So one of my professors old exams deals with a situation where a state creates a tax on all airline flights in and out of their state. Congress enacts a Bill3 months later encouraging states to enact such taxes (essentially giving the states permission to tax airline flights). 4 months later the President enters into an executive agreement with Canada agreeing that neither state will tax airline flights.
We then have to discuss the constitutionality of the tax at each interval.
I have that initially, it is unconstitutional because it is a violation of the dormant commerce clause. Then it is constitutional because Congress gives the states the powers to do so. I am having trouble with the last one because I am not sure if the President can enter into an executive agreement that deals with taxing, which is an enumerated power of Congress. If he can, then I would argue the executive agreement overrules any inconsistent state laws, but if he can't then it would not be a valid executive agreement.
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Executive agreements are perfect for a Youngstown Sheet & Tube analysis (the 3-part system in Justice Jackson's opinion). This involves questions like whether the President can enter into executive agreements about taxing, or whether this is Congress' sole domain. Here it seems that the president's actions fall into the third category, and thus the president's power is presumptively unconstitutional unless you can show that the president has sole authority to do what he did and that Congress can't constitutionally affect this power.
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Youngstown is obviously important for the reasons stated above. Even if the executive agreement carries the force of a treaty (not clear at all that it does), it might not be able to preempt the states from imposing a tax because it is not self-executing, and Congress has not passed legislation to bring it into force (Medellin). Moreover, even though the Court has acknowledged that the President has broad latitude to enter into executive agreements, and that those executive agreements preempt state law (Garamendi), that case might be distinguishable because the executive agreement at issue there was consistent with Congressional support for settlement of international claims.