On a Historic Meeting of Powerbrokers, Weeks Before Obama Took Office

Rahm Emanuel was so cold he could see his breath as he crossed the White House parking lot and entered the West Wing lobby. It was December 5, 2008, an unusually frigid morning in Washington, DC. But it wasn’t the weather that sent a chill through Emanuel; it was the unbelievably daunting challenge that lay ahead.

In just six weeks Emanuel would become White House chief of staff to Barack Obama, the 44th president of the United States. But for more than a month, he had watched in astonishment as the world they were about to inherit was turned upside down. The US economy was teetering on the edge of another Great Depression. Credit—the lifeblood of the world economy—was frozen. The entire auto industry was on the brink of collapse. Two bloody wars were mired in stalemate. There was more than a little truth, Emanuel thought, to the headline in The Onion: “Black Man Given Nation’s Worst Job.” The stiletto-tongued infighter, former senior adviser to Bill Clinton, and congressman from Illinois felt apprehensive. “I brought my pillow and my blankie,” he would later joke, looking back at that dark morning when the fate of the new administration seemed to hang in the balance. The truth was, Rahm Emanuel was scared.

The unannounced gathering at the White House that morning looked like a Cold War-era national security crisis. Black sedans and SUVs rolled up; men in dark suits clambered into the Executive Mansion. Emanuel thought about the elite fraternity that was assembling here: Donald Rumsfeld. Dick Cheney. Leon Panetta. Howard Baker Jr. Jack Watson. Ken Duberstein. John Sununu. Sam Skinner. Mack McLarty. John Podesta. Andrew Card. Joshua Bolten. They were among Washington’s most powerful figures of the last half century: secretaries of defense, OMB directors, governor, CIA director, majority leader, and vice president. But they had one thing above all in common. It was a special bond, a shared trial by fire that transcended their political differences: Every one of them had served as White House chief of staff.

As they gathered in the office they had all once occupied—now home to Joshua Bolten, George W. Bush’s current chief—they mingled and swapped stories. It had been Bolten’s idea to bring all the former White House chiefs together after the election, to give his successor advice on how to do the job. Bolten guessed that of the 13 other living chiefs, maybe a half dozen would actually show up. But to his amazement, only Reagan’s James Baker and Clinton’s Erskine Bowles were no-shows.

“It really was an amazing day,” recalls John Podesta, Clinton’s final chief, “because it was quite a collection of individuals: from Dick Cheney and Donald Rumsfeld to me and Rahm. The span of ideology and politics, the span of history was all very present. And we all got the chance to give Rahm one piece of advice.” Clinton’s gregarious former chief Leon Panetta, about to be tapped as Obama’s CIA director, was in his element: “All of them were my close friends,” he recalls. “And to have them together in that room to wish Rahm Emanuel the best in his entry into that rogues’ gallery of chiefs of staff—that was a very special moment.”

The ghosts of presidencies past hovered around them. “It’s a space where you feel the presence of history,” Bolten would recall. “They were all transported back to their time in office.”

Dick Cheney, once the 34-year-old chief of staff to President Gerald Ford, pointed to the spot on the floor where Federal Reserve chief Alan Greenspan, immobilized by a bad back, used to lie supine during meetings, declaiming on monetary and fiscal policy. A fire crackled in the corner fireplace below a magnificent oil portrait of Abraham Lincoln. Finally, Bolten called the gathering to order and herded his distinguished guests around a long table.

At opposite ends sat two men whose political fortunes had been linked for a generation: Cheney, who would be vice president for six more weeks; and Rumsfeld, who had resigned under fire as defense secretary. It was Rumsfeld who had taken Cheney under his wing as a young political science grad student in the Nixon White House—and then summoned him to serve as his deputy when he became Gerald Ford’s chief of staff. Together they had helped Ford cobble together his “accidental presidency” after the trauma of Watergate; they had also watched helplessly as South Vietnam was overrun by Communist forces, bringing a bloody and ignominious end to the longest war in US history. Thirty years later, during the Iraq War, Cheney, the protégé, would be called upon by George W. Bush to tell his mentor to step down as defense secretary. As the prime architects of another divisive conflict that was ending badly, Cheney and Rumsfeld had come full circle.

“It was a moment of bipartisanship that would seem almost inconceivable today, a throwback to a bygone era of civility.”

