Our challenges may be new. The instruments with which we meet them may be new. But those values upon which our success depends - honesty and hard work, courage and fair play, tolerance and curiosity, loyalty and patriotism - these things are old. These things are true. They have been the quiet force of progress throughout our history. What is demanded then is a return to these truths. What is required of us now is a new era of responsibility - a recognition, on the part of every American, that we have duties to ourselves, our nation, and the world, duties that we do not grudgingly accept but rather seize gladly, firm in the knowledge that there is nothing so satisfying to the spirit, so defining of our character, than giving our all to a difficult task.
This is the price and the promise of citizenship.
This is the source of our confidence - the knowledge that God calls on us to shape an uncertain destiny.
--President Obama, Inaugural Address, 20 Janaury 2009.
President Obama succeeded in two out of three key, instrumental aims of any American President: to win power and to get re-elected. He failed at the non-trivial third aim: to pass on or leave power to a candidate friendly to his policies. (There should be a Machiavelli quote to support the general thought avant la lettre, but I can't remember it.) The proximate cause of this failure is due to his strange willingness to emulate his predecessor, President Bush (43), and run and stick with a Vice-President who, regardless of his other merits, could not for all intents and purposes succeed him. This strategic failure is surprising because President Obama has been interpreted as especially strong on thinking through the long game (see, for example, Andrew Sullivan). While the first law of politics is that nothing lasts, it is also true that some stuff can last longer than others. For, whatever President Obama hoped to achieve in the medium-to-long-run requires institutions, norms, and people to protect and develop his legacy.
My suspicion is that President Obama failed to recognize the challenge, when he was still in the position to do something about it, because of his own commitment to a progressive understanding of history. This commitment is expressed in his 2012 political slogan (forward), his defense of Hillary Clinton ("progress is on the ballot"),* and, especially, in his inaugural address (quoted above). For, while Obama explicitly recognizes that our collective "destiny" is "uncertain," he is committed to the idea that truthful values and duties, which he claims are "the quiet force of progress," have as an expected by-product success.
His mistake here is that these values (honesty, hard work, courage, fair play, tolerance, curiosity, loyalty, and patriotism) only reliably and regularly produce success worth having in the context of reasonably well-functioning institutions, including the institution of justice. In other contexts these may well be foolish or promote, say, fanatical ends.** But if you think that such success is a to-be-expected reward and reliable by-product of the energetic and dutiful exercise of these 'truthful' values, you are likely to fail to recognize that their outcome may also be dependent on, let's say, more hidden forces, less noble values, or even luck.
Perhaps, the previous paragraph is wrong. Perhaps, Obama's failure was just a matter of inexperience. But what is manifest is that the moment Hillary Clinton was nominated it was clear the final destiny of his Presidency was out of his hands. (That's, of course, compatible with the thought that a victory by her would have been better for the survival of his projects.) For all their shared policy-ends, she represents different would-be symbolic achievements and, more importantly, a return to Wall Street's preeminence in politics that voters had rejected in his initial victory. And this gets me to his second failure: Obama understood himself, I think, as the person who could provide "a watchful eye" to Wall Street, and ensure "the market" would not "spin out of control;" that he could protect citizens from Wall Street and ensure that Wall Street would continue to flourish. For all I know this is a winning economic formula and generates both jobs and donations from Wall Street; but it's not a winning political formula among a population that is asked to sacrifice while the bankers are bailed out and left to keep their bonuses.
The final failure is Obama's disastrous foreign policy. In his efforts not to repeat the blunders of his predecessor, who had a fondness for grotesque wars of choice, Obama ended up potentially fatally undermining Pax Americana, squandering the Arab Spring (and facilitating a return to dictatorship in Egypt) and being witness to murderous campaigns by our nominal allies (e.g., Saudi Arabia in Yemen) as well as fuelling a brutal civil war (Syria) for no political gain and at great human cost. Meanwhile, NATO is close to imploding and a would-be-ally, Ukraine, was dismembered. After eight years, Obama is party to the remarkable fact that Putin's Russia -- an aging country with an economy the size of the Netherlands, but willing to step into the vacuum Obama permitted -- is seen as a great power able to shape the destiny of the world.
While it is true that military "power alone cannot protect us," and that "security" can emanate "from the justness of our cause," as Obama said in his first Inaugural, he was profoundly mistaken to think that a stance informed by "humility and restraint" would secure America's interest in the world and, thereby, its protection of those in need in its hard-won empire. From the previous sentences it does not follow that America and the world needs selfish, brash and unrestrained arrogant leadership. But that's the theme of a different presidency.