In March 2009 the Campaign for America’s Future, a top progressive group in Washington, launched a campaign called “Dog The (Blue) Dogs” to pressure conservative Blue Dog Democrats to support President Obama’s budget. When he heard about the effort, White House deputy chief of staff Jim Messina, who was regarded as the Obama administration’s designated “fixer,” called CAF’s leaders into the White House for a dressing down, according to a CAF official. If the group wanted to join the Common Purpose Project, an exclusive weekly strategy meeting between progressive groups and administration officials, CAF had to drop the campaign. We know how to handle the Blue Dogs better than you do, Messina said. Not wanting to sour its relationship with the White House at this early date, CAF complied, and the campaign quickly disappeared from its website. Despite Messina’s assurance, however, the Blue Dogs would remain a major obstacle to the realization of the president’s legislative agenda.

The hardball tactics used by Messina against CAF exemplified how the Obama administration would operate going forward—insistent on demanding total control, hostile to any public pressure from progressives on dissident Democrats or administration allies, committed to working the system inside Washington rather than changing it. As deputy chief of staff, Messina held the same position once occupied by Karl Rove (and Josh Lyman on The West Wing). He worked as a top lieutenant for Rahm Emanuel and became the administration’s lead enforcer after Emanuel left for Chicago. White House communications director Dan Pfeiffer calls Messina “the most powerful person in Washington that you haven’t heard of.” Messina’s dream job was to become chief of staff. Instead, he recently got an arguably more important assignment—manager of Obama’s re-election campaign.

Messina, a longtime aide to Montana Senator Max Baucus, entered Obamaworld in June 2008 as the campaign’s chief of staff. He had impressed Democrats by leading the effort in the Senate to oppose the Bush administration’s push to privatize Social Security and quickly won the trust of campaign manager David Plouffe, who put Messina in charge of day-to-day operations. “I spend the money, so everything’s gotta go through me to get spent, which is the best job ever,” Messina told The New Yorker. “It’s like getting the keys to a fucking Ferrari.” (Messina has been spotted driving a black Porsche convertible in Washington.)

Unlike Plouffe, who became a revered figure among Obama supporters, Messina begins the re-election campaign with a significant amount of baggage. As a former chief of staff to Baucus and deputy to Emanuel, Messina has clashed with progressive activists and grassroots Obama supporters both inside and outside Washington over political strategy and on issues like healthcare reform and gay rights, alienating parts of the very constituencies that worked so hard for Obama in 2008 and that the campaign needs to reinspire and activate in 2012. Obama’s fixer has arguably created as many problems as he’s solved. “He is not of the Obama movement,” says one top Democratic strategist in Washington. “There is not a bone in his body that speaks to or comprehends the idea of a movement and that grassroots energy. To me, that’s bothersome.”

Messina’s allies say he’s a savvy, experienced operative who played a key role in the passage of Obama’s legislative agenda, and is well prepared to lead a tough campaign for the president. “Jim was tasked with bringing together various parts of the progressive community to unite behind the president’s historic agenda—affordable, accessible healthcare for all Americans, repealing ‘don’t ask, don’t tell’ and ending the war in Iraq, among other priorities,” says Hari Sevugan, a Democratic Party spokesman. “Despite their differences, he rallied that coalition behind the president’s agenda and played a critical role in making these common goals a reality. It’s exactly this ability to get things done, along with his deep relationships with grassroots leaders, activists and members of Congress, which will make Jim a strong leader for the president’s re-election effort.” But other Democrats interviewed for this article, who have dealt with Messina in the past, questioned whether he’s the right man for the job, and what his elevation says about the kind of re-election campaign Obama plans to run. (Some declined to speak on the record for fear of retribution.)

