Closing the book on Obama's boulevard of broken dreams

As President-elect Donald Trump begins his triumphant march through Washington, D.C., Friday morning — a march that will end with an event many liberals are still too gobsmacked to even accept — it is difficult to remember the mood of the country just eight short years ago when Trump's predecessor began the same procession. With Trump loudly promising to undo most or all of President Barack Obama's prominent executive orders, to refill Gitmo, and to sign a bill that will repeal the one significant piece of legislation bearing Obama's name, Obama has to wonder, as he watches the spectacle unfold, how it all went so disastrously wrong.

Obama assumed office with perhaps the most impressive cache of goodwill and political capital of any president since the 60s. He had convincingly defeated his Republican opponent — and more, his party had grabbed control of the House and a filibuster-proof majority in the Senate. Obama entered office with the raw power at his disposal to do almost literally anything he wanted, from a legislative perspective.

But Obama had more than just the raw power. He also had the backing of a significant part of the country that was just plain tired of the Republican Party. They were tired of the war in Iraq, which seemed to drag endlessly on with no hope of final resolution. They were tired of the financial crisis and Bush's handling of it, including the TARP plan, which was broadly opposed by Bush's own party. They were tired of Bush himself, who seemed like a decent man but who could never seem to get the right words out of his mouth whenever he was on camera and thus never gave the American people total confidence that he was as much in command of the situation as he should be.

Along came Obama, carrying with him all the promise of being the exact opposite of Bush. In the place of Bush's stammering neologisms, Obama brought soaring rhetoric. In the place of the bitter partisan fighting that permeated Bush's second term, Obama promised a new kind of politics, one built on positivity and change. In the place of Bush's refusal to offer a clear vision of when the war in Iraq would end, Obama promised an unequivocal end to our misadventure in the Middle East. Obama had fierce detractors from the beginning, but the country as a whole was ready for Obama to lead. Obama's approval rating on his Inauguration Day was, according to most polls, near a staggering 70 percent, including 40 percent of Republicans. In other words, Obama was more popular among registered Republicans on his first day in office than Trump currently is with the country as a whole.

It's almost difficult to even remember the many plans Democrats had to reshape the country — and, indeed, the electorate — in the virtually unprecedented two-year window they believed they enjoyed between 2009 and 2011, because so many of those plans utterly failed to come to fruition. Remember card check, which was supposed to vastly increase union membership and financial power? Remember the comprehensive immigration reform they were going to pass that was supposed to provide them with an insurmountable demographic advantage over the Republicans? Remember how Gitmo was going to be closed and our troops were going to be pulled out of Iraq by 2010?

Ultimately, none of these things came to pass for three reasons. The first is that Obama failed to lead his own party in Congress in the critical early days of his term. The second is that he overestimated the amount of time that he would enjoy a filibuster-proof majority, due to the death of Sen. Edward Kennedy (D-Mass.) in August 2009 and the stunning special election to replace him, which saw Republican Scott Brown bring a grinding halt to Obama's unchecked power. Third, he drastically underestimated his need to work with Republicans in the early days of his term.

Democratic strategists have long lamented Obama's choice of priorities in the early days of 2009 and the decision to largely leave the shape of his signature health care bill up to Congressional Democrats. Obama's first bill — the stimulus package — was probably a political necessity for a president who desperately needed to be perceived as doing something to help the growing jobs crisis in America. However, in the course of that fight, he made what would turn out to be a critical mistake by dismissing Republican concerns about the size and scope of the bill with a contemptuous "I won," which hardened Republicans' resolve to never work with Obama again on anything. Republicans took away from that fateful meeting a firm conviction that one day they would be in a position to require Obama to seek their approval, and they privately vowed to withhold it.

The second major legislative priority would turn out to be a strategic mistake. Rather than force through card check or immigration reform — either of which would have improved the Democrats' chances in the looming 2010 elections and beyond — Obama made the choice to push for health care reform first instead. The polarizing fight was enough to evaporate what remained of Republican goodwill for Obama and did much to turn independent voters against his agenda, as well. Worse, Obama failed to actually tell Democrats in Congress what shape he wanted the law to take, which led to months of intra-party bickering about the details of the law, mostly centered around whether the bill would include a "public option" favored by liberals. The party's more progressive members insisted the law was almost worthless without it, and saw the "public option" as first step towards a single-payer system they all favored. However, moderate Democrats like Sen. Ben Nelson of Nebraska wavered on it, concerned about the effect it might have on their re-election prospects in 2010. Liberals begged Obama to forcefully push for the public option within his own caucus, but the president instead kept himself aloof, preferring to state that this was a decision best left to Congress.

