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Controversies were visited on each president that were unfortunate and might have been avoided. In this section, I will decide on which president had, comparatively, the lightest controversial issues. I will do this by assessing how things might have gone (good or ill), and trying to determine from that how damaging the problems were for the nation over time.
Controversies and Failures
One of the controversial issues with Roosevelt was the fact that he set a worrying precedent for taking vast amounts of executive power in times of crisis. No other president before him had been given so much power in order to fix the problems of the time. While it is debatable that this might have been avoided, it is arguable that he could have given greater portions of the responsibility and power to the legislative branch instead of pushing through executive orders in rapid succession. Much like Obama gave the healthcare project to the Senate to work out, Roosevelt might have given a number of projects and ideas for the Senate of the time to look over and then execute. If he had done this, he might have avoided issues of constitutionality and calmed fears of his wielding of executive power. Instead, he set a precedent for greater executive power that would be later abused by presidents such as Nixon and Bush Junior, for example.
This willingness to use power in his own interest directly led to his attempt to pack the Supreme Court in his favor. As far as I know, there has yet to be a comparable attempt of a naked grab for power among American presidents. In any case, he was roundly condemned for it and the two parties, who had previously been supporting everything Roosevelt did, joined together in opposing this attempt. However, despite the fact that this was definitely something Roosevelt shouldn't have done, I think it is excellent that another precedent was set here; the precedent that, even when executive power is at its maximum, the system of checks and balances still works. Roosevelt was miffed that he failed to manipulate the Supreme Court, but the united resistance made him back off for good.
Lastly, Roosevelt was responsible for the mass internment of Japanese into camps during World War II, conspicuously making minimal effort to do the same for Germans and Italians in America, whose populations were even greater. This was clearly racism in action, and it is hard to not look at this without disapproval. However, it is impossible to predict if anything would have happened if they had not been interned into camps. It is entirely possible that there were saboteurs and insurrectionists among the Japanese population; we don't really know for sure. When the decision was made, it seemed completely justified, and the interning of Japanese exclusively was simply indicative of the less tolerant times. Thus this is a more murky issue, and hard to decry altogether.
Truman authorized the use of the atomic bomb on Japan, which gives rise to heavy debate to this very day. At the time, support was almost universal in favor of dropping the bomb. The rationale was that this was a war, and that crippling the enemy so that more friendly soldiers would not have to die was perfectly acceptable. Today, those who argue against it point out that there was no certainty that the Japanese were going to resist at every step of the way, causing the further bloodbath of millions. Human nature would suggest that, similar to Germany's last days, people in Japan's government would see that fighting to the death was a poor decision, and steps would be taken to perhaps overthrow the Emperor or influence him in a way that would make surrender more palatable. Either way, it is difficult to know for sure.
Truman also brought America into the Korean War. His rationale at containing communism's spread was justified, but the crux of the matter was whether continuing on to win against North Korea (and Chinese forces in North Korea) might have perhaps ended the Cold War altogether. If Truman had decided to finish what he started in Korea instead of settling on the initial status quo of separation via the 38th parallel. Russia and China might have been far less willing to conflict with the United States in this scenario, as they would have seen a show of strength and no weakness whatsoever. Of course, on the other hand, trying to finish the conquest of North Korea might have resulted in nuclear war or World War III. Needless to say, settling on the initial bordering between Koreas after a long and costly war seemed to be a waste of lives and an altogether pointless affair. The only saving grace was that communism's expansion was successfully contained.
Finally, Truman failed to act in a meaningful way against the growing Red Scare, the threat of communism being everywhere within the United States that was fueled by the demagoguery of Senator McCarthy. Feeling that the movement would peter out by itself, Truman decided to ignore it, which was not a good decision. If he had acted decisively against it from the beginning, he might have saved future presidents a lot of trouble. As it was, McCarthyism and the Red Scare created an atmosphere of paranoia and terror among the American people and many of its politicians for decades to come, only heightening fears of nuclear annihilation.
The Final Winner
After long deliberation, I think that Roosevelt wins this one, and thus the presidential showdown, winning in two of the three categories. Of his controversies, only the boosting of executive power had negative ramifications for the future that we can see to this very day. His attempt to pack the Supreme Court was an extremely poor decision for the time, but in the end set a positive precedent. And the internship of Japanese was unclear as to if it was justified or not, and it was a one-time issue in an incredibly unique and tumultuous time.
By contrast, every one of Truman's controversies caused problems down the road that might have been averted. What would have happened if he hadn't of nuked Japan? A more peaceful world, perhaps? What if he had kept America in the Korean War until it had won instead of settling on the stalemate line? A potentially meeker Soviet Union and China? What if Truman had stamped down and taken action against the rumors and threats of prevalent communist spies? Americans less paranoid, more confident, and a Soviet Union robbed of its dark and fearful image?
Of course, any one of Truman's controversies might have got a whole lot worse if he had done something about them. There is no way of knowing for sure. But it is clear that his were significantly more problematic, had longer negative ramifications, and altogether had more positive possibilities if he had done something differently.
Thus does Roosevelt take the final prize.
It's been a fun ride, and I've enjoyed detailing the presidents' lives and gauging their strengths and weaknesses. In the end, I'm a little sad that Truman lost, though. Of the two, I think Truman is a far better person, and after reading his biography I can say that he makes an excellent role model and an inspirational figure who wouldn't step down and refused to compromise his morals. Of course, Roosevelt was the best and had unmatched political skill. But Truman remains the more attractive figure to me and, if one were to ask, I would recommend reading a biography of himself above reading a biography of Roosevelt. Roosevelt was very tightly controlled and enjoyed fostering a particular view of him, and thus there is less truly known about him. But Truman was far more enthralling and he was always honest, leading to more interesting and inspirational stories about him and his love for the common man.