This article is from the archive of our partner National Journal

In January of this year, a tantalizing piece of news surfaced about Jeb Bush, the strongest contender in the Republican Party's presidential nomination brawl. Bush, by delaying his official entrance into the race and maintaining the pretense that he wasn't yet a candidate for office, was seeking to raise $100 million in the early months of 2015, a number so large you'd be forgiven for thinking it was a typo. In the months that followed, Bush jetted around the country raising money at a torrid pace, most of it for an outfit called Right to Rise, a pro-Bush super PAC that—unlike his official campaign—could accept unlimited donations from individuals and corporations. The money poured in so fast that Bush's fundraisers asked people to limit themselves to $1 million or less, hoping to avoid tapping out their donors so early in the campaign. Bush's advisers dubbed it their "shock-and-awe" fundraising strategy; Mike Murphy, the longtime Bush confidant in charge of Right to Rise, told donors he planned to "weaponize" Bush's massive haul. By late April, Bush was crowing to a group of supporters that his operation had raised more money in 100 days than any other Republican committee in modern history.

Hillary Clinton followed the news of Bush's blitzkrieg with growing alarm. In response, a source inside the campaign told me, Clinton, who had declared her candidacy in mid-April, ratcheted up the rate of campaign fundraisers (which were legally obliged to observe a $2,700-a-head limit). But she also looked to the super PAC supporting her—Priorities USA Action—and found that, compared with Bush's outfit, its fundraising was anemic and showing few signs of picking up the pace.

Clinton's concerns filtered down through her campaign and into the pages of The New York Times—a clear signal to the Priorities staff. The timing wasn't good: Inside Priorities, frustrations were mounting. The super PAC's staff and board of directors, a mix of Clinton loyalists and Obama allies, were struggling to work together, donors were dismayed by leaks describing infighting at Priorities and tension with other Democratic groups, and Clinton loyalists were weighing options for replacing the group's Obama-aligned leadership with fresh blood. "It all sort of came to a head," a source close to the Clintons told me. "And when the chatter was that Hillary was wondering where the money was, that brought it to sharp relief."

Given its origins as a pro-Obama PAC, Priorities could serve as a way to show unity behind Clinton.

To some, it felt like echoes of Clinton's last presidential bid. Eight years ago, the universe of friends, allies, funders, and supplicants known as "Clintonworld" torpedoed Hillary's bid for the White House with clashing strategies, leaks to reporters, and factional struggles ("Even in Victory, Clinton Team Is Battling Itself," read one memorable headline in The Washington Post). To take just one example of the seemingly constant upheaval, Clinton's chief strategist, Mark Penn, resigned after it emerged that in his capacity as the CEO of an international PR and lobbying firm he'd met with a Colombian diplomat pushing for a new free-trade deal while Clinton herself was stumping on the campaign trail against the very same deal.

For 2016, Clinton has assembled a team, led by campaign manager Robby Mook and chairman John Podesta, intended to quell the worst elements of Clintonworld. Thus far, they appear to have succeeded. But like a game of Whac-a-Mole, some of the problems that plagued Clinton's last presidential run have resurfaced with her super PAC. And those problems appear to be both symptom and cause of the group's sluggish financial figures—just under $16 million raised in the first half of 2015, compared with $103 million for Bush's super PAC. As one Democratic fundraiser says of the Clintonworld drama, "It hasn't stopped—it's just moved to the outside."

IN EARLY 2011, two Obama aides, Bill Burton and Sean Sweeney, left the White House and launched Priorities USA Action with a single purpose: to reelect President Obama. It took nearly a year for a clearly ambivalent Obama to give his half-hearted blessing to the group, but once he did, Priorities built momentum and went on to raise around $90 million. Most of that money went toward casting Republican Mitt Romney as a cold-hearted vulture capitalist who in his business career had sacrificed the livelihoods of blue-collar workers to maximize profits. "If Mitt Romney wins, the middle class loses," went the tag line of Priorities' most memorable spot. The ads—and the group—ended up being a vital piece of Obama's reelection effort. Priorities also helped Democratic donors overcome their distaste for super PACs. "People appreciated that we did a good job and that we didn't have as much money as the Republican super PACs and got bang for their bucks," Burton told me. "We had a tangible impact on the national conversation."

