Before we can discuss whether we should give aid to those under a dictatorship, we must examine why we give aid in the first place. We give humanitarian aid because we, with means, have a moral obligation to ensure that others have access to essential necessities. This obligation comes from our personal ethical responsibility to be minimally good people and alleviate the most extreme human suffering as much as is realistically possible. This obligation isn’t based on strategic goals, it isn’t based on spreading democracy and it isn’t based on national security — it’s based on our moral duty to our fellow humans, and this doesn’t depend on who happens to lead their country.
This doesn’t mean giving humanitarian aid to dictatorships can’t come with strategic benefits. Providing this aid opens the door to normal diplomatic relations. Not normal in the sense that we approve of their behaviors or even recognize them as a legitimate government. I mean normal in terms of meeting on a regular basis, establishing ties and learning how to communicate. As any good game theorist knows, when two players continuously come in contact, have played together before and will play together again, the nature of the decision-making process changes. There is room to build trust, and there is the question of future risks and benefits. This means when the big issues are on the table, there is a framework within which to negotiate and hold each other accountable.
Furthermore, the United States gains the ability to pressure a country’s leadership when that country’s people are dependent on U.S. aid. To be sure, this is quite worrisome, but when the other option is an oppressive dictatorship, I’ll place my bets with the United States. And, most importantly, the central point remains: We as moral individuals, acting collectively through our government, have a duty to aid those in extreme suffering. If a byproduct of this is that a dictator gets richer, so be it. And when additional geo-strategic benefits come along with fulfilling our ethical obligations, all the better.