Doug Band worked alongside Bill Clinton every day for nearly two decades, first as a body man and then as one of the primary architects of his lucrative and often-fraught post-presidency. Then came a seismic falling out with accusations of self-dealing and soap-opera-level psychodrama. Now, for the first time since leaving Clinton’s orbit, Band goes on the record about his days in Clintonworld.
Doug Band’s office at Teneo, the corporate advisory firm he cofounded, is decorated like a wing of the Bill Clinton presidential library. Framed photographs of the 42nd president adorn virtually every surface
except for windows overlooking the rush hour traffic crawling down Park Avenue. “A lot of these pictures are just about moments,” Band said one morning last winter as he showed me his collection. Band, a broad-shouldered man with dark eyes and prematurely graying hair, appeared in many of the pictures. There were photos of Band and Clinton playing golf with Barack Obama, posing backstage with Michael Jackson, and meeting North Korean dictator Kim Jong-Il. “Bill Clinton was my life for almost 20 years,” Band said.
Band was 22 when he landed an unpaid internship in the White House counsel’s office midway through Clinton’s first term. He served as Clinton’s “body man” during the second while earning a Georgetown law degree at night. On paper, the job is a glorified gofer, but Band leveraged the position to build a filial bond with the leader of the free world. When Clinton left office in January 2001, Band was one of the aides Clinton invited to go with him. Band took on a role that was equal parts fixer, gatekeeper, wingman, consigliere, and adopted son. (Officially, his title was counselor.) “They were with each other all the time,” said former Clinton chief of staff John Podesta, who first got to know Band in the Clinton White House.
Band virtually invented Clinton’s postpresidential life. He set up Clinton’s Harlem office, helped launch the Clinton Foundation, and created the Clinton Global Initiative (CGI), the annual Davos-style conference that Clinton hosted in New York. Band and Clinton circled the globe in a private jet with a Rat Pack of billionaires that included supermarket magnate Ron Burkle, movie producer Steve Bing, and, infamously, Jeffrey Epstein. Before Clinton had quadruple-bypass surgery in 2004, he dialed Band at the first sign of chest pains. There were years that Clinton spent more time with Band than with any other person—including Hillary and Chelsea.
But when I met Band last February, he hadn’t been in a room with Bill Clinton in nearly five years. He couldn’t remember the last time they had spoken. “I don’t want anything to do with that whole world,” Band said after we’d been talking for nearly an hour.
Band’s breakup with Clinton remains a subject of fascination and fierce debate in the Clinton diaspora. Some view the split as a father-son story gone awry. Others see it as a cautionary tale. Band mastered the dark arts of self-dealing, power brokering, and conflict-of-interest navigation that made Clinton’s postpresidency seem, at times, like one big money grab. Like his mentor, he grew fabulously wealthy doing it. Band drew multiple salaries from Clinton’s office, the foundation, and CGI. He also had a side deal with Burkle’s Yucaipa Companies. Even his path out of Clintonworld charted directly through Clintonworld. Teneo was essentially an arm of the Clinton Foundation in its early years. Band converted foundation donors to Teneo clients and encouraged Teneo clients to donate to the foundation. With all the dollars flying back and forth, it looked to Band’s critics like Band was cashing in on his boss’s Rolodex. In 2018, Band and his family purchased a $20 million Manhattan town house that once belonged to David Rockefeller and are in the midst of a multiyear renovation. Last year, Band and his partners sold a majority stake of Teneo to private equity firm CVC Capital at a reported valuation of $700 million.
Those critics include the Clintons themselves, who offered a caustic assessment of Band when asked for comment. “No staffer has ever used their role to serve their interests as much as Doug Band,” a Clinton family spokesperson told me. “For many years he was a valuable member of President Clinton’s team and supportive of Clinton Foundation programs. Until he wasn’t. He put the foundation at risk by leveraging a world-class philanthropy for his own financial gain. It’s as disappointing a story as it is a sad one and ultimately why Doug Band and the Clintons parted ways.”