Under Messina, Obama ‘12 could more closely resemble the electoral strategy of Baucus or Bill and Hillary Clinton—cautious, controlling, top-down in structure and devoted to small-bore issues that blur differences between the parties—than Obama ‘08, a grassroots effort on a scale modern politics had never seen. “It was a major harbinger to me, when Obama hired him, that we were not going to get ‘change we can believe in,’” says Ken Toole, a former Democratic state senator and public service commissioner in Montana. “Messina has a lot of talents, but he’s extremely conservative in his views on how to do politics. He’s got a tried-and-true triangulation methodology, and that’s never gonna change.” The Democratic National Committee declined to make Messina available for an interview.

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At the beginning of the healthcare debate in 2009, many Democrats were justifiably concerned about the role that Baucus, chair of the powerful Finance Committee, would play in shepherding the Obama administration’s domestic policy priority through the Senate. Baucus had brokered the passage of George W. Bush’s 2001 tax cuts and 2003 Medicare prescription drug plan, and had spent the better part of the Bush presidency cutting deals with Republicans and infuriating fellow Democrats. Other transgressions included voting for the war in Iraq, the energy bill, the bankruptcy bill and to confirm Supreme Court Justice John Roberts. Among Senate Democrats, only Nebraska’s Ben Nelson had a more conservative voting record on economic issues than Baucus. Moreover, Baucus accepted the most special-interest money of any senator between 1999 and 2005, and had at least two dozen staffers working as lobbyists on K Street, including for healthcare companies adamantly opposed to reform.

Despite these obvious warning signs, Messina emerged as the leading advocate for his old boss during the healthcare debate and the top administration conduit to his office. “He is perfectly positioned to do this,” Messina told the New York Times in June 2009. Messina told the Washington Post he regarded Baucus as a father figure. “Messina will freely tell you that everything he knows, he learned from Baucus,” says Eric Feaver, president of the Montana teachers union.

The administration gave Baucus and his handpicked “gang of six” senators nearly unlimited time to secretly craft a bill, which proved to be one of its most glaring strategic missteps during the healthcare debate. “Some of the difficulty that healthcare is in today is Max’s fault,” says former Montana Democratic Congressman Pat Williams. “He took too long, he tried to satisfy too many—including people that were going to vote against it from the onset—and he gave the opposition time to regroup. That was a bad political decision on his part, and many people out here believe, rightly or wrongly, that Messina was part of that foot-dragging and vacillation.”

The administration deputized Messina as the top liaison to the Common Purpose Project. The coveted invite-only, off-the-record Tuesday meetings at the Capitol Hilton became the premier forum where the administration briefed leading progressive groups, including organizations like the AFL-CIO, MoveOn, Planned Parenthood and the Center for American Progress, on its legislative and political strategy. Theoretically, the meetings were supposed to provide a candid back-and-forth between outside groups and administration officials, but Messina tightly controlled the discussions and dictated the terms of debate (Jane Hamsher of Firedoglake memorably dubbed this the “veal pen”). “Common Purpose didn’t make a move without talking to Jim,” says one progressive strategist. During the healthcare fight, Messina used his influence to try to stifle any criticism of Baucus or lobbying by progressive groups that was out of sync with the administration’s agenda, according to Common Purpose participants. “Messina wouldn’t tolerate us trying to lobby to improve the bill,” says Richard Kirsch, former national campaign manager for Health Care for America Now (HCAN), the major coalition of progressive groups backing reform. Kirsch recalled being told by a White House insider that when asked what the administration’s “inside/outside strategy” was for passing healthcare reform, Messina replied, “There is no outside strategy.”

The inside strategy pursued by Messina, relying on industry lobbyists and senior legislators to advance the bill, was directly counter to the promise of the 2008 Obama campaign, which talked endlessly about mobilizing grassroots support to bring fundamental change to Washington. But that wasn’t Messina’s style—instead, he spearheaded the administration’s deals with doctors, hospitals and drug companies, particularly the Pharmaceutical Research and Manufacturers of America (PhRMA), one of the most egregious aspects of the bill. “They cared more about their relationship with the healthcare industry than anyone else,” says one former HCAN staffer. “It was shocking to see. To me, that was the scariest part of it, because this White House had ridden in on a white horse and said, ‘We’re not going to do this anymore.’” When they were negotiating special deals with industry, Messina and Baucus chief of staff Jon Selib were also pushing major healthcare companies and trade associations to pour millions of dollars into TV ads defending the bill. (Messina did have allies in the progressive community. Jon Youngdahl, chief of staff at the SEIU, praised him for the “ability to pull together progressives with diverse points of view” on healthcare, while Democratic strategist Robert Creamer noted that “Messina’s mission was to get something passed.”)

