As deeply as I can look into history, and as much as I can penetrate the logic of human society, my conclusions on this are not the least bit tentative or lacking in confidence: Barack Obama is either the best President we've ever had, or more humbly, equal to the best Presidents we've ever had (and thereby one of their number). A more detailed breakdown of these conclusions follows.
First, I want to make clear that some degree of situational relativism is unavoidable - you cannot judge anything meaningfully in a vacuum. Otherwise you might as well unfavorably compare a Mercedes to a Daewoo because you tested the former by driving it up a volcano and the latter on a suburban street.
We all know how great a Democratic President can be when Congress does whatever it's told (e.g., FDR) and has a highly disciplined, motivated public; and how diabolical a Democratic President can be under the same Congressional climate with a divided public (LBJ); but what about a Democratic President who is literally tested in every way: What about a Congress so hostile they question your very legitimacy as an American on a daily basis, threaten impeachment as many times as there are hours in the day, and obstruct every single appointee and piece of legislation on your agenda as a matter of course even if they had previously supported it? What about managing to endure and thrive in the glare of a deranged, lying media controlled by an oligarchy of your enemies that spreads 24/7 propaganda against your administration and party? What about an opposition that has unlimited, unregulated funding not only from corporations that have accepted trillions of dollars in no-strings-attached public bailouts, but from hostile foreign countries (e.g., China and Saudi Arabia) that have a vested interest in controlling American politics through Republican corruption?
Without meaning to belittle the past, frankly Nazi Germany, Imperial Japan, and the Soviet Union don't seem nearly as insurmountable in comparison - at least from the perspective of the White House. When taken in the context of political hyper-corruption, the transmogrification of the GOP into an ultra-malignant, treasonous crime syndicate, the disfigurement of news media into an engine of lunatic partisan propaganda, and the total domination of petty corporate tyranny over every aspect of our lives, the problems we confront today come to seem like the greatest challenges this nation has ever faced. I'm sure a G.I. storming Omaha Beach would disagree about the relative hardships, but as an overall republic, we at least had each other - we had a rational faith that The Enemy was Over There, not surrounding us and poisoning our children's food and minds while stealing their future. The closest President to have faced comparable conditions to Obama would be Lincoln, and frankly Lincoln had it easier.
The Confederacy, despite its agricultural wealth, was not rich by any stretch of the imagination - it had a very backward industrial capacity, and was at best looked upon positively by international financial interests as a source of simple commodities like cotton and tobacco: Not at all a keystone to any economy beyond its own. In fact, apart from its share of America's enduring frontier appeal as a land of rugged adventure, nobody outside the South liked the South. Despite the genteel trappings of its plantation aristocracy, they were seen rightly as pretentious bumpkins playing at nobility by the real deal in Europe. Nobody liked slavery who wasn't already acculturated to it, and even those who were dismissive of the issue found the Southerner's fanatical devotion to the institution puzzling if not viscerally disturbing. To be perfectly blunt, nobody liked the Confederacy. Nobody.
Plenty of other countries were willing to cynically profit from the Civil War - Lincoln had to warn Britain not to try running the Union naval blockade to acquire cotton shipments from the South - but nobody actually wanted to help the Confederates, and the Confederate view of the outside world was sufficiently solipsistic that they never made any serious attempt to seek it. Their society was more of a blurred window into medieval feudalism than anything resembling American society, let alone the highly educated, meritocratic ideals sweeping European civilization at the time. It basically had nothing going for it but endemic hatred of the black man (after all, "we hate those whom we wrong") and Yankees who were constantly earning their ire by being better-educated and more prosperous without slaves than the South was able to be with them and vast agricultural resources.
That isn't to say the Civil War was a fait accompli for the Union - by no means. The malicious spirit of the army of slavery could very easily have wreaked havoc far North of the Mason-Dixon line if Confederate strategy and logistics had favored it. But the nation's soul was never in danger, despite the division of its population - it had remained exactly where it began, in the Northeast, and spreading Westward. It is far more difficult to say that about America today, given the pervasiveness and universality of the corruption. We do not control our own lives, and people hostile to our nation's core values control all of our mass-media sources of information. Faceless corporations own our homes, own our cars, draw the zoning lines in our cities to benefit themselves, take over roads and public spaces (and police! and jails!), tells us where we can go and when, educates our children in how to be obedient workers and insatiable consumers, and "informs" us of what they want us to know while ignoring anything that does not serve their agenda. Their money now draws from a bottomless international well fed by the slave labor of billions, not mere millions. That is the Uber-Civil War into which Barack Obama became President of the United States.
And yet even without that context, I have little trouble stating the following conclusions - Barack Obama is...