But Band’s admirers argue that he has been unfairly maligned. They say Band built a philanthropy empire that raised nearly $70 billion to tackle the world’s thorniest problems, from lowering the cost of AIDS drugs in Africa to fighting climate change. CGI accelerated the trend of corporations committing to fund social change (or at least make it part of their PR campaigns). Instead, Band’s allies say he is the victim of a whisper campaign by Clintonworld rivals—Chelsea Clinton most of all—who were jealous of his favorite-son status and business success, which, they point out, has continued after he cut ties with the Clintons. “Doug’s made a lot of money. Was the Clinton connection helpful? One hundred percent. But it discounts how smart Doug is,” a Clinton donor said. The source was one of many Clintonworld insiders who would only speak on background. “The split is real and it is deep. There’s nothing in it for me to get in the middle of it,” a longtime Clinton adviser said, offering an explanation I heard echoed in my reporting.
As a rule, Band does not give interviews. “I prefer to remain invisible,” he told me. But over the past year, he opened up to Vanity Fair about his years in Clinton’s innermost circle. We spoke at a moment when Americans in general, and Democrats in particular, are wrestling with the 42nd president’s complicated legacy in profound ways. Clinton’s #MeToo history, his signing of the ’94 crime bill (backed by Joe Biden in the Senate) that ushered in an era of mass incarceration of Black and brown men, and a coziness with Wall Street in an age of extreme income inequality are being reexamined in a newly critical light. Clintonism was based on the baby boomer credo that you truly can have it all. The Trump era was a direct (if deeply hypocritical) reaction to the rules-don’t-apply M.O. that the Clintons have so often practiced on the national stage for three decades. Practically speaking, if not for the Clintons’ baggage, there would be no President Trump.
Band has been doing his own reckoning. During a series of wide-ranging conversations and email exchanges, he looked back on the highs and lows of his Clinton years with a mix of pride and affection, but also anger and resentment. His reflections were often raw and unfiltered, in the way an adult child might talk about unresolved issues with their parents. (They also tended to arrive with crystal-clear 20/20 hindsight.) At other times, Band sounded relieved to have moved on. “It was, in the end, the best thing that happened to and for me,” he said. “I was able to focus on my family, not theirs; my life, not his.”
I had been speaking to Band for months before he was ready to tell his story. For the first time since 2012—but really since 1992—there wasn’t a Clinton running for something. With the Clinton era sliding into history, Band wanted to add his account to the record. “What you and I have discussed is history but it’s an accurate reflection of it,” he said. “It may come off as hostile or angry, but it’s just the raw truth and facts of what transpired. I think that’s important for people to understand.”
On the morning of January 21, 2001, Band staggered bleary-eyed into the kitchen of Clinton’s tasteful Dutch colonial in Chappaqua, New York, to report for his first day as chief aide to America’s newest ex-president. Clinton kicked off his postpresidency at one of the lowest moments in his long public life: the 11th-hour pardon of fugitive financier Marc Rich. “No one wanted to be around Clinton. No one wanted to work for him. He was a pariah,” Band recalled. Clinton’s approval rating, 57 percent when he left office, plunged to 39 percent as the controversy raged. Making matters worse, Clinton had more than $10 million in legal bills left over from his impeachment and no real plan to make money beyond writing his memoirs and giving paid speeches.
With Hillary living primarily in Washington, a newly sworn in junior senator, and Chelsea studying abroad at Oxford, friends remember Clinton seemed depressed and lonely. “There was no one around. Doug was it,” said a former Clinton administration official. Band would listen to Clinton tell war stories late into the night as they played Clinton’s favorite card game, a variation of Hearts called Oh, Hell. Other times, Band would educate Clinton. “He was very out of touch with the world,” Band recalled. “He asked me one night to explain what was going on in this show called Friends.”
An irony of their bond is that Band doesn’t consider himself a passionate Democrat. He grew up the youngest of four brothers in a Republican household in Sarasota, Florida. Band’s father was a wealthy real estate developer and helped Band score his first job in Washington: an internship for GOP congressman Dan Miller. Band told me he voted for John McCain in 2008 and Mitt Romney in 2012. (He wouldn’t tell me who he voted for in 2016 and 2020.)
Band considered working for Goldman Sachs after leaving the White House, but he ultimately saw Clinton as the more exciting entrepreneurial challenge. Band thought of himself as a management consultant rescuing a troubled company, or more accurately, a talent manager reviving the stalled career of a fading star. “He just showed up and did what I told him to do. That was why it worked so well for a decade,” Band said.