Messina was adamant about shielding Baucus from any public pressure, whether it be concerns over the absence of a public option in the Finance Committee bill or his fruitless negotiations with GOP senators, Kirsch says. “The aggressive suppression of outside pressure was done by Messina,” he adds. “I can’t imagine that the president knew about it.” Messina and his allies tried to stop HCAN from sending a letter to senators expressing displeasure with Baucus’s bill and also tried to prevent the group from running a TV ad praising the House version of the bill. HCAN’s organizer in Montana, Molly Moody, was banned from Baucus’s office and prevented from attending his public events. (Baucus’s office did not reply to a request for comment.) “This is something Messina did in Montana—any group that did any outside pressure on Baucus was iced out,” says Kirsch. “He did the same thing with HCAN in the White House.” When he worked for Baucus, Messina even kept a list of his political enemies on an Excel spreadsheet. “Ultra-paranoid behavior is very much a hallmark of Messina,” says Ken Toole.

The administration’s aversion to popular mobilization on behalf of healthcare reform, either by progressive groups or the Obama-aligned Organizing for America (OFA), backfired spectacularly when Tea Party activists organized against the bill in the summer of 2009, catching Democrats off guard. Ever since then, the White House, despite the bill’s eventual passage, has largely been playing defense on healthcare. Says one Democratic operative of Messina: “I hope he’s better at political campaigns than at managing big, important pieces of legislation.”

Gay rights was another major issue on which Messina clashed with Obama supporters. The relationship between the administration and gay rights groups was strained from the outset, when Obama chose Rick Warren to deliver his inaugural invocation. “It is difficult to comprehend how our president-elect, who has been so spot-on in nearly every political move and gesture, could fail to grasp the symbolism of inviting an anti-gay theologian to deliver his inaugural invocation,” wrote Joe Solmonese, president of the Human Rights Campaign (HRC), in the Washington Post.

After reading the op-ed, Messina sternly rebuked Solmonese during a meeting at the White House. “I’m never going back to another meeting like that again,” Solmonese angrily told his staff afterward. From then on, HRC, to the consternation of other gay rights groups, toed the administration line.

With Messina as a top liaison to the gay rights community, the White House was reluctant to make repealing “don’t ask, don’t tell” (DADT) a key legislative priority. “The White House, under Rahm and Messina, suffered from political homophobia,” says Joe Sudbay, who writes about gay rights issues for AMERICAblog. “They’re not homophobes in the traditional sense of the word, but they think it’s dangerous to do gay issues in politics.” Groups that questioned Messina’s strategy, such as the Servicemembers Legal Defense Network, were frozen out of key White House meetings. “I felt like he was constantly angry with those of us who would not fall in line,” says Alex Nicholson, executive director of Servicemembers United (no relation to SLDN).

The president reiterated his commitment to repealing DADT in his second State of the Union address, in January 2010. But a few days later, in a meeting with gay rights groups, Messina spoke of the difficulty of ending DADT in the midst of two wars, a remark many of the activists in the room found offensive. The Pentagon needed time to survey the troops on the impact of repeal, Messina said, which wouldn’t be done until December. That meant there likely wouldn’t be a vote on repealing DADT until 2011, even though the Democratic Congress of 2009-10 presented the best opportunity to repeal the law. “People on the Hill kept saying, ‘The White House doesn’t have a strategy’ right up through the lame duck session,” Sudbay says.