After November 2012, it wasn't clear what should be done with the group. Disband? Find a new cause? Given the super PAC's track record, donors argued for keeping it around in some form, according to Burton. "Once we got to the end of the cycle and saw some measure of success, there was an assumption that [Priorities] was going to be an ongoing part of the Democratic infrastructure," he says. Jeffrey Katzenberg, the Hollywood mogul who provided $2 million in seed money for Priorities early on (and another $1 million closer to Election Day), was so bullish on the group that he suggested Priorities get involved in the 2014 congressional elections, according to a source who spoke with him at the time. But the idea was shot down.

Jim Messina (above) and Sean Sweeney-with the support of donors like Jeffrey Katzenberg and others-pushed to reinvent Priorities as the flagship Hillary Clinton super PAC. (Frank Polich/Getty Images)

In February 2013, Hillary Clinton formally resigned as secretary of State, the strongest signal yet that she planned to run for president in 2016. Any Clinton presidential run would, of course, need its own super PAC. According to a Priorities staffer from the 2012 campaign, Sweeney and Jim Messina (who'd run Obama's 2012 campaign) had watched dueling super PACs on the Republican side squander millions of dollars by running conflicting or duplicative ads as they sought to elect Mitt Romney. And so rather than start a new group from scratch, Messina and Sweeney, with the support of donors like Katzenberg and others, pushed to reinvent Priorities as the flagship Hillary Clinton super PAC and avoid repeating the Republican mess of 2012. Given its origins, Priorities could also serve as a way for the Obama and Clinton political factions to show unity behind a Clinton campaign. John Podesta, the former Clinton White House chief of staff, was briefly floated by Politico as a potential cochair for Priorities should Clinton run. Podesta instead took a job in the Obama White House, but the message was sent: Priorities was in Hillary's corner.

As it became increasingly clear that Clinton planned to run, Priorities unveiled its new look as a pro-Clinton super PAC. Buffy Wicks, a former Obama White House aide, was tapped to be executive director in January 2014. Wicks had little history with the Clintons and had climbed the Democratic ranks as a field organizer, working for Howard Dean's 2004 presidential bid and for Obama's 2008 and 2012 campaigns; but she was surrounded with senior advisers known by the Clintons and steeped in big-money fundraising. In addition to Sweeney, there was Jonathan Mantz, who was Clinton's 2008 finance director, and Diana Rogalle, who spearheaded Priorities' fundraising in the 2012 cycle. A new board of directors boasted as cochairs Messina and former Michigan Governor and Clinton booster Jennifer Granholm; other members included longtime Clinton allies Harold Ickes and Charlie Baker, Ready for Hillary cofounder Allida Black, EMILY's List President Stephanie Schriock, and Clinton antagonizer-turned-stalwart David Brock.

The New York Times story announcing Priorities' reinvention prominently featured Messina (for the time being, the super PAC rented office space from Messina's consulting shop); it also included a quote from one of the Democratic Party's biggest donors, Houston trial lawyer Steve Mostyn: "The Democrats are all cooperating," Mostyn said, "and the donors like it when they cooperate." All of this signaled to the party's wealthiest backers that Priorities was Clinton's super PAC, and everyone was on board. "It was a flag in the ground," an operative close to the Clintons told me. Another Democratic strategist saw it somewhat differently: "If you look at that front-page, above-the-fold, right-column New York Times article, one could conclude that Messina was anxious to get into the Hillary camp."

JUST AS QUICKLY as Priorities made its big January announcement, it went dark. Despite the excitement surrounding a potential Clinton presidential run, Priorities was sidelined for most of 2014. Any money it raised would have been effectively siphoned away from Democratic congressional campaigns. So Priorities agreed not to actively raise a penny during the '14 cycle. It donated $1.4 million of what it had left in the bank from two years earlier to 2014-focused groups such as the Democratic Governors Association. Wicks and her team waited until after the November elections to begin even the most preliminary conversations with potential donors.

