The most important red line of Barack Obama’s presidency was scrawled hastily in January 2007, a few weeks before he even announced he was running for president.


Soon-to-be-candidate Obama, then an Illinois senator, was thinking about turning down an invitation to speak at a big health care conference sponsored by the progressive group Families USA, when two aides, Robert Gibbs and Jon Favreau, hit on an idea that would make him appear more prepared and committed than he actually was at the moment.


Why not just announce his intention to pass universal health care by the end of his first term?


Thus was born Obamacare, a check-the-box, news-cycle expedient that would ultimately define a president.


“We needed something to say,” recalled one of the advisers involved in the discussion. “I can’t tell you how little thought was given to that thought other than it sounded good. So they just kind of hatched it on their own. It just happened. It wasn’t like a deep strategic conversation.”


(PHOTOS: 25 unforgettable Obamacare quotes)


It’s not exactly fair to call Obama a reluctant warrior on health care reform — not after all he has staked on the biggest single roll of the legislative dice in a half-century. But it took him years to evolve from a skeptical neophyte playing catchup to Hillary Clinton and John Edwards to a chief executive willing to risk his political capital and legacy and the fate of his own party on the principle of affordable, subsidized, government-mandated national health coverage.


The consequences of that offhand promise are still reverberating. Its greatest test lies just ahead on Oct. 1, opening day for enrollment in Obamacare. A flop would be nothing short of the greatest political and policy cataclysm of his career and a mortal blow to a core Democratic principle that government can still do big things.


The tortured process that led to passage of the Affordable Care Act has been amply documented. Less chronicled is just how Obama gradually fell in love with an ugly-duckling issue, and his slow descent from ambivalent detachment to emotional investment in a cause his aides initially dismissed as “Hillary’s thing.”


Yet even after the law passed, some of Obama’s ambivalence — rooted in his desire to dodge the political backlash — lingered. For Republicans, Obamacare has become a rallying point and fundraising tool, but the West Wing always wanted to pass the thing and move on. That has accounted for a sales job that has been, until this fall’s big implementation push, sporadic at best and dangerously lax in the view of many ACA advocates.


(WATCH: Health care: What Obama said, why it mattered)


Obama’s legacy on health care began with the pressure to say something, anything, at the progressive health conference a year before the first presidential primary votes were cast. He needed to keep up with Clinton, his party’s front-runner, and Edwards, who was trying to carve out space to Clinton’s left as the party’s liberal standard-bearer.


Favreau, who would go on to become the chief White House speechwriter, said they wanted Obama “to say something bold and ambitious about health care.”


“He had previously talked about how every year and every election we keep talking about health care and nothing ever happens,” Favreau said. “So we came up with that promise, really one of the first.”


The candidate jumped at it. He probably wasn’t going to get elected anyway, the team concluded. Why not go big?


“In the 2008 campaign, affordable, universal health care for every single American must not be a question of whether, it must be a question of how,” Obama said at the Families USA conference. “We have the ideas, we have the resources, and we must find the will to pass a plan by the end of the next president’s first term.”


(WATCH: Boehner celebrates House GOP 'victory' over Obamacare)


Even after his pledge, though, it took months for Obama to buy in.


In March 2007, he found himself on the same stage with a highly confident Clinton at another health care forum, this one sponsored by the Service Employees International Union in Las Vegas.


Obama staggered through a discussion that left policy wonks convinced that he was out of his league, particularly when compared to Clinton, arguably the nation’s premier expert on health care after her unsuccessful attempt to enact reform in the 1990s.


While she dominated, he was confronted by an audience member who asked why he didn’t have a health care plan yet. He responded that his campaign was only eight weeks old and promised to come up with one soon. At one point, in response to a question about health care disparities among minorities, Obama talked about lead poisoning as Clinton aides giggled.


Obama knew before he walked off the stage that he had screwed up.


“He conceded that he really got his head handed to him — and that didn’t happen very often,” said former Sen. Tom Daschle (D-S.D.), an early Obama adviser. “It was a real catalytic moment.”


Obama crammed, law-school style, on the details. He became “a student of health policy,” Daschle said, consulting with liberal think tanks like the Center for American Progress, reading the research, learning the language and drawing up a plan.


He was pulled deeper into the issue as he traveled the country and listened to the stories of health care hardships told by voters along the rope line, aides said.


But the moment that cemented Obama to Obamacare came in January 2008, when Sen. Ted Kennedy, the party’s liberal conscience and most revered elder statesman, told the Illinois freshman he would endorse — on the condition that Obama kept his promise to make health care his top domestic priority beyond propping up the collapsing economy.


It was a bit of a bluff, former Kennedy aides tell POLITICO: The aging Massachusetts senator, who would soon be felled by a brain tumor, probably would have backed Obama anyway.


But Obama repeated his pledge and Kennedy, hardheaded to the last, immediately steered two of his policy advisers to the task of planning, so Obama couldn’t back off for lack of a viable legislative strategy. To this day, some of Obama’s current and former aides cite the Kennedy commitment as a key reason why he refused to give up even when most of his inner circle counseled him to do just that.


