Last month’s Supreme Court oral argument in National Labor Relations Board v. Noel Canning brought new attention to a recurring problem with the Obama administration. Despite his training as a former constitutional law lecturer, President Barack Obama continues to push dubious legal theories that fail to persuade even the most liberal justices to vote in his favor.

At issue in Noel Canning was the president’s use of the recess appointment power in January 2012 to add three new members to the National Labor Relations Board, a maneuver that occurred not when the Senate was in recess, but when Senate Republicans were instead holding pro forma sessions for the very purpose of denying the president his chance to make such appointments.

“I can’t find anything that says the purpose of this clause has anything at all to do with political fights between Congress and the President,” declared Clinton-appointee Justice Stephen Breyer, who was then grilling Solicitor General Donald Verrilli about Obama’s broad claim of executive authority. “Where is it in the history of this clause, in its origination, that it has as a purpose to allow the President to try to overcome political disagreement?”

Obama-appointee Justice Elena Kagan voiced similar concerns. “General, would you agree that this clause now is not mostly used to deal with emergencies arising from congressional absence?” Isn’t it true, Kagan continued, that the clause is now used primarily to deal “with congressional intransigence, with a Congress that simply does not want to approve appointments that the President thinks ought to be approved?” As Chief Justice John Roberts later summarized, the Senate “has an absolute right not to confirm nominees that the President submits.”

Judging by the oral argument, the White House may end up losing the case by a lopsided margin. And if it does, it won’t be the first time. In recent years, the Obama administration has suffered a string of embarrassing defeats at the Supreme Court, losing unanimously on issues ranging from warrantless GPS tracking to the free exercise of religion. As we await the outcome in Noel Canning, here are Obama’s biggest constitutional flops to date.

United States v. Jones (2012)

The Fourth Amendment protects “the right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures.” Yet that textual command did not stop the White House from arguing that law enforcement officials should be allowed to attach a GPS tracking device to a car without first obtaining a warrant. “If you win this case,” Justice Stephen Breyer said to Deputy Solicitor General Michael Dreeben during the November 2011 oral argument in United States v. Jones, "there is nothing to prevent the police or the government from monitoring 24 hours a day the public movement of every citizen of the United States.” (No, he wasn’t talking about the NSA.)

Although the Court divided in its reasoning, all nine justices rejected the Obama administration’s extreme position. “It is important to be clear about what occurred in this case,” declared the majority opinion of Justice Antonin Scalia. “The Government physically occupied private property for the purpose of obtaining information. We have no doubt that such a physical intrusion would have been considered a ‘search’ within the meaning of the Fourth Amendment when it was adopted.”

Arkansas Game & Fish Commission v. United States (2012)

According to the Takings Clause of the Fifth Amendment, if the government takes your property for a public use, it must pay you just compensation. Yet in Arkansas Game & Fish Commission v. United States, the Obama administration claimed that a series of destructive recurring floods induced by the U.S. Army Corps of Engineers did not count as a taking because the flood waters ultimately receded. In fact, the government argued, “temporary” flooding induced by the government should never qualify as a taking of property and therefore the Fifth Amendment should never apply in such cases. Writing for a 8-0 majority (with Justice Kagan recused), Justice Ruth Bader Ginsburg rejected the White House’s theory of the case. “No decision of this Court authorizes a blanket temporary-flooding exception to our Takings Clause jurisprudence, and we decline to create such an exception in this case,” Ginsburg held.

As for the government’s related argument that a decision in favor of the property-holders would hamstring the efforts of future officials, Ginsburg shot back:

Time and again in Takings Clause cases, the Court has heard the prophecy that recognizing a just compensation claim would unduly impede the government’s ability to act in the public interest. We have rejected this argument when deployed to urge blanket exemptions from the Fifth Amendment’s instruction.

Hosanna-Tabor Evangelical Lutheran Church and School v. Equal Employment Opportunity Commission (2012)

The First Amendment prevents the government from “prohibiting the free exercise” of religion. Yet in Hosanna-Tabor Evangelical Lutheran Church and School v. Equal Employment Opportunity Commission, the White House maintained that the Free Exercise Clause did not protect a parochial school from facing an anti-discrimination suit over its decision to fire a teacher whose duties included both secular and religious instruction. In the words of Cato Institute legal scholar Walter Olson, “The Obama administration had taken the disturbing position that there should be no ministerial exception at all to stand between churches and the full panoply of official employment regulation.”

The Supreme Court repudiated the White House’s approach. In a 9-0 opinion authored by Chief Justice John Roberts, the Court declared: “By imposing an unwanted minister, the state infringes the Free Exercise Clause, which protects a religious group’s right to shape its own faith and mission through its appointments.”

Sackett v. Environmental Protection Agency (2012)

At issue in Sackett v. Environmental Protection Agency was the EPA’s practice of issuing so-called administrative compliance orders. In essence, these were government commands handed down to property owners that were not subject to judicial review by the federal courts. In other words, the constitutional guarantee of due process did not come into play when the EPA took this particular form of action against the citizenry. According to the federal government, “a rule that broadly authorized immediate judicial review of such agency communications would ultimately disserve the interests of both the government and regulated parties, by discouraging interactive processes that can obviate the need for judicial action.”

The Supreme Court took a different view. “There is no reason to think that the Clean Water Act was uniquely designed to enable the strong-arming of regulated parties into ‘voluntary compliance’ without the opportunity for judicial review—even judicial review of the question whether the regulated party is within the EPA’s jurisdiction,” the Court ruled. The Obama administration lost the case 9-0.