Even with so little to do, board members and donors grew anxious with a perceived lack of activity inside the organization, singling out Messina and Sweeney for criticism. According to multiple sources close to Priorities, board members complained that Messina and Sweeney, the two nominal heads of Priorities, seemed disengaged, rarely attending or calling in for Priorities meetings.

Messina allies say his role with Priorities was misunderstood. His cochair position was an unpaid, volunteer, largely ceremonial role; he would bring the tech know-how and the donor network from Obama's 2012 run, which included a roster of Silicon Valley executives such as Google Executive Chairman Eric Schmidt, but he wouldn't play a hands-on role. "I don't think for a minute that Jim Messina ever saw himself working day-to-day in Priorities," says John Morgan, a prominent Orlando-based trial lawyer and donor who is close to Messina. (Messina declined to comment for this story; Sweeney referred my questions to a Priorities spokesman, who told me, "Sean has been fully engaged with this organization since day one.")

It didn't help that certain factions within Clintonworld viewed Messina with suspicion, and that Messina, two sources close to Priorities told me, did little to manage the internal machinations of the Clinton universe. Clinton allies respected him for his record as a political strategist but recoiled at the speed with which he had cashed in on his experience working for Obama, launching his own consulting firm and hitting the paid speaking circuit mere months after the 2012 election. (In one much-publicized instance, Messina pocketed five figures to speak at a conference held in Baku, the capital of Azerbaijan, which has faced heavy criticism for human-rights violations.) In August 2013, the BBC reported that Messina had taken on as a client the party of conservative British Prime Minister David Cameron, a move that rankled his fellow Democrats.

Ill will also lingered from Messina's time in the Obama White House, where he was seen as distancing the president from the progressive Left. For instance, George Soros, the philanthropist and financier, sought an audience with the president to discuss economic issues in the aftermath of the global financial crisis. He was rebuffed by Obama's staff. "They pissed on him," a Soros confidant told The New Yorker in 2012. Several sources told me that Soros was reluctant to give to Priorities while Messina was in charge. (A spokesman for Soros declined to comment.)

Donors feared—without evidence to back it up—that Messina would find ways to take a cut of the potentially huge sums of money flowing in and out of Priorities. The way the industry works, a super PAC like Priorities pays one set of consultants to create its TV and online ads and another set of consultants to buy airtime on which to run those ads. Sometimes, the creative types and the media buyers work at the same firm, and it's not unheard of for the higher-ups at such a firm to not only charge for crafting a client's latest attack ad but also take a cut of the ad buy itself—say, 10 percent of a $1 million purchase of airtime in a battleground state. Messina's defenders say that he has never and will never earn a penny at Priorities. A source who's worked with Messina likened the suspicions surrounding him to the way Karl Rove was viewed during the George W. Bush years. " 'Oh, Karl Rove's controlling everything,' " the source says, reciting a common refrain from the 2000s. "Now it's, 'Oh, Messina's controlling Priorities.' "

Worries over wasted funds festered after a New York Times story in February revealed the practice of political fundraisers taking a percentage of the money they raise. In this case, the Times described how Mary Pat Bonner, a fundraising consultant closely aligned with David Brock, took a 12.5 percent commission on donations she brought in, a practice that infuriated some major donors. The story caused a firestorm within Democratic circles. Brock, who was never fully accepted into the fold by the Obama camp, fired off an angry letter accusing "current and former Priorities officials" of "an orchestrated political hit job" and announcing his resignation from the Priorities board. (A Priorities spokesman denied that the group had any involvement in leaking the Times story.)

In an effort to assuage donors' concerns about how their money would be spent, Wicks drafted a set of transparency rules. According to four sources with knowledge of the measures, Wicks sought to prohibit any Priorities fundraiser from taking a commission; mid-level fundraisers would be paid a retainer that maxed out at $7,500 a month. Wicks also proposed banning anyone working for Priorities or serving on the board from taking a back-door cut of the group's ad buys. The aim, according to one source close to the Clintons, "was trying to ensure donor money was spent with transparency and that Priorities wasn't a money-making endeavor."