Cheney was impressed by the morning’s gathering. “This was unique in that you had all or nearly all of the living former chiefs of staff in the room at the same time,” he recalls. And the irony of giving advice to Barack Obama’s top adviser was not lost on him: “Obama had spent the better part of his campaign trashing us from one end of the country to the other. But he’s our president. By that stage he’d won the election. And when you’re all sitting around the table and getting ready to say, ‘Here are the keys to the men’s room,’ you really do want to take advantage of the opportunity to say, ‘Look, here’s a couple of things that you really need to keep in mind.’ ”

Presidential transitions are awkward, and Cheney had been through his share. “There’s always a certain amount of hubris involved for the new crowd coming in: ‘Well, if you guys are so smart, why did we beat you?’ And so it can get a little tense at times, but you’ve got to overcome those things, because there aren’t very many people who’ve run the White House. And there are valuable lessons to be learned. You really do want to try to equip the new guy with whatever wisdom you’ve acquired during the course of your time in office.”

It was a moment of bipartisanship that would seem almost inconceivable today, a throwback to a bygone era of civility. “There was a sense in that room,” says Podesta, “among Republicans and Democrats, that the country needed people to get together and find some leadership.” Even the notoriously partisan Emanuel gave his Republican counterparts the benefit of the doubt. “I think they knew how difficult this moment in time was historically,” he recalls. “I think everyone was wishing the administration well.” He did something few had ever seen him do before: He pulled out a pen and started to take notes.

Going around the table, one at a time, Bolten asked his guests to give the incoming chief their advice.

Fifty years of presidential history were represented, and no one knew that history better than Ken Duberstein. Cherubic and voluble, with a booming laugh, Brooklyn-born Duberstein had been Ronald Reagan’s final chief of staff, and the first Jew to hold the job. “President Reagan didn’t hire me for my good looks,” he liked to tell people. “He hired me because he knew that I would tell him straight—because that is the Brooklyn way.” (After leaving the White House, he set up shop on Pennsylvania Avenue, offering strategic planning to corporate clients.) Technically, Duberstein had been chief for just seven months; in reality, with his mentor Howard Baker preoccupied with a family illness, Duberstein had been Reagan’s cochief for his last two years. Not just companies, but presidents consulted him, hoping the Reagan magic might rub off. And few told more dramatic stories about being a witness to presidential history. At the height of the Cold War, accompanying Reagan to a speech at West Berlin’s Brandenburg Gate, it was Duberstein who urged the president to ignore the objections of his State Department and deliver his iconic challenge to the Soviet Union: “Mr. Gorbachev, tear down this wall!”

Now, in another time of crisis, Duberstein spoke first. “Always remember,” he said, looking at Emanuel, “that when you open your mouth, it is not you but the president who is speaking.” Emanuel stared back at him. “Oh, shit!” he said.

The chiefs erupted in laughter. Next up was Jack Watson. Now 70, square-jawed and handsome, Watson looked like a movie star; that’s what Jimmy Carter thought when the charismatic young Atlanta lawyer rode out on his motorcycle to meet the future president at his peanut farm more than 40 years ago. As a young marine in an elite special operations unit, Watson had set an obstacle course record at Quantico that stood for more than 20 years; charming, earnest, and silver-tongued, he became a successful trial lawyer, and one of Carter’s trusted advisers during his 1976 presidential campaign. “Jack isn’t normal,” says one of his colleagues. “I mean, he was injected with the perfect serum. If you want to criticize him, he’s too good to be true.” Watson had been put in charge of Carter’s transition, and many believed he was a contender to become his White House chief of staff. But in a fateful decision that would hobble his presidency, Carter refused to appoint a chief. (Two and a half years later, Carter remedied that but then compounded his mistake by giving the job to a person who was unsuited to it, a brilliant but disorganized political strategist named Hamilton Jordan.) With less than eight months left in his term, Carter finally gave the job to Watson. In that brief period, Watson earned the respect of his peers for his keen grasp of the position—a job he likened to a “javelin catcher.” He looked at Rahm and smiled. “Never forget the extraordinary opportunity you’ve been given to serve, and the privilege and responsibility that it represents,” he said. “You are sitting next to the most powerful person in the world. Remember to value and appreciate that fact every single day you’re here.”

