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The timeline of Obamacare delays arbitrarily imposed by the Obama administration.
Practically all of these are illegal, as the law does not give the president the power to make these changes. Also, note the wide gap from July 2, 2013 to November 27, 2013, when no delay orders were issued. It was during this time period that Obama and the Democrats in Congress were refusing to negotiate with Republicans about a variety of proposed Republican delays to the law. The result of this refusal was the shutdown of the government in October. Had the Democrats been willing to negotiate then, these delays would at least have been legal, and there would not have been a shutdown.