Wicks, however, barely got to see her ideas put into action. A May 20 story in The Wall Street Journal, titled "Hillary Clinton Super PAC Struggles to Raise Money," reported that Wicks and her team were on track to collect $15 million through the end of June. In Wicks's defense, it was a not-insignificant sum, given that Priorities didn't start fundraising in earnest until after Clinton had entered the race in April. But it paled in comparison with Jeb Bush's haul, and with the $31 million reportedly raised by a group of super PACs backing Ted Cruz. The Journal story quoted several anonymous sources describing "unhappiness" and "dissatisfaction" with Priorities' efforts. Well-liked and respected by many in Democratic circles, Wicks was nevertheless deemed the wrong person for the job and pushed aside to make room for someone tighter with the Clintons.

By the end of May, Wicks was out and Guy Cecil—a 41-year-old Democratic operative who'd lost out to Robby Mook for the job of managing Clinton's 2016 campaign—was in. Unlike Wicks, Cecil had worked for Clinton, acting as her political director during the 2008 run. More recently, he ran the Democratic Senatorial Campaign Committee in the 2012 and 2014 cycles. In an interview, Cecil told me that it was Sweeney who approached him about joining Priorities. By bringing him aboard, Cecil says, it signaled to donors "they would know the [Clinton] imprimatur had been received." Cecil, who gave himself the titles of chief strategist and cochair, brought in a new executive director, Anne Caprara, who'd worked with him at the DSCC, and a new finance director to replace Justin Brennan, an Obama 2012 alum aligned with Wicks (he'd left to work on a Senate race in Ohio).

By the end of May, Buffy Wicks was out as chief of Priorities and Guy Cecil (above) was in. (Bill Clark/Roll Call)

Cecil also coaxed David Brock into rejoining the board. What's more, according to three sources familiar with the negotiations, Priorities and Brock are in talks about forming a joint fundraising agreement in which Priorities and Brock's presidential-minded groups—including the research-focused super PAC American Bridge 21st Century and the pro-Clinton fact-checking operation Correct the Record—will fundraise together and divide the proceeds. Representatives for Priorities and Brock confirmed the negotiations, but said they were in the early stages and declined to offer any details.

Messina, for his part, remains a cochair and, according to a Priorities official, will raise money for the group. But people close to him say that he is now largely out of the picture. (Priorities, which expects to have a staff of 13 by the end of the summer, moved out of Messina's office in July.)

Cecil told me he'd keep in place almost all of Wicks's transparency measures. But while Wicks and Brennan were full-time Priorities staffers, Cecil and his deputy director in charge of finance, Kim Kauffman, are consultants. (Cecil says he has only one other client at the moment, a small nonprofit, but did not rule out taking on other clients in the future.) In fact, most of the top operatives at Priorities, including Cecil, Priorities President Harold Ickes, and senior advisers Jonathan Mantz and Diana Rogalle, continue to represent other clients, whether as fundraisers, lobbyists, or advisers. This isn't out of the ordinary in Washington, but it can present complications. For instance, Mantz is a lobbyist for BGR Group, a firm cofounded by former Republican National Committee Chairman Haley Barbour. In 2010, Mantz registered to lobby the House, Senate, and multiple federal agencies on behalf of InnoVida, a building-materials start-up that went bankrupt after two executives misappropriated $40 million of investors' money and misled those investors about the company's activities, according to a federal indictment. A judge sentenced both executives to jail time as a result. One of InnoVida's board members was Jeb Bush. Yet should Priorities single out Bush's work for InnoVida, an obvious reply would be to highlight Mantz's lobbying. "When you have other clients, there are always questions about where do your loyalties lie," says a source close to the Clintons. (Mantz declined to comment.)

