her for a long time.” In fact, everyone in Hillaryland says that. They prefer to compare Hillary’s operational style to George W. Bush’s rather than Bill’s. The unspoken, and sometimes spoken, premise is that, unlike her husband’s White House team—not to mention the last two Democratic presidential campaigns—there are no mercenaries in Hillaryland, only true believers, a culture they say is hardening now that many Democratic sharks are circling Hillaryland, looking for a way in. “I have been involved with her for seven years. [Advisers] Patti [Solis Doyle] and Maggie [Williams] are going on 15,” says one close adviser. “There is an intense loyalty.”

In Hillaryland, you’re either in or you’re out. Bill Clinton famously agonized over pushing aides from his inner circle. He cried and apologized the day his fired press secretary Dee Dee Myers left the White House. After the 1994 elections, he dawdled and couldn’t bring himself to get rid of several advisers who were left wondering about their status, even as he began to rely on their replacements. In contrast, Hillary’s team likes bright lines, and one way they maintain them is by firmly establishing an in-crowd. Joe Lockhart, the White House press secretary and face of the Clinton administration for two and a half years? Out. (They suspect he’s a John Edwards man, though an Edwards aide says he isn’t.) James Carville? In. (He’s personally close to Hillary and speaks to her regularly.) Doug Sosnik, one of Bill Clinton’s senior strategists in the late ’90s? Out. (He’s advising former Virginia Governor Mark Warner.) John Podesta, Clinton’s last chief of staff and now the president of the Center for American Progress? Way in. (He has important links to labor and environmental groups and serves as a policy conduit to Hillary.) Leon Panetta, Clinton’s second chief of staff? Far out. (He clashed with Hillary and tried to keep Hillaryland at arm’s length from the West Wing.) But trying to determine who’s in and out is nothing compared with figuring out who’s influential and who’s not. That search takes you deep into Hillaryland.

ONE DAY, I was walking down the street and bumped into a tier-one Hillary adviser. We gossiped about Hillaryland, and he cryptically suggested that Harold Ickes, one of the architects of Hillary’s 2000 Senate campaign and a devoted Hillary man, was no longer a key player. This seemed like big news. When Hillary first decided to run for Senate, it was Ickes who sat with her in the White House residence with a giant map of New York, explaining the challenges she faced. Hillaryland without Ickes is inconceivable. It turned out that the word on the street (literally) was wrong. It was some kind of complicated misdirection, something one often encounters in Hillaryland. Hillaryland experts offered me two contradictory explanations: Either my source was trying to sideline Ickes, an old White House rival, or protect Ickes, whose work with 527s requires him to maintain some distance from Hillaryland. But, for the record, Ickes is still an influential adviser.

As the case of the Ickes riddle shows, getting answers to simple questions is always a little harder in Hillaryland. Part of the problem is that there are so many power centers. For most senators, there’s only one—their Senate office. But, in Hillaryland, the Senate is just one outpost in a sprawling political organization. Says an adviser, straining not to offend Hillary’s Senate aides, “Let’s just say there are big and important players outside of the Senate office.”

The office is, however, an interesting microcosm of greater Hillaryland. It is relentlessly on-message and extremely wary of reporters. When I called the communications director to ask about the culture of the office and the backgrounds of its senior employees, she read me a staff directory. “Tamera Luzzatto is our chief of staff. ... Miguel Rodriguez is the counsel. ... Phillippe is the press secretary....” According to other denizens of Hillaryland, the Senate staff is especially tight-lipped because many aides don’t have longtime Hillary connections and realize that most of Hillary’s top strategists and advisers work elsewhere. “It’s a unique Senate staff, in that the main decisions don’t get made by the Senate staff,” says one Democrat. In fact, Hillary’s closest policy adviser, the highly regarded Neera Tanden, who has been with her for the better part of a decade, now works at the Center for American Progress. Luzzatto, the chief of staff, is a 20-year Senate veteran and is valued for her adept cloakroom politics, not her strategic or policy advice. “She does outreach to the groups,” says an adviser. “She doesn’t handle the legislation that much. She’s much more hands-on into the politics, the personal politics in the Senate, dealing with other senators.” If there’s a cultural divide in the office, Democrats say, it’s between worker-bee Senate aides and Hillary zealots. “When I came to the Senate office,“ says a longtime Hillary adviser, “I started throwing around `Hillaryland,’ and people looked at me like I was crazy.”