John Podesta, the head of Obama’s transition team, was next. Grandson of an Italian immigrant, son of a Chicago factory worker, Podesta had been bitten by the political bug as a college scholarship student back in 1970, when he volunteered for a Connecticut Senate campaign—and met a wonkish Yale Law School student named Bill Clinton. Decades later, in the Clinton White House, Podesta would succeed Erskine Bowles as chief of staff. In the throes of the Monica Lewinsky scandal, Podesta was so well known for his hair-trigger temper that it was said he had an evil twin named “Skippy.” But this morning he preached humility and patience. “You’ve got to slow down, and listen,” he said. “You’ve got a lot of smart people who are in that building with you. And you’ve got to resist the temptation to always have the answer. Slow down, listen. You’ll learn a lot and you’ll make better decisions.”

Thomas F. “Mack” McLarty, the Arkansas businessman who had been Bill Clinton’s first chief of staff, knew better than anyone just how unforgiving the job could be. Courtly and charming, “Mack the Nice,” as he was known, was liked by almost everyone in Washington. But he had been a stranger to Capitol Hill and unschooled in its bare-knuckled wars. After a year and a half, with Clinton’s agenda stymied and reelection in jeopardy, McLarty had agreed to step down as chief. But everyone in this room could empathize; they had all served at the whim of their presidents, and more than a few had been fired. Some thought McLarty was too kind, too gentlemanly for the job; if pressed, Mack might have agreed. “Try to keep some perspective about what you’re doing and try to maintain your humanity,” he told Rahm. “You don’t always succeed. We’re all human and we make mistakes. It starts with recognizing what a privilege it is to serve the president of the United States, but more importantly, the people of this country. Keep that in perspective and don’t let it get out of proportion with this regal title of ‘chief of staff.’”

McLarty’s admonition could have been aimed squarely at another man seated at the table, John Sununu. George H.W. Bush had picked the combative ex-governor of New Hampshire as his chief, hoping that Sununu’s domestic policy chops would complement his own foreign policy expertise. Sununu liked to tell people—with a wink—that he was “just a warm, fuzzy pussycat.” In fact, he flaunted his image as the president’s son of a bitch like a badge of honor. Arrogant and confrontational, Sununu antagonized Congress, the press corps, and the White House staff alike. Later, when he was caught using government limousines and planes for personal trips, few came to his defense. Sununu would resign under a cloud. “You have to create a firewall between the president and those who are clawing to see the president,” he told Rahm. “Even if it creates problems for the chief of staff. I was very good at creating problems for the chief of staff.”

Leon Panetta was probably the most popular person in the room. The son of Italian immigrants, jovial and outgoing, he was equally at home on his walnut farm in Monterey, California, and in the corridors of the West Wing. But as Bill Clinton’s second chief—replacing McLarty—Panetta had wielded an iron fist inside a velvet glove. When he arrived, Clinton’s presidency was on the ropes, his ambitious agenda threatened by fights over gays in the military, the Whitewater scandal, and other distractions. The damage was self-inflicted, caused by Clinton’s indiscipline and sloppy staff work. Panetta stepped in and brought discipline and focus to the White House—enabling Clinton to regain his traction and go on to win a second term. Now it was Panetta’s turn to tutor Obama’s incoming chief: “Always, always, be straight and honest with the president of the United States,” he said. “Always tell him what he may not want to hear—because frankly, a lot of people in the White House will always tell the president what he wants to hear.”

“Immediately pick your successor . . . And always remember: You are not indispensable.”

Andrew Card, Bolten’s predecessor, had set the modern record for longevity as chief: five years and three months under George W. Bush. Yet Card, who had served five presidents, was intimidated, almost awed, by the company this morning. “These were truly historic people who served during phenomenally historic times and it was quite compelling because they’re all very wise,” he would recall. When it came his turn, Card urged Rahm to protect the office of the presidency: “A lot of people aren’t interested in protecting the institution of the presidency, Article 2 in the Constitution. In fact, it’s under attack almost all the time from Article 1, which is Congress, and Article 3, the courts. And there really aren’t too many people at the White House that pay attention to that.”

Next, all eyes turned to Donald Rumsfeld. The pugnacious, suffer-no-fools architect of the Iraq invasion, George Bush’s embattled defense secretary had been asked to resign after the bungling of the occupation and the scandals at Abu Ghraib. Bolten, who had brought the chiefs together this morning, had been instrumental in Rumsfeld’s firing.