1. The most liberal President ever.
2. The most accountable President ever.
3. President of the most transparent administration ever.
4. The most committed to civil rights and equality ever.
5. The most committed to science and technology ever.
6. Either the most, or tied with the most, competent and intelligent President ever.
7. The hardest-working President ever.
8. The most globally-respected, loved, and feared (by our enemies) President ever.
9. Either the most, or tied with the most, politically courageous President ever.
10. Most, or tied with the most, honorable and honest President ever.
I think back to the Presidents before Obama in my lifetime, and think "Ugh, what a bunch of sludge." Don't get me wrong, Bill Clinton was a benign President who made a lot of good managerial decisions, but he was the "leader" of a time in American history characterized by self-satisfied navel-gazing and increasing selfishness. He reflected and moderated, rather than transcended, the negative impulses of the time, and his biggest contribution was to distract Republicans into quixotic jihads against himself personally so they couldn't spend all their time destroying the country. His presidency was a good one, but ultimately just a speed bump on the road to entropy - his liberalism and progressivism were superficial, and he lacked the gravitas of authority. Everything he did came with an implicit plea for acceptance, a kind of neediness that was never very persuasive even when his arguments were sound. I like Bill Clinton, and I wouldn't hesitate to hire his management under other times of plenty and stability, but he is a not a man I would follow into Hell or even Branson, Missouri.
Then I think about what I know of the modern Democratic Presidents before my time - Carter, Johnson, Kennedy, Truman, and Roosevelt. I don't think much about Wilson, because his administration was right on the cusp of the transition point when values first came into distinct focus, and he had a strange mix of progressive policies mixed with outright authoritarianism that just wouldn't place in today's political scene. But I think about Carter and his deer-in-headlights helplessness in the face of the nation's problems and internal institutional resistance to reforms he sought; his seemingly endemic cluelessness - painfully visible even watching his speeches today - about how things look and what a situation calls for; his slow-paced, countrified, reverential attitude making it clear he thought himself to be President of an America that hadn't existed in decades.
Carter was no fool - he was a trained nuclear engineer - but he had no conception of political context or institutional inertia, and all the policies he instituted by fiat as President were swept away with ease the moment he left office. There was no trace of his administration within a year of Ronald Reagan's inauguration, if not sooner, because Carter left behind no bulwark of statutory legacy for the Norquist wrecking crew to surmount - tearing it all down was as easy as taking down the solar panels Carter had installed on the White House roof. His presidency is the strongest cautionary tale of left-wing fallacies about the power of an administration to affect change without the support of Congress and existing Executive institutions - even his Executive orders, when they were inconvenient or impractical to implement, were simply ignored by his subordinates, and once he was gone there was no need to even pretend to be observing them anymore. Jimmy Carter is a great human being, but he was a terrible leader of men.
Then there was Johnson, who in many ways was the inverse of Carter: Diabolically clever, always with some machination afoot, and gracefully able to wend the devious ways of bureaucracy and Congressional process to get his agenda through. But the man was corrupt at heart, and his social programs were not about making a better country - they were just populist vanity projects, like Caesar handing out free bread and absolving public debts, and the Vietnam War was just another part of that general policy of bribery-as-governance. The fact that he originally put forward such progressive programs is laudable, but the fact that he ultimately abandoned them in favor of funding his war erases most of the value of his social agenda - a war he conspired to start, lied to the people about on a constant basis, and directly acknowledged in recordings that he would be impeached if he told the truth and ended it.
LBJ had some grandiose vision of America as a flourishing Empire with himself as a benevolent dictator or king, citizens living in equality and luxury, and the glorious military benevolently lording it over far-flung territories as a bulwark against the Soviet hordes. It wasn't a bad fantasy, as far as the sweep of history goes, but it just wasn't practical - especially in light of a rapidly evolving American society whose values began to diverge from Johnson's core assumptions. The kids were not on board with dying just to feed the economics of the military-industrial complex, the Domino Theory was increasingly seen as meretricious bunk with no geopolitical basis, many black activists were becoming radicalized rather than assuaged by gains made within the system, and people were tired of living under the threat of nuclear armageddon. Johnson could never understand these sorts of motivations, because he was a weaver of spiderwebs - a Byzantine politician in a situation that was, ironically, becoming too simple for him to understand.
Although we can justly laud his Civil Rights work - something he didn't have to do by any standard of realpolitik - Johnson was, more fundamentally, one who thought a big, simple problem could be solved by turning it into a large number of far more complex problems. Hence the Domino Theory - stop Soviet expansion by militarily intervening in every country along the border of its influence - and also the limited, nitpicking way in which the Vietnam War was conducted, parsing out every tactical targeting decision for geopolitical ramifications. It created the illusion of control on his part and that of his advisors while the reality on the ground remain hellish and chaotic. As per his nature, the simple answer completely eluded him: Don't send troops to Vietnam. We weren't attacked by Vietnam, the division of the country was almost entirely Diem's creation because he refused to accept the popularity of Ho Chi Minh, and there would have been opportunities to divide the Communist bloc in Asia if we had solicited involvement with Hanoi due to its distrust of China.