The turnaround plan started with a brokered cease-fire with members of the “vast right-wing conspiracy.” Band arranged private lunches between Clinton and Richard Mellon Scaife, David Koch, Rupert Murdoch, and Roger Ailes, among others. “Doug called me and said, ‘Hey, let’s try and find some common ground,’ ” recalled Chris Ruddy, who in 1997 published a book that speculated White House lawyer and Clinton friend Vince Foster was murdered. “We had lunch with Clinton in Harlem. It was supposed to be an hour and it ended up going almost three hours.”
Band’s ultimate goal was to transform Clinton from a beleaguered politician, remembered for sex scandals and debating what the meaning of the word is is, into the world’s philanthropist in chief. Band came up with the concept at the 2003 World Economic Forum as he watched attendees flock to Clinton like groupies. In 2005, Band convinced Clinton to host his own version of Davos. Celebrities, billionaires, and CEOs descended on New York to mix and mingle while making “pledges” to donate to charity. The Clinton Global Initiative quickly established itself as one of the hottest tickets on the conference circuit. In 2007, Gallup ranked Clinton’s favorability at 63 percent. “Clinton was happy because CGI gave him what he wanted–redemption and being in the spotlight,” Band said.
As the impresario of CGI, Band became a central node in a network of the most powerful people on the planet. Because Clinton didn’t carry a cell phone or use email, anyone who wanted to speak to Clinton had to go through Band. (At his peak, Band carried three BlackBerries at all times.) Most petitioners didn’t get through the door. Not surprisingly, this pissed off a lot of people. “You make so many enemies when you’re the right-hand guy to a powerful person. You just can’t make everyone happy,” Ruddy said. Band didn’t help himself by coming across to many as self-important and blunt. “You had to kiss Doug’s ass to get anywhere. It was like Doug began to think he was Bill Clinton,” said a Clinton adviser who dealt frequently with Band. Clinton ignored Band’s critics because Band was getting results.
Band’s relationship with Clinton rocketed Band into the stratosphere of Manhattan’s social scene. He frequented Bungalow 8 and Buddakan, and briefly dated Naomi Campbell. Band’s bachelor years ended when he met Lily Rafii, a Morgan Stanley banker turned handbag designer, at a Bergdorf’s trunk show. In 2007, they wed at the 17th-century Château de Vaux-le-Vicomte, near Paris, at a ceremony attended by no fewer than three billionaires. Clinton delivered a moving toast. “If there is one person I want in a foxhole with me, it’s Doug,” Band recalled Clinton saying.
His problem was that someone else was already in the foxhole.
Politics is the Clinton family business, and it was inevitable that Band would get squeezed between Bill’s and Hillary’s competing ambitions and conflicting priorities. It’s hard to overstate how parallel Bill’s and Hillary’s lives had become by the 2000s. “It was separate worlds that had very little overlap,” Band said. Band was Bill’s guy, which meant he saw Hillary’s career as a threat. “I wanted him to stay out of politics and do great big things,” Band said.
As Hillary’s 2008 run approached, the tensions played out, and the campaign brought on unwelcome scrutiny of Bill’s postpresidency. How exactly had Bill, with Band’s help, earned that $109 million after leaving office? The Wall Street Journal uncovered Band’s role in brokering a $100 million real estate deal between Italian con artist Raffaello Follieri, Ron Burkle, and a Clinton Foundation donor named Michael Cooper. (Follieri wired Band a $200,000 finder’s fee, which Band later returned.) A New York Times investigation exposed how Canadian mining mogul Frank Giustra won a lucrative uranium mining concession in Kazakhstan two days after Giustra and Bill dined with Kazakhstan’s strongman president. (Months later, Giustra donated $31 million to the Clinton Foundation and pledged $100 million more.)
Meanwhile, Bill’s erratic behavior during the 2008 Democratic primary torched his statesman image. “He dismantled everything we had done,” Band said. Bill took on the role of Hillary’s attack dog and went aggressively after Barack Obama. As the primary dragged on, Bill shouted at voters and reporters in a series of rope-line meltdowns. The spectacle of a former president denigrating America’s would-be first Black president went viral. Prominent Democrats called the outbursts “bizarre,” “ill-tempered,” and “ill-founded.” Al Sharpton said Bill needed to “shut up.”
At the time, Band attributed Bill’s mistakes to aftereffects of his 2004 heart attack, rustiness from not having run a national campaign in over a decade, and a visceral dislike of Hillary’s opponent. “Obama drove him nuts,” Band said. Looking back, however, Band thinks Bill may have consciously or unconsciously not wanted Hillary to win. “He was used to it being all about him, and if she won, it would be all about her. That’s not how he lived his life for the four decades leading up to that election,” he said. “In her White House, he would be back under a microscope but without the benefit of being the one in charge.” A Clinton spokesperson said: “That’s ridiculous. President Clinton did more than 300 events on her behalf, and very much wanted her to win.”