On November 16 gay rights activists picketed the Common Purpose meeting and shouted at Messina as he entered, “What’s your plan?” It was only after the administration’s tax cut deal with Congressional Republicans enraged liberal Democrats that repealing DADT became a last-minute priority for the White House, which badly needed a legislative victory to soothe its progressive base. “It was a Hail Mary pass with ten seconds to go in the fourth quarter,” says Brad Luna, a leading gay rights activist who runs a progressive-oriented PR firm. Sudbay says the DADT repeal passed “in spite of Messina,” and Luna agrees. “At the end of the day I’d definitely label him an impediment,” Luna says. “He was not falling on a sword to get DADT passed.”

Solmonese offered a different perspective, calling Messina “unquestionably one of the great unsung heroes of DADT repeal.” The two stood side by side on the Senate floor as the bill cleared the body on December 18. When the sixtieth vote came in, Solmonese said, Messina began to cry. After it was all over, Messina touted repeal as a major victory for the administration and an example of Obama’s commitment to his base.

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Messina grew up in Boise, Idaho, became active in politics at the University of Montana and cut his teeth as an organizer for Montana People’s Action, helping disenfranchised trailer park residents in Missoula. Like Obama, he refers to himself as a community organizer at heart. When Messina started working for Democrats in the Montana legislature, “he was a flaming liberal,” remembers Gene Fenderson, a veteran state labor organizer. But when he took a job with Baucus in 1995, Messina shed his liberal roots. “He changed philosophies in a nanosecond,” Fenderson says. Messina became fiercely loyal to Baucus and wasn’t shy about doing his boss’s dirty work. “Jim is one of those campaign workers who reflects his boss,” says Pat Williams. “Max does not easily suffer dissent, and Jim saw himself as Max’s enforcer.”

In 1999 Messina became chief of staff to New York Congresswoman Carolyn McCarthy but returned to manage Baucus’s re-election campaign in 2002. The campaign became infamous when the Montana Democratic Party ran an ad showing his GOP opponent, Mike Taylor, a former hairdresser, fondling the hair and face of a male client while wearing a ’70s-style leisure suit. Taylor dropped out days after the ad aired, accusing the Baucus campaign of “character assassination and personal destruction.” Gay rights groups condemned the ad as antigay, but it greatly enhanced Messina’s reputation as a top Democratic operative. “He touted the ad as the way to do politics in the West,” said Toole.

Baucus easily won re-election that year. Not long after, Messina visited Montana Democratic Party chair Bob Ream and demanded that he fire his executive director, Brad Martin. The Baucus camp regarded the state party as too grassroots and insufficiently loyal to Baucus. Ream resisted and his executive board unanimously recommended that Martin be retained. Then Baucus insisted that Ream resign. He refused. When Ream ran for re-election in 2004, Messina tried to find somebody to run against him, but could not.

These kinds of interventions earned Messina a mixed record back home. Baucus’s crew, colloquially known as the Montana mafia, loved him, but other Democrats did not. Those who know Messina say that, his politics aside, he can be funny, charming and generous, but also temperamental, vindictive and controlling. “People either like Jim or they don’t,” says Pat Williams. “I know a number of people who do not like him, which is unusual for political apparatchiks. The people who don’t like Jim seriously don’t like him. I have found none of those faults with Jim personally, but the truth is, they’re out there.” To this day, however, many of his critics shy away from publicly criticizing him. “If you want to have a future in Montana politics, you don’t criticize Jim Messina,” says James Anacker, a former field rep for Baucus. “That would be career suicide. People are afraid of him, to tell you the truth.”

