I think Obama's single biggest flaw so far has been that he has tried too hard to compromise with the right who was not looking for compromise at all. Hopefully, the rights attitude will now change as they can try to take some credit for things passed but previously the right would just say no to everything. The compromises resulted in watered down legislation (for example health care reform) that the right still came out entirely against. He should have been a stronger president and implemented good legislation and said to hell with the right since that is what the public viewed he did anyway thanks to brilliant marketing by the right.
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