Hillary’s team faulted Band for failing to rein in his boss. “The view was Band was an enabler of Bill’s behavior,” a Hillary adviser told me. It’s a critique that still grates. “The idea that anyone can control a person, especially a former president of the United States, is completely ridiculous,” Band said.
When Obama offered Hillary the chance to be America’s chief diplomat that November, Band was thrilled. The job of secretary of state has historically been the most prestigious and apolitical of Cabinet appointments (at least prior to the Trump administration). Hillary’s post would allow Band to put politics behind, refocus Bill on philanthropy, and start the long process of repairing his reputation. But Hillary didn’t want to work for Obama. “She wasn’t over the primary loss,” Band remembered. During a phone call Band was present for, Hillary told Obama she was turning down the offer and would be issuing a press release stating so. “She was bitter, angry, and believed he didn’t deserve to be president,” Band recalled. With Bill’s help, Band implored Hillary to reconsider. “Over the next 12 or so hours she came around.”
In his new memoir, Obama recalls Hillary rebuffing his first offer 10 days after the election and then a late-night call on which she told him she was “still inclined to turn me down.” But he adds more context: Hillary was tired and wanted to get back to the Senate, he writes, and she was thinking of Bill and the foundation.
“Doug was never an adviser to nor counseled Secretary Clinton,” a Clinton family spokesperson said.
Whatever its origins, Hillary’s tenure at the State Department didn’t work out the way Band intended. The incoming administration, navigating uncharted territory when it came to an ex-president’s proximity to the State Department, imposed strict limits on Bill’s outside activities. John Podesta, who headed the Obama transition team, told Band that Bill would have to abide by nine conditions, including agreeing to clear all international speaking engagements with the State Department, and to publicly disclose the Clinton Foundation’s more than 200,000 donors. Band believed Obama’s advisers wanted to punish Bill for his campaign attacks. “The Obama team wanted to control and neuter [Bill],” Band said, still frustrated a decade-plus later. “The absurdity of the demands was high. I didn’t care, but I did care about them hampering our global work helping people for their own selfish purposes.”
Podesta, the rare figure to move between Clinton and Obama circles, didn’t see it that way. “I thought it was good for the foundation and good for Obama,” he told me. “Otherwise people would have asked questions.”
By this point, Band had internalized the Clintonian mindset that profit and public service can be pursued in tandem. It made him unable, or unwilling, to accept the administration’s concern that foreign donors would contribute to the Clinton Foundation to influence U.S. foreign policy. With the big dog on a tight leash and the Clinton Global Initiative being scaled back, Band started to question whether working for Bill was worth it anymore. Then two Americans were arrested in North Korea.
The television journalist Lisa Ling called Band in July 2009 with a surreal invitation: Kim Jong-Il wanted Bill Clinton to visit Pyongyang. Ling’s sister Laura, a correspondent for Al Gore’s news channel Current TV, was being held prisoner with another journalist, Euna Lee. The pair had been apprehended that March while filming along the border with China. Ling told Band that the Obama administration was back channeling with the Swiss government to secure the women’s freedom, but the North Koreans had rejected offers from the U.S. to send former president Jimmy Carter or former U.N. ambassador Bill Richardson. Kim would only release the women if Bill Clinton went.
Hostage negotiation and high-stakes international fixer work had become something of a leitmotif of Clinton’s postpresidency, and Band was often along for the ride. In 2001, Clinton and Band lobbied Chinese president Jiang Zemin to release two dozen Navy servicemen after their American reconnaissance plane crash-landed on Hunain Island. A few years later, Band negotiated with Saif Gaddafi, the reform-minded son of the Libyan dictator Muammar Gaddafi, to honor a settlement compensating the families of Pan Am 103 bombing victims (Band was on his way to JFK airport to meet Saif in Paris when he got the call from Clinton about his chest pains). Band even got an audience with Muammar in a tent in Tripoli. “He seemed like a crazy person,” Band told me.