By the time the dust settled from the debate, Democrats had accepted a version of the bill without a public option, Ted Kennedy had died, and their access to untrammeled power was over. Unless they did away with the filibuster altogether, Democrats would never again during Obama's presidency have an opportunity to pass a single bill without Republican support. And thanks to Obama's casual dismissal of Republican leadership during the stimulus fight, that support would not be forthcoming.

The goodwill Obama spent on this bitter fight, which concluded without a single Republican vote in support of his legislation, would have dire consequences for every decision Obama would make during the rest of his term. Republicans turned dissatisfaction with both Obamacare itself and the manner in which it was passed into a disastrous election for Democrats in 2010. After taking back the House, Democratic Senate Majority Leader Harry Reid (Nev.) no longer even had a strategic reason to consider nuking the filibuster on legislation, since the House could simply kill any bill the Senate might force through anyway. Republicans were also able to continually fluster Obama's efforts to empty out and close Gitmo.

But if Obama's aloof, detached leadership style served him poorly in fights with Congress, it was disastrous in foreign affairs. Loathe to face open criticism from his generals for an unduly precipitous withdrawal from Iraq, Obama resorted to simply declaring that he had fulfilled his promise to end the war in Iraq in 2010 without actually doing it. Troops remained but were hamstrung by absurd rules of engagement that served to make the morass in Iraq worse. As Iraq became an "out of sight, out of mind" problem for Obama, a new, more virulent strain of Islamic extremism grew in the Middle East.

The growth of ISIS, and the conditions that allowed it to occur, were symptomatic of Obama's entire presidency after the Democrats' shellacking in 2010. Over and over again, Obama grew listless and apparently despondent by his ability to accomplish literally anything on Capitol Hill. He reacted sporadically and fitfully by attempting repeated unilateral actions that were often struck down by the courts. His administration was overruled unanimously by the Supreme Court — including his own nominees — more than any other president in modern history, a symbol of the frustrated petulance that became his default mode action. He frequently displayed disinterest or contempt for real problems as they accumulated on the horizon, including ascendant Russian aggression and an unfolding human rights crisis in Syria that was almost certainly a spillover from his fecklessness in Iraq. He assumed, from the beginning of his presidency, that he would be able to heal race relations in this country simply by the force of his personality, but instead they steadily worsened.

He even seemed to sleepwalk through much of his re-election campaign, taking one of the worst beatings a sitting president has ever taken in a televised debate from the normally mild-mannered Mitt Romney. Even when he regained his footing in the second debate, he displayed contempt for the suggestion that America faced serious problems — including Russia — either at home or abroad. Even though he staggered to a narrow win against Romney in that election, the decisive shellacking Democrats faced in 2014 signaled to Obama that his ability to fundamentally change America in the way he wanted was well and truly over.

As Obama exits stage left in favor of Trump today, he does so as a relatively popular outgoing president, on a personal level. However, even Obama — whose arrogance is at least equal to Trump's, even if he hides it better — cannot help but notice that as he leaves office, America rejected his hand-picked successor in favor of a man who is every bit as much his polar opposite as he was to Bush. He also cannot help but notice that his party has been decimated at both the national and statewide level. He regularly mistook his own (relative) personal popularity for the belief that the country was with him ideologically, when in fact it was not. And although it might have come to be with him ideologically, he was unable — and frankly unwilling — to put in the hard work to change Americans' minds on too many of his policy ideals.

And so he leaves office with troops still in Iraq and Afghanistan, still being shot at by terrorists. Gitmo is still open. Comprehensive immigration reform has not been passed and his executive orders will likely be wiped away soon. Instead of fundamentally changing the electorate towards his party, he has alienated the breadbasket of the country to such a thorough degree that Democrats can now win popular elections by more than 2 percentage points and still lose the Electoral College in a landslide. And his one signature piece of legislation faces imminent dismantling.

Six months from now, all Obama might have to look back on is what might have been.