From Walter Olson at Overlawyered.com:

Why does Obama keep losing in the Supreme Court?

June 12, 2013

And why are many of the decisions against him unanimous? Ilya Shapiro has some ideas, and an update at Cato. And from Ramesh Ponnuru: “Obama’s Dangerous Contempt for the Rule of Law.”

The answer briefly is Federal overreaching—neither Obama nor his subordinates believes that there are any limits to Federal power, and the Supreme Court keeps saying there are.

Ilya Shapiro, an adjunct professor at the George Washington University Law School,writes

In cases before the Supreme Court last year, President Barack Obama’s Justice Department relied on outlandish legal theories that pushed a constitutional interpretation of extreme federal power [Why Obama Keeps Losing at the Supreme Court, Bloomberg.com,  June 7, 2013.]

He has an interesting sidelight on the Arizona immigration case, in which Holder's Justice Department sued Arizona over SB1070:

Consider another major case from the 2011-12 term: Arizona v. U.S.

The conventional narrative is that the Supreme Court smacked down a perniciously anti-immigrant Arizona law that gave state police more power to enforce immigration laws. That interpretation simply isn’t correct. Only four sections of the law reached the Supreme Court — most of its provisions weren’t even challenged — and the U.S. won split decisions on three and unanimously lost the fourth.

Immigration Powers

The three splits involved complicated statutory interpretation regarding pre-emption of state law by federal law. In the ruling on the fourth, however,not a single justice accepted the government’s theory that mere federal enforcement priorities — as opposed to laws or regulations — trumped state law.

The government argued that discretionary decisions not to enforce certain federal laws overrode parallel state laws that enforced those same laws. The unanimous Supreme Court rejected that breathtaking claim of “pre-emption by executive whim.”

This was also VDARE.com's view of Arizona vs. U.S—see SCOTUS On Arizona’s SB 1070: A Victory…If Immigration Patriots Can Make It One, by Washington Watcher. I wonder if there's some way you could get the Administrative Amnesty to the Supreme Court?