Clinton deputized Band to plan their mission to North Korea, which was kept top secret. Officially, the U.S. government wasn’t even involved. Band called movie producer and Democratic mega-donor Steve Bing, who was in Havana attending a Cuban film awards event, and asked to borrow his 737. “I said, ‘Steve, we need your plane. I can’t tell you where we’re going and I need it next week.’ And he said, ‘What time and what airport do you need it at?’ ” Band recalled. Obama officials instructed Band not to pay bribes, but he withdrew $100,000 cash from his bank account and packed it in a duffel just in case.
Everything was set but, according to Band, Obama wouldn’t give the green light. “It was still early on in the Obama administration and feelings were still quite raw,” Band recalled. Every aspect of the mission turned into a tense negotiation. For instance, Obama wanted Clinton on the ground for no more than 20 hours, but the North Koreans insisted on an overnight stay, Band recalled. “The Obama folks were incredibly worried about Clinton going off script,” Band said, which was understandable given Clinton’s foot-in-mouth episodes on the campaign trail. Obama finally agreed to an overnight trip if Podesta went as the new president’s eyes and ears. “They sent Podesta to babysit Clinton while I was to get the hostages released and on that plane to get home,” Band said. Band and Clinton departed for North Korea on August 2.
Tensions between Band and the Obama administration flared throughout the trip. During a fuel stop in Japan, a State Department official told Band that Kim had been promised that the U.S. delegation would deliver a letter of gratitude from Obama, but the White House changed their minds, perhaps because they felt a letter would be seen as appeasing the nuclear-armed dictatorship. Band argued for Obama to reconsider. “They won’t do it, you have to go, good luck,” Band remembered the official saying.
On the tarmac in Pyongyang, Kim’s daughter, Kim Yo-jong, walked right past Clinton and demanded that Band turn over the nonexistent letter. “We want to see the hostages first,” Band told her, trying to buy time. Band had brought along his older brother Roger, who is a doctor, and they were allowed to evaluate the women’s medical condition. “For the next 20 hours, I did everything I could to make sure that they didn’t get upset that I didn’t have the letter,” Band recalled. “In their minds, that was part of the deal and we didn’t live up to our end of it. It was a mistake by the White House.”
At dinner, Kim Jong-Il invited Band and Clinton to attend a performance later in the evening. Band sensed a diplomatic trap. It would be a propaganda coup for the supreme leader to host Clinton at a mass rally of 100,000 North Koreans. As waiters brought out steaks and bottles of Château Latour, Kim kept bringing up the invitation, and Band kept declining. The circular conversation was like a scene out of Veep. “I knew he knew what I was saying when I kept saying Clinton was tired. I just kept saying it over and over,” Band recalled. Kim had to settle for a photograph of a stone-faced Clinton sitting in front of a mural of crashing waves by North Korean painter Kim Song-gun. Band is in the picture standing in the second row, right behind Kim.
With Ling’s and Lee’s freedom secured, the mission was shaping up to be a humanitarian and public relations triumph. But on the flight to California, Band learned from Lisa Ling that the White House didn’t want Clinton to deplane with the freed hostages in front of the cameras. Band saw it as the Obama administration’s petty way of denying Clinton a P.R. win. “It wasn’t lost on me what the moment would mean in terms of erasing all the dumb stuff Clinton did in the 2008 campaign,” Band recalled.
Band got on the phone with Denis McDonough at the National Security Council and told him Clinton would do what the White House wanted, but Band thought Obama was being ridiculous. “I’m saving you from yourself here,” Band recalled saying. “People are going to be like, ‘How small are you guys?’ ” Clinton got his photo op.
After North Korea, Band began to seriously think about moving on from Clintonworld. He was 36 and had been on the road 250 days a year for more than a decade. In December 2009, Band’s wife, Lily, gave birth to their first son five weeks early, which required a week in neonatal intensive care. “It was certainly a wake-up call as to what’s important,” Band remembered. There were other motivators at play as well. Working for Clinton was becoming less lucrative: Band’s outside consulting job with Ron Burkle was winding down.
Band wagered he could replicate the work he did for Clinton on a bigger scale, especially in an era of increased appetite for “corporate responsibility”-type public relations. His pitch was that CEOs would pay handsomely to have a strategic counselor on call. In 2010, Band partnered with a pair of P.R. executives named Declan Kelly and Paul Keary to found Teneo (“I possess” in Latin). They aspired to create a communications firm, investment bank, and management consultancy all in one, with fees to match: Teneo’s retainers would start at $150,000 a month and reach into the millions.