But Johnson saw the war as part of a machine that needed feeding, in the same way as he saw his social programs - it was all just greasing the wheels of Leviathan. Frankly, Johnson wanted war - it was part of his Texas political worldview, and he saw the military's role in society in terms that are more properly disposed to fascism than the army of a republic. He saw it as a service to the nation to make things up in order to justify deploying troops to Southeast Asia. So I'll admit that Johnson is one of the more complicated presidencies to judge, but I can't possibly call his a great one, and despite its surviving successes (e.g., Civil Rights, Medicare), I hesitate to call it a good one because of all the traumas it avoidably inflicted on this country for its own petty reasons.
Then we have Kennedy, who was basically a conservative with some populist trappings because of his youth and minority religion. He made a sport out of Red Baiting, purging media and academia of leftists, demagoguing various real or imagined armament "gaps" where the Soviets had allegedly surpassed us, instituted double-digit cuts in upper income and corporate taxes, appointed his brother Attorney General, spied on Civil Rights leaders with impunity, and let the CIA run wild in Cuba. Of course, he seemed to evolve into a liberal in the latter part of his presidency, coming more fully on board with Civil Rights, deploying the National Guard to enforce desegregation (Ike had already done so on a limited basis), and famously bringing the world through the Cuban Missile Crisis intact, but we usually ignore the extent to which his earlier attitudes played a role in creating the conditions for that crisis. We forget, in the glory of his "Berliner" speech, how much his own actions had stoked Cold War animosity and paranoia rather than helping to relieve them. Kennedy, more than any other US President, was responsible for bringing the world to the brink of nuclear annihilation, and yet it's usually he who gets credit for bringing the world back from that brink.
Furthermore, it was his slate of elite academic wonks who had architected the economics of the Vietnam War long before Lyndon Johnson became President - it was they who came up with the "Domino Theory," and invented all sorts of elaborate nonsense to explain how perpetual war would be a good idea for the American economy, the basis of LBJ's "Guns and Butter" mentality. They decided the ideal condition would be to bring the world right to the edge of total annihilation, then stop just short and continually feed a limited conventional conflict whose main objective is its own continuation rather than any kind of victory.
Kennedy was a dangerously inexperienced and underqualified Boy King who won election by attacking Nixon from the right and buying votes through his father's Mafia friends. The whole world was quite fortunate to have him in office at that time rather than Nixon, but we still cannot overlook the absolute facts of his character and administration. Although later he became more progressive (when he discovered, to his unfeigned astonishment, that America was not populated by Ivy League prep school alumni), and as a result his assassination took on the aura of liberal martyrdom, his administration was the origin of an incredible number of problems that would explode later in history: His was the first round of tax cuts benefiting the wealthy; the first politically-motivated military buildup of the modern era; the perpetuation of nuclear ICBMs; the economization of perpetual war; the founding of the School of the Americas as a base for training puppet dictators in the arts of oppression; etc. etc. He was more of an intriguing, multi-faceted character who landed right at the crux of massive happenings on the global stage than he was a great President.
Truman and FDR both presided over simpler and more trusting countries, and their power far exceeded that of a President today even while their level of accountability was much lower. This runs contrary to the ancestor-worshiping fantasies so many people find so comforting, imagining an America that was somehow freer, more liberal, and more progressive when black people couldn't go anywhere without hard stares, restaurants wouldn't serve Jews, women's only roles in society were as baby factories, and average people were expected to wear a coat and tie to get a haircut. The fact is that, although life was generally slower and more bucolic because most people lived a more rural lifestyle, it was harder - even with house calls by a local doctor, people didn't have the kind of health care that a person with no insurance has today by going to a hospital. Things are better than they were - we just feel the stress more acutely because they happen faster and involve more details.
And in terms of the Presidency, it was not some rustic, egalitarian institution where the public could just stop by and say hello - Presidents saw people during elections or when they needed to drum up support for something, and in between those times they basically didn't exist. That's what made FDR's fireside chats so radical - radio broadcasts he made directly to the American people, on average, once every four months. President Obama is practically in constant communication with the American people compared to FDR - compared, in fact, to Bill Clinton, the last President who made any effort whatsoever to communicate with the public (whereas Herr Bush just relaxed out in his Texas dacha while his Inner Circle ruled the regime).
