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The biggest stain on Obama's legacy would have been whether or not he contributed, caused, or was a victim of DC dysfunction during his term. History would have argued whether or not he could have done more to reach across the aisle and bridge differences. After all, that what he promised.
Boehner stepping down from the speakership is the nail in the coffin for that argument. Nothing short of Obama converting to a Republican would have solved the gridlock. If Republicans can't even get on the same page about what they want as a party, how is a Democrat supposed to work with them? If Republicans can't even work with THEIR leader, what realistic expectation is there for them to work for the leader of the opposing party.
Not only is Boehner's ouster going to rightfully repaint the entire nature of the dysfunction and plant it squarely on the shoulders of a Republican party that was so toxic, they couldn't even keep their own house in order, it's going to repaint Obama as a much shrewder and politically savvy President than he actually is and was.
One the one hand, you have a growing Republican control of Congress and their legacy so far is having tossed two of their top leaders from their perches and fumbling their way towards a gov't shutdown.
Meanwhile, Obama has gotten healthcare reform, Iranian peace deals, populist legislation across the country to increase wages, LGBT civil right gains, American resurgence in energy production AND leading the world in new green technology, jobs, corporate profits... All this happened when the opposition couldn't keep their stray cats together long enough to get a headcount.