Describing Obama: "the constitutional lawyer in the White House" The question that this brings to mind is whether Obama agrees with our constitution's precepts. Wouldn't a constitutional lawyer be the perfect person to circumvent or destroy its intent? In much the same way a person that understands the internal workings of a lock is the best one to pick it?
A perfect example is the recent case in Jones. Is it unconstitutional because putting a GPS tracker in a car enables 24/7 surveillance, or because it requires the police to physically trespass on the car to place the tracker?
The protection of "privacy" in the constitution has been extended to reach things birth control and abortion based on the "penumbras" of the rights that are actually in the text. This is fuzzy ground! You can believe that those penumbras exist yet still not believe they cover recording information people put out into the public internet.
In short, its not so much that Obama is well-placed to know how to work around the Constitution, its that he knows that digital privacy is on unsure Constitutional footing in the first place and is positioned to take advantage of where the lines are drawn.