“He felt an obligation,” Daschle said of Obama.


Still, Obama continued to attack Clinton even as he took up her life’s mission.


At the advice of his political advisers, Obama sought to undercut Clinton by accusing her of pushing for an individual mandate — an idea borrowed from Republicans that polled poorly with independents and conservative Democrats in critical battlegrounds like Pennsylvania and Ohio.


Aides say Obama was simply looking for any way to differentiate himself from an opponent whose basic policy positions were indistinguishable from his own. After Clinton dropped out in June 2008, Obama was privately telling his staff that any health care reform he proposed would most likely include a mandate.



At a July 2008 meeting with senior advisers, pollster Joel Benenson ran through numbers detailing the political vulnerabilities of Obama’s health care plan. Assembled in a conference room at the Chicago campaign headquarters, the advisers concluded that Obama shouldn’t talk about it as much during the general election. Obama dismissed the counsel.


“You know, I plan to do health care, I plan to make my first year about health care,” Obama said, according to a campaign official present. “So you guys need to figure out how to sell it.”


By the time he won the election, less than two months after the start of the worst recession since the Great Depression, it seemed that his first and only priority would be rescuing the economy.


But the large Democratic margins in Congress told a different story.


Armed with a House majority, a Senate supermajority and White House chief of staff Rahm Emanuel’s don’t-let-a-crisis-go-to-waste philosophy, Obama was in the market for a big domestic policy crusade to mobilize and energize Democrats around.


There were three big-ticket items to choose from: climate change, immigration reform and health care.


Emanuel and many other Obama advisers urged him to skip health care, the graveyard of White House ambitions from Harry Truman to Hillary Clinton. Emanuel, who presciently predicted an epic conservative backlash, begged Obama to reconsider — and the president responded with a slap at Emanuel’s old boss Bill Clinton, telling him that he didn’t get elected to “do school uniforms,” according to an account shared with author Jonathan Alter.


Obama also calculated that Democrats would unite behind health care, but not necessarily climate change or immigration reform, which remained divisive within the party.


When the fight turned ugly over the August 2009 recess, just as Emanuel predicted, Obama once again faced pressure from his inner circle to back down. Instead, the president gave what his advisers considered one final shot.


They had begun viewing their health reform fight as an existential moment in his presidency, and stealthily planned a highly unusual prime-time address on health care to a joint session of Congress in September.


The idea was to re-energize shell-shocked Democrats and regain the initiative. To do so, he summoned the man who had been a catalyst for his own conversion on health care two years earlier: Ted Kennedy.


Obama quietly prepared two versions of his speech: a widely circulated draft that ended with an anodyne closing statement — and another, secret copy that included an excerpt of the letter that Kennedy sent Obama shortly before his death in August 2009.


West Wing aides figured the first draft would be leaked, giving the second even greater emotional impact — a showman’s move the late Massachusetts senator would have appreciated.


“[W]hat we face is above all a moral issue; that at stake are not just the details of policy, but fundamental principles of social justice and the character of our country,” wrote Kennedy.


The speech injected just enough life back into the issue. The House passed a bill in early November, and the Senate followed on Christmas Eve morning. The only thing left to do was reconcile the two different bills and send it back through for final passage — no small feat, but within reach.


That is, until Republican Scott Brown was elected to fill Kennedy’s Massachusetts Senate seat, robbing Obama of his crucial 60th Senate vote.


The mood inside the West Wing was morose. Almost everyone viewed Brown’s victory as a death blow.


Obama’s top messaging adviser, David Axelrod, dropped by a meeting of the communications staff to offer a wry suggestion of how Gibbs, now Obama’s press secretary, should answer reporters’ questions about the fate of Obamacare.


“Health care is not dead,” Axelrod offered, according to an official who was present. “It’s just sleeping.”


Obama, along with Democratic congressional leaders, especially Nancy Pelosi, made the fateful decision to forge ahead anyway, infuriating Republicans who thought the White House should’ve taken a hint from the Massachusetts election, the furious voter backlash since August and the dismal poll numbers.


By the time Obamacare was signed into law in March 2010, Obama had committed fully to the fight, surprising even those closest to him by the intensity of his personal commitment, his desire to achieve something historic and — last but not least — his fear of being publicly humiliated by a defeat.


The backlash has been more intense and sustained than the West Wing and congressional Democrats ever expected. An inconsistent and weak counterattack and the White House’s reluctance to spend more capital on the issue left Obama’s signature legislative achievement orphaned in ways that could permanently weaken the law.


But on that morning of March 23, 2010, Obama signed the Affordable Care Act, invoking the image of his late mother in an emotional ceremony that underscored how far he had come from his offhanded leap into the fight three years earlier.


The night the bill passed is the “most satisfied I’ve seen him,” said Obama’s senior adviser Dan Pfeiffer, the highest-ranking member of Obama’s 2008 crew still working in the West Wing. “It was really hard, but it was really important — a historic thing that many presidents tried and many presidents failed. He was incredibly emotionally invested, and he remains to this day.”



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