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The Obama team made 2 major miscalculations; the first was that they underated the severity of the recession, they didn't think they need something huge, that the economy would bounce back like it always does, boy, were they wrong. The second was that they thought they would be able to come back and do a second stimulus, not realizing that there was no rationality left in the Republican party, they were perfectly willing to let the economy collapse in order for them to get elected and win back majorities in both houses.
Ezra Klein goes into more detail, here's an excerpt:
Ten percent unemployment and a terrible recession ended up discrediting the people trying to do more for the economy, as their previous intervention was deemed a failure. That, in turn, empowered the people attempting to do less for the economy. So rather than a modestly sized stimulus leaving the door open for more stimulus if needed, its modest size was used to discredit the idea of more stimulus when it became needed.
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