Band and Clinton had a long and difficult conversation when Band announced he was leaving. Loyalty is one of the virtues Clinton prizes most, and as a sign of respect, Band said he proposed a soft break that would, not insignificantly, allow him to remain on the board of CGI, which was attended by exactly the kind of client his new firm planned to sell. Band would remain involved in CGI and pay Clinton $2.5 million to sit on Teneo’s advisory board. Friends in Clintonworld warned Band he was creating too many conflicts of interest. “I told Doug, ‘You can be fish or you can be fowl. You can’t be both,’ ” Podesta recalled.
Band’s departure coincided with the emergence of a powerful new vector in Clintonworld. In the spring of 2011, Chelsea Clinton, then 31, became vice chairman of what would be the renamed Bill, Hillary, and Chelsea Clinton Foundation. After a peripatetic career that included stints at McKinsey, a hedge fund, and NBC News, it was as if she had finally claimed her birthright as heir to the family dynasty.
Initially, Band wasn’t threatened by Chelsea’s new role. Separated by seven years, they related to each other almost like half siblings. When Chelsea was in her 20s, Band helped get her concert tickets and restaurant reservations. Once, Band sent a letter to the owner of Osso Bucco on Chelsea’s behalf demanding the Manhattan restaurant take down a photo of Chelsea displayed out front. “While she may have dined at your restaurant, this does not serve as an endorsement,” Band wrote on Clinton letterhead. (Owner Nino Selimaj declined the request.) In 2010, Chelsea sent Band an effusive Christmas card. “I love you and am thankful beyond words for all you have done and do for my father,” she wrote.
But in every family, rivalries and jealousies can fester. Clintonworld sources told me that Chelsea grew to resent Band. “Chelsea hated Doug because he was like a son to her father,” a Clinton friend said. Band took offense that Chelsea treated him at times like hired help. It was a combustible mix that was about to explode into personal grievance. “As a board member, Chelsea had a responsibility to ask questions about Foundation activities she didn’t understand or had reservation about. For some reason, Doug seemed to resent that,” a Clinton spokesperson said.
Around the time Band launched Teneo in June 2011, Chelsea summoned Band and his cofounder Declan Kelly to the Clinton office in Harlem. Band walked in to find Bill flanked by Chelsea and her husband, financier Marc Mezvinsky. According to Band, Chelsea said Band’s $2.5 million offer to put her dad on Teneo’s advisory board wasn’t enough. She wanted Band to give her and Mezvinsky an ownership position in Teneo. To Band, it felt like a shakedown. “I thought she was kidding or deeply sick,” he told me. Band looked across the table at Bill, but he sided with Chelsea. Band refused to give up an equity stake. The meeting ended badly. A Clinton family spokesperson denies that Chelsea asked for equity.
Over the next months, the conflict played out in Shakespearean terms, with Bill Clinton, the aging king, caught in the middle. Chelsea heard from foundation officials that Band was “hustling” donors to become Teneo clients behind Bill’s back. Band heard that she accused Band of planting a Page Six item about troubles in her marriage, which he denied. Band, meanwhile, told foundation staff that Chelsea was vastly underqualified to be in charge. He found it especially galling that Chelsea accused him of cashing in on his Clinton connections when, in his view, Chelsea benefited far more from her famous last name. He told people she got paid $1.2 million by NBC, not $600,000 as was reported. She had a driver, security, a $10 million apartment, a wedding that cost $5 million, and traveled on private planes. “Every job she received was based on her name,” Band said, still vexed. “Mine was based on my reputation, experience, and what I had done.” (A Clinton spokesperson denied Chelsea was paid $1.2 million by NBC.)
By the fall of 2011, the rivalry had turned into a war of attrition. Band looked for an advantage anywhere he could find one. The Clintons’ ties to Jeffrey Epstein and Ghislaine Maxwell provided one. Band told me he had been trying to push Epstein out of Clinton’s orbit ever since their much-discussed 2002 trip to Africa aboard Epstein’s private 727, dubbed the “Lolita Express.” Band recalled that Epstein had made a bunch of ridiculous claims on the trip, like boasting that he invented the derivatives market. Band said he had no idea about Epstein’s sex crimes back then but got enough bad vibes that he advised Clinton to end the relationship. But Clinton continued to socialize with Epstein and take his money. In 2006 Epstein donated $25,000 to the Clinton Foundation. Clinton made more than two dozen trips on Epstein’s jet around this time, Epstein’s flight logs show. In January 2003, according to Band, Clinton visited Epstein’s private Caribbean island, Little St. James. Band said it was one of the few trips he declined to go on in his time with Clinton. A Clinton spokesperson said the president had never been to the island and provided detailed travelogue entries of the period in question that did not contain a visit.
