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From a truly progressive point of view, the Obama Presidency has been a failure as most of his policies have, at best, pulled America back to the Clinton years. The 1990′s saw welfare reform, the repeal of Glass Steagal, and the onslaught of neoliberalism at an unprecedented scale. While Obama promised a great deal of change before being elected, he got into office and immediately moderated his rhetoric and did not fight for progressive policy he had advocated.
However, I think you can subscribe to the idea that President Obama has done everything and more that his old Professor accuses him of, and is also the greatest force for progressive politics in America today. Not an easy task, but bear with me.
Every President elected to office in the United States automatically becomes a criminal. They are running a government responsible for decimating the Native American population, enslaving African Americans and then denying them their civil rights, going to war in Vietnam, much of Latin America, Iraq, Afghanistan and many other largely defenseless countries, economically strangling much of the third world (and the American poor) through punitive economic measures, destroying the environment through subsidizing the oil industry and refusing to adhere to carbon emission reduction agreements, enabling the insurance industry to deny people health care, etc etc etc.
To entertain the notion that a President could change all this in 4-8 years is simply ridiculous, particularly given the fact that the structure of the US government is designed to make change extremely difficult.