While the Senate office may not be Hillaryland’s nerve center, it is the public platform used to define the post-White House Hillary brand. And this ideological brand—and the people shaping it—are decidedly centrist. Consider, for example, Hillary’s new legislative director, Laurie Rubiner. The newest senior staffer in Hillaryland, Rubiner came to Hillary by way of former Republican Senators Lincoln Chaffee and Bob Dole and, most recently, the aggressively centrist New America Foundation, where she ran a program on universal health insurance. Her hiring says a lot about where Hillary is headed on the issues that may define a presidential campaign. Rubiner favors a universal plan, whereby the government mandates the purchase of health insurance, just as it does car insurance, from competing private providers, while subsidizing the neediest. Back in the ’90s, this was the centrist alternative to Hillarycare, and it was sponsored by Rubiner’s ex-bosses, Chaffee and Dole.

The Senate office has also been instrumental in executing Hillary’s high- profile campaign to co-sponsor legislation with practically every extremist Republican in the Senate. Her policy seems to be: The more right-wing the co- sponsor, the better; extra points for anyone involved with her husband’s impeachment. There was the legislation to ban flag-burning, co-sponsored with Utah’s Robert Bennett. There was the video game violence bill with Sam Brownback and Rick Santorum and the work on National Guard benefits with impeachment leader Lindsey Graham. Most of the issues on which she has allied herself with Republicans are symbolic, an effort to show, in the words of one senior adviser, that she’s “a little more socially conservative than people think.” This approach may also help her defuse future conservative criticism, something her Republican colleagues have belatedly come to realize. In fact, when I called the spokesmen of six of Hillary’s GOP co-sponsors, I couldn’t find a single one who criticized her commitment to the specific issue at hand, but most were decidedly uninterested in any more attention to their partnership. In one peculiar conversation, I negotiated a delicate agreement with a jittery GOP staffer to identify him only as a Republican and not by his boss’s name. I expected him to unload. “I gotta admit,” he said of Team Clinton, almost embarrassed, “they have been very good to work with. When they say they are going to do something, they do it! What more do you want? We worked really well with them.”

IF YOU REALLY want to understand Hillaryland, you have to look outside the Senate at the array of political machinery that runs and finances the Hillary empire. Between her own political and campaign committees and the fund-raising she has done for other Democrats, aides say that Hillary has raised some $50 million since 2001. In true Hillaryland fashion, the person who actually manages this expansive operation is almost unknown in political circles. She rarely talks to the press, save for an occasional anodyne quote about successful fund-raising numbers or one repeating how focused Hillary is on her Senate reelection, not the White House. She never appears on television. She declined to cooperate with this article. Her name is Patricia Solis Doyle— Patti to everyone in Hillaryland—and her job is running Hillary’s two main fund-raising entities, HillPAC, a so-called leadership committee, and Friends of Hillary (FOH), the senator’s reelection vehicle.

When Hillary advisers point out that, unlike the last three Democratic presidential candidates, Hillary is surrounded by longtime loyalists, they’re talking about people like Doyle, one of the crawl-across-broken-glass-for- Hillary friends, mostly women, who have been around a long time. Others in this camp are Maggie Williams, Hillary’s former East Wing chief of staff, who helps Doyle manage Hillaryland, and Tanden, a daughter of divorced Indian immigrants who credits government programs with saving her life and who has worshipped Hillary ever since she served as a nobody campaign staffer in 1992. Unlike Bill Clinton’s people, every Hillary lieutenant has a story of a personal favor or act of kindness their boss performed—a birthday party thrown at Whitehaven, a personal phone call during a rough time.

Doyle, the sixth child of Mexican parents who came to the United States illegally, is the president of this Hillary fan club. The first person Hillary hired for the 1992 campaign, she had the disarmingly simple title of “scheduler. “ Hillary has written that Doyle “ran my life hour by hour for nine years,“ and aides invariably describe her as one of Hillary’s closest confidantes, even if she’s not the most influential strategic and political adviser. “She’s the key person of the campaign,“ says Patricof, who hosts a monthly summit in New York of the Senate campaign’s top 100 fund-raisers and works closely with Doyle. “And she’s the interface. If I want to have a discussion about something of some significance, that’s the person I call.”

