1. Perhaps to some extent, but it seems to me that the main purpose of this speech is to make an analogy between the Cold War and the War on Terror. This seems obvious in many ways throughout this speech, but this phrase really struck me:
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. . .an enemy "animated by a new fanatic faith" and determined to impose its ideology on the entire world.
There are several places in this speech where it seems as if a comparison is being made between Truman's Cold War policies and the War in Iraq.
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The Korean War saw many setbacks, and missteps and terrible losses. More than 54,000 Americans gave their lives in Korea. Yet, in the end, communist forces were pushed back to the 38th Parallel -- and the freedom of South Korea was secure.
(An admission of the cost in human lives of the War in Iraq, and a prediction that all will be for the best.)
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The Marshall Plan cost about $100 billion in today's dollars, and it helped to save Western Europe from Soviet tyranny, and led to the emergence of democratic allies that remain indispensable to the cause of peace today.
(An admission of the cost in dollars of the War on Terror, and a prediction that it will be worth it.)
It's worth noting that this speech deals only with Truman's foreign policy.
2 and 3. Their circumstances are vastly different. Truman was thrust unexpectedly into the White House by the death of FDR, after having been selected as Vice President only as a result of internal politics within the Democratic Party.
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In 1944, Hannegan was Democratic National Chairman. Roosevelt wanted to replace Henry Wallace as Vice President because he was considered too liberal. James F. Byrnes of South Carolina was initially favored, but as a segregationist he was considered too conservative. Hannegan offered Truman in what was dubbed the "Missouri Compromise" at the 1944 Democratic National Convention in Chicago.
Bush has been groomed for the Presidency.
Another important difference in circumstances is that Truman faced a Congress dominated by the opposing party, while Bush has both the House and the Senate under GOP control.
As far as character goes, that's more subjective. They both seem to have been firm/stubborn (pick one) but that's almost mandatory for the Chief Executive. Truman seems to have been more down-to-earth, more salty in character. Although Bush is not as obviously patrician in character as his father, his "I'm just a Texas cowboy" routine has never been entirely convincing to me.
Not much was expected of Harry S Truman*. He has since generally been ranked by scholars as one of the "top ten" Presidents.
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These standings vary, though three Presidents—in chronological order, George Washington, Abraham Lincoln, and Franklin D. Roosevelt—always are ranked at the top of the known lists. Normally ranking just below those three are Presidents Thomas Jefferson, Theodore Roosevelt, and Woodrow Wilson. The remaining "top 10" ranks are often rounded out by Andrew Jackson, Harry S. Truman, Dwight D. Eisenhower and James K. Polk. In recent polls, James Madison, James Monroe and Ronald Reagan have sometimes been ranked in the top 10.
It is too early to discuss a ranking for the current President, but he seems unlikely to reach this level of respect by future historians.
4. I don't think this speech will have much effect one way or the other.
*I prefer to list Truman's middle initial, which does not stand for anything, without a period. In this respect, I find myself nearly alone.
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He once joked that the S was a name, not an initial, and it should not have a period, but official documents and his presidential library all use a period. Furthermore, the Harry S. Truman Library has numerous examples of the signature written at various times throughout Truman's lifetime where his own use of a period after the "S" is very obvious.