Chelsea had ties to Epstein and Maxwell, Band said; he showed me a photo of Bill and Chelsea posing with Epstein and Maxwell at the King of Morocco’s wedding. Chelsea remained friends with Maxwell for years after the press revealed Maxwell was a close associate of Epstein’s. For instance, Chelsea invited Maxwell to her 2010 wedding at the Brooke Astor estate in Rhinebeck, New York, after Epstein had pleaded guilty in Florida to procuring sex from a minor.
“Ghislaine had access to yachts and nice homes. Chelsea needed that,” Band told me.
A Clinton family spokesperson said Chelsea was on friendly terms with Maxwell because of a mutual friend (Gateway computer founder Ted Waitt) and only took one yacht trip with Maxwell in 2009: “It wasn’t until 2015 that Chelsea became aware of the horrific allegations against Ghislaine Maxwell and she hopes that all the victims find justice. Chelsea was friendly with her because of Maxwell’s relationship with a dear friend. When that relationship ended, Chelsea’s relationship with her ended as well.”
In late October 2011, Band instructed Bill Clinton’s office to bar Maxwell from all Clintonworld events as a way of driving a wedge between Maxwell and Chelsea. “I knew in telling everyone to stop including Ghislaine that Chelsea and her father would be very angry. It made it harder for them to justify being close to her,” Band said.
The Clinton Foundation retained the law firm Simpson Thacher to conduct an independent audit of the foundation, which Band saw as a pretext to investigate him. He had just launched Teneo and was worried that lawyers sniffing around could scare off potential clients, killing his new company in the crib. “I had already started my new life,” Band said. “She tried to shoot me, in the back, to justify her own power grab.”
A Clinton spokesperson said Chelsea wasn’t motivated by personal animosity: “Chelsea was concerned about Doug’s behavior and grew to distrust him.”
Band appealed to Clinton to intervene, but Clinton, famously conflict averse, stayed out. Finally, the Clintons’ longtime friend Terry McAuliffe offered to mediate. In December 2011, McAuliffe invited Band on a trip to the Middle East, where Clinton was giving a paid speech. The group gathered over dinner at the Burj hotel in Dubai to work everything out.
It had been nearly 10 years since Band started the postpresidential journey with Clinton, and a decade of pent-up emotions and resentments poured out of him in an airing of grievances that reached psychodrama proportions. Band told Clinton that he believed he was allowing Chelsea to destroy Band’s reputation because, deep down, Clinton was guilty for the pain his infidelities had caused the family. Then Band said the unsayable: If Clinton wanted to have girlfriends, he should divorce Hillary and move on with his life. Band later told friends he said it was the honorable and right thing to do. Clinton listened in cold silence, biting his lower lip. Band’s relationship with his mentor never was the same after the trip.
By 2015, Band had severed all ties to the Clintons. He thought he was free and clear. But he was soon sucked into the scandal gyre of Hillary’s 2016 presidential run. Republicans accused Band of attempting to buy access to the State Department after news broke that Band had given longtime Hillary aide Huma Abedin a job at Teneo while Abedin worked for Hillary at State. In one email, Band had written to Abedin to arrange a meeting at the State Department between Hillary and Bahrain’s Crown Prince Salman bin Hamad bin Isa al-Khalifa. The perception of conflict was impossible to miss, but Band told me he hired Abedin to give her the financial freedom to leave the Clintons—and her disgraced husband, Anthony Weiner—not because Band sought government favors. “I was so close to Huma for so long, and we had gone through so much together. I felt like I owed it to her to give her the gift of moving on,” he said. “But clearly it was a mistake.”
The low point came when reporters published Band’s emails during the breathless coverage of John Podesta’s hacked email account. Band’s feud with Chelsea was unspooled in a bunch of vivid exchanges. In one widely quoted email, Band called Chelsea a “spoiled brat kid.” “I thought so much of the behavior during WikiLeaks was so bad,” Band recalled. “If you take money out of someone’s bank account and use it or give it to others, that is a felony. If you take someone’s email from their account and use it and give it to others, it’s not.”