Doyle founded Hillaryland, and, 15 years later, she’s running it through her administration of the senator’s fund-raising arms, particularly HillPAC. After Hillary’s New York victory, HillPAC was the dominant political and fund-raising entity in Hillaryland, but, as 2006 approached, staff and energy gradually shifted from HillPAC to FOH, which is housed in the same K Street suite. Until the recent switch toward FOH, HillPAC had, in some ways, been the heart of Hillaryland. Ostensibly, its goal is to help elect other Democrats around the country. And, indeed, it has given a lot of money to other candidates and party committees—about $1 million in 2002 and about $500,000 in 2004. But that represents just 30 percent and 20 percent, respectively, of what the committee raised in those cycles. “In theory, a leadership PAC is designed to give money away,” says one Democratic campaign finance expert. “But they use the rest of it for political purposes. There are only so many candidates you can give money to.”

HillPAC, which is really the holding company for Hillary’s political machine, supplements the salaries of Hillary’s Senate staffers. It pays the consultants who write Hillary’s speeches for, say, a Gridiron dinner. It pays for the Beverly Hills firm Capital Strategies, which lassoes Hollywood money for Hillary. It pays about $5,000 a month to Hudson Media Partners, the political arm of the Glover Park Group, the powerhouse corporate consulting firm of Hillary’s top communications guru, Howard Wolfson. It writes checks to Occasions, the swanky Washington caterer that outfits Hillaryland events at Whitehaven. One of its largest expenses is to direct mail firms like O’Brien, McConnell & Pearson and Merkle Response Services, which are canvassing every nook of the United States for Hillary donors. By 2008, Hillary may have the most massive fund-raising database in politics.

Another key personality and loyalist involved with both HillPAC and FOH is Ann Lewis, a Clinton White House alum best known for her chipper TV punditry during the darkest days of ’90s-era scandals. A sort of Democratic Karen Hughes, she is so on-message that she recently left a voicemail for me concerning setting up interviews for this piece, but then launched into an unprompted critique of Bush’s State of the Union address. Lewis operates as a spokeswoman for Hillary, and she is also an ambassador to Democratic constituencies. She writes fund-raising e-mails and keeps an eye on Hillary’s relations with minorities and women. “Ann Lewis is much more an old-line Democrat,“ says a senior Hillary adviser. “She comes from the base.” As Hillary carves out an increasingly unambiguous centrist path, aides often point to Lewis as evidence of ideological diversity within the senior ranks of the campaign team. But one also gets the sense that this is partly her role—someone who gives Hillary credibility with liberals anxious about her recent moves. Not that they are trembling in Hillaryland over the fire from the left. The political bet is that, in a presidential campaign, the Democratic base of women, blacks, and labor can be won over in two ways: old-fashioned outreach and stroking by people like Lewis or by the sheer star power of Hillary Clinton.

WHILE THERE ARE plenty of lefties populating Hillaryland, especially in her circle of female confidantes, the spirit of the place is far from the communist salon imagined by the right. Read, for example, an excerpt of the mission statement of HillPAC, which is the closest thing in Hillaryland to her national platform:

We believe America must return to the path of fiscal responsibility that led to unprecedented prosperity during the 1990’s, helping to create more than 22 million new jobs and leading to historic, low levels of unemployment, inflation, crime, and interest rates and high levels of home ownership, access to education and productivity.
HILLPAC supports candidates who are working to restore investor confidence, ensure corporate accountability and protect workers’ pensions.

There are very few Democrats whose central message is about interest rates, crime, productivity, and investor confidence. And the ones who exist have been hounded into silence in recent years by the Internet left. Hang out in Hillaryland long enough and you realize it has embraced almost none of the hyperpartisan culture of the so-called netroots that many Democrats are chasing. And the makeup of Hillary’s core political consulting team suggests that’s not going to change.

When Howard Wolfson, Harold Ickes, Mandy Grunwald, and Mark Penn were thrown together six years ago, there was no reason to predict they would produce a twelve-point victory for Hillary in New York. Wolfson, the communications czar, had no previous experience in Hillaryland, but, as a local, he was liked—or at least feared—by the New York press. Ickes, the expert on New York state politics, had been unceremoniously dumped by Bill Clinton at the moment he thought he was going to be promoted to chief of staff (he read about it in the newspaper). Grunwald, the ad-maker and a 1992 campaign alum—that’s her voice yelling out of the speakerphone at James Carville in The War Room—was kicked out in 1995 to make room for the new team, which included none other than pollster Mark Penn. Penn, in turn, was brought in by Dick Morris, a man that Ickes has hated—“He’s a sleazy son of a bitch,“ he has said—for about 25 years, ever since they tangled in the politics of the Upper West Side.