And yet, around this table Rumsfeld was respected for an earlier incarnation—as Gerald R. Ford’s remarkably effective chief of staff. In the aftermath of the biggest scandal in American history, with Ford plummeting in the polls after his pardon of Richard Nixon for Watergate crimes, Rumsfeld had put Ford’s presidency back on track. He had been a congressman and ambassador—and would become a corporate CEO and defense secretary (twice). But Rumsfeld insisted that being Ford’s White House chief was by far the toughest job he’d ever had: “It was like climbing into the cockpit of a crippled plane in flight and trying to land it safely.” Rumsfeld had pulled Ford’s presidency out of a nosedive.

One of Rumsfeld’s first acts as chief had been to appoint Cheney as his deputy. In an episode that would seal their friendship, Rumsfeld had prevented Cheney’s career from imploding. Faced with an FBI background check, Cheney confessed a secret: Out West, in his twenties, he had been arrested twice—and jailed—for drunk driving. Rumsfeld (with Ford’s blessing) stood by him. For men who decades later would become two of the most powerful and polarizing figures in American history, it was the beginning of a formidable alliance.

Rumsfeld, the wily veteran, turned to Emanuel. “Immediately pick your successor,” he told him. “And always remember: You are not indispensable.” Emanuel could not resist taking a swing at this verbal softball. “Is that true for secretaries of defense?” he cracked. A roar of laughter went around the table. Even Rumsfeld forced a smile.

Finally it was Cheney’s turn to speak. Over eight years, the vice president had richly earned his reputation as the Darth Vader of the Far Right, the unapologetic author of the war on terror. But many of the men around this table had known a different Cheney. Decades earlier, succeeding Rumsfeld as chief, he’d been one of the most popular figures in Washington, helping Gerald Ford return from the dead politically and very nearly defeat Jimmy Carter. In that earlier incarnation, Cheney had been known for his humility and uncanny ability to forge consensus; his Secret Service moniker was “Backseat.” This supposedly kinder, gentler Cheney also had a wicked sense of humor and a fondness for elaborate practical jokes. The press corps loved him. In the years since, the debate over “What in the world happened to Cheney?” had become almost a parlor game among the chiefs. One theory was that he had been transformed by his experience as the powerful CEO of Halliburton. Others thought he had gone to the dark side in the 1980s, running secret “continuity of government” exercises (war games that simulated nuclear Armageddon). The truth was, Cheney’s archconservative ideology was nothing new; he had always been “somewhere to the right of Genghis Khan,” as one Ford colleague put it. But Cheney’s worldview now seemed bleaker, his disposition darker. His close friend and colleague Brent Scowcroft, estranged from Cheney over the Iraq War, was convinced that his ex-friend’s brushes with mortality had changed him (Cheney suffered five heart attacks before his transplant in 2012). “That’s what a bad heart will do to a person,” Scowcroft told me. The Iraq War also triggered fierce arguments between Cheney and James Baker, his former colleague and hunting partner. But Cheney’s close friend David Hume Kennerly, Ford’s White House photographer, insists that his supposed transformation was nonsense. He may have a point: Back in the 1970s Cheney had taken a job aptitude test. His ideal career match? An undertaker.

Now the most powerful vice president in modern history, whose nickname was “Big Time,” looked up at Emanuel over his glasses. “At all costs,” he said gravely, “control your vice president.” The chiefs erupted in the last round of laughter for the day. Cheney flashed a crooked smile.

Following the meeting, the chiefs gathered outside Bolten’s office. Then they headed down the hall toward the Oval Office. Leading the way was Bolten, who would be chief for six more weeks. At the rear, grasping a cane and clinging to his ex-deputy Ken Duberstein, was Howard Baker Jr., now 83 and hobbled by Parkinson’s disease.

Waiting for them was George W. Bush. A presidency that had begun with one cataclysmic crisis, on September 11, 2001, was ending with another: the prospect of worldwide financial collapse. The personal toll it had taken on the president was apparent. A subdued Bush greeted them, with none of his trademark nicknames or quips. “I had seen and met President Bush many times,” recalls Podesta. “But I thought to myself that morning how much the wear and tear of that office was lined into his face. He really looked like he was ready to wrap it up.” The chiefs said their good-byes to the president and one another and departed.