On July 2, Cecil previewed Priorities' first fundraising report of 2015. (The official filing won't be public until the end of the month, a spokesman told me.) He announced in an email to supporters that Priorities raised $15.6 million from January to June—a number similar to the one reported by the Journal in May before Cecil came aboard. He told reporters that the super PAC had received donations from Hollywood producers Steven Spielberg and Jeffrey Katzenberg and longtime Clinton donor Haim Saban, among others. Cecil also bragged that $12.5 million of the group's total was raised in the previous four weeks—that is, since he'd taken over. "We have a lot of work to do in the months ahead," he said in his announcement, "but we are starting to see some real momentum."

The implication, of course, was that Priorities was a mess until Cecil took over, and then under his stewardship the money came rushing in. I asked Cecil for more details about the fundraising announcement. He told me that the $12.5 million in question was brought in, from solicitation to the end, by him and his team (some of whom, like Mantz and Rogalle, had carried over from the previous regime). However, in the course of my reporting, four sources with direct knowledge of Priorities' fundraising contested Cecil's $12.5 million figure. At most, these sources argued, Cecil could lay claim to roughly $5 million in the first month he was in charge. The remaining funds, they say, were a mix of donations solicited and raised during Wicks's tenure as well as money sent in by unsolicited donors. When I followed up with Cecil about what these sources asserted, a spokesman only reiterated Cecil's $12.5-million-in-four-weeks figure, adding, "We are moving forward with real momentum."

"You have to get her in the room with donors," says a source close to the Clintons.

THE CLINTON DONOR universe is a vast one, but it is largely unaccustomed to being asked to give $10 million or $20 million for electoral politics. After all, the last time a Clinton ran for office, super PACs didn't exist. (There is only some overlap between Obama's and Clinton's big-money donors.) In 2008, Clinton could attend as many campaign fundraisers as possible, ask donors for the then-legal-maximum of $2,300, and rest assured that she'd done all she could. Today, super PACs are appendages of the campaigns. The two can coordinate their fundraising, personnel, scheduling, travel—everything but spending and strategy. That means Priorities can schedule events on the same days and in the same cities as Clinton campaign fundraisers. Clinton herself can attend those super PAC events, pitch donors on supporting Priorities (without mentioning dollar amounts), and then after she exits the room, a Priorities staffer can make the hard ask.

Clinton, despite nominally embracing Priorities as her main super PAC, has appeared at only one Priorities fundraiser. It was held in early May, on the heels of a campaign fundraiser at the billionaire environmentalist Tom Steyer's home in San Francisco. Three people attended the super PAC fundraiser, which was held near Steyer's home: philanthropist Herb Sandler, businessman Steve Silberstein, and philanthropist Laure Woods, all of whom later gave six- and seven-figure sums to Priorities. Jeb Bush, by contrast, has headlined dozens of super PAC events this year.

If there's anything the many factions involved in Priorities agree on, it's that Hillary Clinton—and preferably Bill, too—need to take a more hands-on role if Priorities is to compete with the Republican side. "At the end of the day," a source close to the Clintons says, "you have to get her in the room with donors." There are, to be sure, some limits to what she can do now that she's officially in the race. But fundraisers and Democratic operatives expect her to headline more super PAC events and do what she can within the letter of the law to help Priorities reach its goal of $250 million to $300 million. "I feel pretty confident that we'll have the level of participation that is both legal and necessary to be successful," a senior Priorities official told me.

That Clinton has made campaign finance reform central to her presidential bid, calling for a constitutional amendment to overturn the Citizens United decision, surely muddles future efforts to boost her super PAC. But when I asked about Clinton's stance, Cecil dismissed the idea that it would prevent Democratic donors from funding Priorities. He told me that the party's big givers were savvy enough to recognize the need for reform while seeing the importance in funding a key piece of Clinton's political apparatus. In fact, Cecil told me that Priorities had already secured $9 million in commitments in the first two weeks of July. He said his interactions with donors had so far gone swimmingly: "At the end of the conversation, I haven't had a person say no yet."

This article is from the archive of our partner National Journal.

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