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Paying Ransoms and Presidential Enforcement Discretion
Michael Ramsey

According to CNN

The payment of ransoms to terror groups like ISIS and al Qaeda has long been tolerated, though it is technically illegal. The administration has looked the other way when families of Americans held overseas have paid ransoms.

On Wednesday, the White House will explicitly indicate that families should not fear criminal prosecution if they choose to make ransom payments. The new directive will not include a formal change to existing laws. But administration officials will state publicly, for the first time, that ransom payments will be tolerated.

This strikes me as a much better test of executive enforcement discretion than the immigration non-enforcement debate, as it's not complicated by arguable changes in legal status, conferral of benefits, etc.  As I understand it, there's a law against aiding terrorists, which is violated by (among other things) paying ransoms to terrorists; the President is now declaring categorically that as to a specified class (families of hostages paying ransoms) the law will not be enforced, I assume principally for policy reasons.  As the CNN story notes "[t]he new directive will not include a formal change to existing laws" [well, that's a relief], but the families will be assured (in a non-binding way) of non-prosecution.

Is this within the President's constitutional power?  Some of the arguments raised in the immigration non-enforcement debate seem to suggest it is: it declares (a) in advance (b) a specified category of non-enforcement, (c) mainly for policy reasons.  If the immigration non-enforcement policy is unconstitutional for these reasons, the ransom non-enforcement policy should be as well.

But I think the hostage non-enforcement policy is within the President's power.  He is not dispensing with an entire law, but only mitigating the harsh and possibly unintended effect of a law in a particular set of circumstances.  He can argue that he is "faithfully execut[ing]" the law because (in his view) Congress would not want it enforced against this group (if Congress had thought about it).  And more fundamentally this is part of the check the executive power provides on the power of Congress.  

As Madison quoted Montesquieu in Federalist 47, "When the legislative and executive powers are united in the same person or body, there can be no liberty, because apprehensions may arise lest the same monarch or senate should enact tyrannical laws to execute them in a tyrannical manner."  That is, separating the enactment and the execution preserves liberty because (among other things) the body with execution power can mitigate unjust laws.  But this check works only if the executive authority has an independent power to assess the justness of a law as applied to particular circumstances.  And I see no reason why this check can't be applied in advance by an announced policy as to a designated class.

So in this case, I would argue, if the President concludes it's unjust to enforce laws prohibiting support of terrorism against families negotiating for the return of their loved ones, then that is part of the Madisonian/Montesquieu-ian liberty-protecting separation of powers.

(On the merits, I think allowing ransom to be paid to terrorists is a terrible idea, but that's not the point).