Basically, people trusted Presidents a lot more, and Presidents did a lot more hinky shit with that trust as a result - the sheer size of the "insider" world was much bigger because it had so much less scrutiny. Corruption in the 1930s, '40s, and '50s didn't mean some elaborate framework of media narrative and image fueled by corporate financing - it meant a guy with a suitcase full of cash walked into your office and said they would pay you $50,000 to vote for the bill. It was common enough in Congress, so it was a pervasive fact that Presidents also had to deal with in getting their own agendas passed - they had to Play Ball, and it was a lot harder version of Ball than the one played today, even if it was easier to dispense with when the situation called for seriousness.
But, see, even the corrupt kept up appearances. They had to pretend to actually serve the country, and every once in a while, they would be put on the spot and have to set aside their agenda in order to keep their business going the other 364 days of the year. Roosevelt and Truman could count on that, and count on a public that would throw anyone out of Congress who failed to observe that minimum adherence to public trust. They had a lot to work with, regardless of how staggering the challenges before them. President Obama, meanwhile, is basically a lone voice in the wilderness of a government that no longer even feels the need to pretend it has something to do with the United States of America. Throughout Congress and the Executive bureaucracy are people who look at themselves as just another form of entrepreneur, and are surrounded by so many likeminded people that they're almost never called upon to put in their Bare Minimum for the country. They can hold us all hostage with impunity, and not even pretend to be doing anything else. They can commit outright treason in full view of the cameras, and the people on the other end will praise them for it or portray it as a legitimate difference of opinion.
This is the environment in which Barack Obama volunteered to lead America, and somehow he has still managed to achieve remarkable results. Somehow the Iraq War has still been ended, Iran has not been invaded despite a decade of saber-rattling by blowhards, we helped liberate Libya from the air and concluded our involvement with the thanks and gratitude of the Libyan people, killed Osama Bin Laden who had eluded us for a decade, brought healthcare to thirty million more Americans than had it before, poured forty billion dollars into rebuilding the economy, founded the ARPA-E program to push the envelope of energy technology, opened the military to gays and lesbians, got two liberal Supreme Court justices confirmed (and both women at that), preempted several right-wing terrorist militia plots to attack the US, rescued the American auto industry (saving millions of jobs), weekly online presidential addresses...the list just goes on and on of things this President has accomplished basically without the help of a halfway decent Congress or the general support of an informed public.
Barack Obama is a shockingly great President. Regardless of their group politics and his never have been in the military, soldiers strongly respect him; despite their distrust of his progressive fiscal outlook, businessmen generally respect him; despite his race, accentless English, and aristocratic intellectualism, he nonetheless manages to command an unusual level of respect in the South and Midwest, in areas that are full of wingnuts, and is fearless about visiting them and engaging with the people of those regions; and wherever he goes in the world, he is treated like a rock star because he remains a symbol of America's promise, and an eloquent leader who speaks universal truths while acknowledging universal realities in action.
There is no one I can name whom I would rather have in the White House at this time in American history, and no contemporary figure in politics who I think would do even a remotely comparable let alone superior job. Everyone else would, as far as I can tell, either be a by-the-numbers political hack, a helpless Carter archetype making plaintive appeals and pedantic fiats his subordinates ignore, or an impotent, raging Naderite banging his shoe on the table when moral authority alone fails to cause his agenda to magically succeed. Instead we have this guy, who has the befuddling habit of harvesting useful progress from even the most desolate political wastelands. Obama's values are the same as mine, his perceptions seem to track or even exceed mine, and I consider him my intellectual superior. I find his Presidency educational rather than galling or remedial, and that is what leadership should be. It's supposed to be a stronger-than-average example of what is good in a country, and I can say without reservation Barack Obama is definitely that: He exhibits the best qualities of what an American of good nature strives to be, and only truly low individuals would resent that. So, basically...FOUR MORE YEARS!
8:25 AM PT: Honestly, I hadn't intended for this to become a pie fight. Given my experience, I should have known better, but most of the area of contention seems to be the title, so let me put it this way: Insofar as it is legitimate to hold any President as "best," despite the circumstances of presidencies differing so widely, I consider it equally legitimate to say that Barack Obama is best as it would be to say it of Lincoln, Washington, or FDR. That isn't to belittle any one of them, just to place them in the same league and say that I consider Obama a legitimate candidate for best. Because, seriously, you can't really judge a President with any certainty unless you could have them all preside over each other's circumstances and see how they do. Maybe James K. Polk would have been a Great Leader in 1968, maybe FDR would be dogshit in the 1990s, who knows? The best we can do is judge on personal qualities and how they respond to what comes their way.
2:41 PM PT: Ugh, why do I bother telling truths that I know will cause the skeeviest creepy-crawlies to skitter out of the woodwark and start shitting all over everything? Hold out your hand in friendship, and they take it as an invitation to wipe their asses with it. What is wrong with some people?