These days, Hillaryland insiders like to compare the crew to Bush’s cohesive iron triangle of loyalists (Karl Rove, Joe Allbaugh, and Karen Hughes) who brought him from failed businessman to governor to president, but it didn’t look that way in 2000, when the campaign team devolved into two warring camps. According to Michael Tomasky’s insider account, Hillary’s Turn, a Hillaryland lifer, Susan Thomases, persuaded the first lady to add an edgy consultant, Dwight Jewson, to the team. The move sparked a war between Penn and Grunwald (who both wanted a laser-like focus on New York issues and who resented the presence of the new strategist) and Ickes and Jewson (who insisted on confronting character issues like the charge that Hillary was an opportunist). The war lasted four months, included a blockbuster New York Times magazine story based on a leaked Penn polling memo—an incident that turned the campaign into a fortress of secrecy—and generally almost sank Hillary. But, in the end, Penn and Grunwald, with their insistence on issues, no matter how small, won the internal battle and, of course, Hillary won the race.

Ever since then, Penn has been the messaging mastermind of Hillaryland. His stubborn centrism, arrived at by sifting through tons of granular-level psychographic polling—that is, psychological and demographic—has long angered liberals, and it is likely be the greatest source of future tension in Hillaryland. “We kind of know what Mark is going to say in every situation,” says one top adviser to his left. But there is little doubt that Hillary is a true devotee of Penn—who is also a Tony Blair adviser and partisan of the transatlantic Third Way project—and his middle-of-the-road style of politics.

Penn’s centrality to her political organization explains a lot about the political lessons Hillary has learned and the path she sees to the White House. Even as Hillary has rejected many Clintonites and the organizational style of their regime, she hasn’t rejected Clintonism. As her memoir makes clear, more than impeachment, the defining political moment in her life was the 1994 GOP takeover of the House, which devastated her. She was the one who brought Morris and Penn into the White House after that cataclysmic event, not her husband. She even defends Clinton’s much-maligned strategy of triangulation. “More than old-fashioned political compromise of splitting the difference,” she writes in her memoir, “triangulation reflected the approach Bill had promised to bring to Washington.” There was never any doubt that, after helping her husband win reelection and evolving into the most influential Clinton adviser of the second term, Penn would work for Hillary.

In the last six years, Hillary has built and held together a fearsome operation. She has rewarded longtime loyalists, while keeping doctrinaire old-timers on the payroll but at bay. She has pulled back into her orbit once- disaffected Clintonites whom she needs. In short, she has been ruthlessly pragmatic about who’s in and out in Hillaryland, handselecting specialists who could advance her political fortunes in specific areas. Penn proved himself as a “brilliant” (her word) strategist by reviving her husband’s presidency. Ickes knew New York politics. (If she had run in Illinois, she would have tapped Rahm Emanuel or some other prairie state Clintonite.) Her Senate chief of staff was hired for her special knowledge of the Byzantine chamber.

But she has also built a sprawling enterprise with competing power centers and ego-fueled senior aides with decades of rivalries and political baggage behind their resumes. And she has turned Hillaryland’s strategic steering wheel over to a pollster with a controversial view of how elections are won, which risks alienating many Democrats. Hillaryland will rise or fall on these two decisions.

My guess is the ideological tensions will be harder to overcome than the organizational ones. When I asked a senior adviser what Hillary’s toughest vote in the Senate was, this person immediately answered, “The war vote. It’s a big thing going to war.” The Iraq war divided Hillaryland. Tanden, for instance, vigorously opposed the war, while a faction of Democratic hawks inside and outside Hillaryland assured the senator of the conflict’s wisdom. Hillary is determined not to become tied in a pretzel by her pro-war vote, like John Kerry was. But there is evidence of some regret. In a private meeting with Ken Pollack, an aide says Hillary pointedly questioned the pro-war author: “Ken, you talked to me about weapons of mass destruction. What happened?” Some advisers now also highlight reservations she had. “I talked to her the day we invaded,” says one. “She said, ‘This could be very messy.’ She was very tortured that day. She was never gung ho.... She was thinking, ‘This could still go either way.’” The same thing could be said about Hillaryland.