Messina has become a controversial fixer for Obama as well. He generated bad press for the administration by offering a job to Colorado Democratic Senate primary candidate Andrew Romanoff when the administration was trying to get him not to run against incumbent Michael Bennet in 2010. Messina also reportedly praised the administration’s firing of Agriculture Department official Shirley Sherrod after a tape surfaced of her allegedly discriminating against a white farmer, even though Secretary Tom Vilsack had dismissed her before learning that right-wing blogger Andrew Breitbart had doctored the footage. “We could have waited all day—we could have had a media circus—but we took decisive action, and it’s a good example of how to respond in this atmosphere,” Politico reported, quoting a source who paraphrased Messina’s remarks. That “decisive action,” however, unfairly cost Sherrod her job. The administration later apologized and offered her the post back. It was one of a string of embarrassments for Obama’s political team.

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Messina has spent his early days as campaign manager meeting with wealthy Obama megadonors on a “listening tour.” He has assiduously cultivated these relationships in his career, previously serving as Baucus’s top liaison to Wall Street and organizing lavish fundraising junkets in Montana. Baucus kicked off his 2008 re-election campaign by bluntly asking fifty lobbyists to raise $100,000 each. The Obama campaign hopes Messina’s connections will come in handy as it tries to amass a $1 billion war chest for 2012; Messina has already asked Obama’s finance committee to raise $350 million by the end of this year. But early indicators signal that Messina’s task won’t be so easy this time around. Corporate America no longer regards Obama as an ally, while many donors from 2008 are disillusioned with the administration’s legislative compromises and political timidity.

After the 2010 election, Messina spoke at the winter meeting of the Democracy Alliance, a group of wealthy progressive funders. He gave two PowerPoint presentations, including one on the administration’s accomplishments—the stimulus, the Lilly Ledbetter Fair Pay Act, healthcare and financial reform. The other was on what was still to come—immigration reform, the START treaty, repealing DADT. “Jim, you’re missing a word,” one donor told him during the Q&A.

“What word?” Messina responded.

“The word ‘jobs,’” the donor said.

“Messina got a lot of tough questions from people who used to love him,” says one person who was in the audience. “It was like a room of scorned lovers.”

Even as Messina jet-sets around the country, huddling with big donors, will the campaign cultivate the small donors and grassroots activists who powered and shaped the ‘08 Obama campaign? On February 1 Politico’s Mike Allen reported that “Obama’s political operation is quietly using the afterglow of his State of the Union address to begin activating grassroots supporters as the start of a continuous wave of engagement that will culminate when he stands for reelection on Nov. 6, 2012.” As part of the effort, OFA offered T-shirts to activists featuring a tag line from Obama’s speech: “We do big things.” The article provided a revealing glimpse into the campaign’s early strategy for 2012—woo wealthy donors and sell T-shirts to the masses.

The re-election campaign, at least at this stage, resembles an Obama administration reunion. Messina’s deputies will be Jennifer O’Malley Dillon, the DNC’s former executive director, and Julianna Smoot, the ex–White House social secretary. Mitch Stewart and Jeremy Bird, the heads of OFA, will oversee field operations. The new-media team, such a big part of the ‘08 campaign’s success, has yet to come together. So far the campaign seems content to rely on old hands rather than bring in new blood, which some Democrats see as a mistake. “There’s been some grumbling that, frankly, given how inept the White House was politically in the first half of the Obama presidency, why on earth would you want to move those people over to the campaign?” says a former top Obama campaign official.

In certain ways, it’s easier to start a campaign as a blank slate. In 2007 Plouffe was not a particularly unconventional thinker, but because he was facing the Clintons, the Obama campaign wisely decided to experiment with innovation and cede some control to grassroots supporters, integrating bottom-up politics into the strategy of the campaign’s upper brass. Obama’s advisers knew that if they simply ran a second-rate version of the Clinton campaign, they would lose. But now that Obama is the establishment candidate, it’s unlikely he’ll follow the same playbook that worked so well in ‘08—or will even be able to. Regardless, that’s not how Messina operates. “Clearly they want to recapture the magic, which is going to be very hard for them,” says Roger Hickey of the Campaign for America’s Future. “It’s hard to get excited about a guy who’s constantly compromising, especially if unemployment stays above 8 percent.” One could say the same thing about Messina.