Band’s image needed rehab, and he got some help via the kind of moonlighting that only someone in his position could have developed. After the success of North Korea, Band had set out to become something of a statesman himself and became a freelance hostage negotiator. In 2014, Band asked the Obama administration for permission to lobby Fidel Castro to release a jailed 65-year-old American aid worker named Alan Gross on humanitarian grounds. (Gross lost more than 100 pounds and most of his teeth during five years in captivity.) Several months after Band’s trip, the Cubans released Gross in exchange for three Cuban spies held by the U.S. In 2018, Bill Gates asked Band if he could persuade Bahrain’s crown prince to release an American medical student named Billy Aziz, who was a close friend of Gates’s daughter. Aziz was serving a 10-year sentence in Bahrain for drug dealing; his family insists he was coerced into making a false confession. Band knew the crown prince well through the CGI conferences–Bahrain pledged $32 million to fund an educational partnership–so it only took a few phone calls to arrange a meeting between Gates and Bahrain’s ambassador to the U.S. Band made several trips to the Middle East to lobby the Bahrainis and Saudi Arabia’s Crown Prince Mohammed Bin Salman, who had vast influence in Bahrain. A few months after Band got involved, the Bahrainis put Aziz on a British Airways flight to London, where Gates’s private jet was waiting to take him home.
Around Washington, Band was building a reputation as a fixer with high-level relationships all over the world. “Having seen Clinton at close range and other world leaders, you’re a student of how these people operate,” Band told me. Yet the work would lead to the surest signal that Band’s evolution from Clinton acolyte to apostate was complete. In September 2019, Band secretly met with Secretary of State Mike Pompeo to discuss going to work for the Trump administration as the U.S. government’s chief hostage negotiator. “I knew I would get crucified, but it didn’t matter,” Band told me. “If your sister was taken hostage, who cares who the president is? I don’t think it’s a partisan issue.” In the end, he didn’t accept the job, but not because he had qualms about working for Trump. With four children at home and the pressures of managing 800 employees at Teneo, Band couldn’t afford to be away for prolonged stretches.
But the fact that Band seriously considered working for an administration that locked children in cages is a microcosm of the Clintonian value system, in all of its moral and ethical contradictions. The postpresidency Band designed for Clinton operated on the unspoken premise that there is nothing wrong with self-dealing or sketchy relationships as long as they’re in service of beneficent ends. “When you are trying to raise large sums of money to do great, big, and helpful things for the world, you have to make choices,” Band said. “There are lines people draw, and sometimes they get close to them or go over.”
But in an age of appalling income inequality, this way of thinking looks like corruption to a lot of people. It’s how Trump’s 2016 campaign successfully defined Hillary as a member of the globalist oligarchy that Trump claimed he would dismantle. (Never mind that Trump governed in the style of a petro dictator who oversaw a grotesque wealth transfer to the rich, obscene cronyism, and outright criminality.) At a basic level, Trump’s frame of the Clintons resonated. It’s also why Trump ultimately failed to run the same playbook against Joe Biden. The 2020 election ended the Clinton era.
These days, friends give Band periodic updates about his former boss. Mostly, the news isn’t good. Clinton has largely retreated from public life, though not necessarily by choice. Democrats are abandoning him as the media uncovers new details about his ties to Epstein and Maxwell. A few hours before Clinton was scheduled to speak at the Democratic National Convention, on August 18, the Daily Mail published previously unseen photos from the 2002 trip to Africa with Epstein. In one, Clinton slouches in an airport chair grinning boyishly as a 22-year-old blond masseuse named Chauntae Davies works on his shoulders (Davies accused Epstein of raping her numerous times during a four-year period). The Biden campaign allotted just five minutes for Clinton’s taped convention address that none of the networks carried live. Band told me he didn’t watch.
I recently asked Band if he thought he would ever reconcile with Clinton. “I will always be enormously grateful for the opportunity to serve, have great respect for his impact on the world, and have enormous personal affinity towards him,” he said. “We will always have shared a certain amount of life together that only he and I can or will ever understand. I harbor no negative feelings or anger towards him whatsoever.”
The years apart, though, have given Band clarity about what his life was for so many years. “It’s like a cult, that world,” he said. “It’s hard to get yourself out and difficult to see outside of it. And it’s even harder to understand that when you’re inside.”