The easiest way to make a very academic sounding title is to use the following over-used format: "Some kind of quote": The basic subject of your paper. The quote could be a paraphrase. E.g., "Tightening the Knot of War: The Cuban Missile Crisis in Retrospective." (The knot of war references Khrushchev's famous letter to JFK, which, if you used this in the title, you should probably make reference to in the introduction of the paper, to guarantee the reader understands.) "Verbing the Noun: One thing, a second thing, and a third thing" is another very straightforward and perhaps overused approach. (I am guilty of all cliches myself, of course

These are "easy" formats and you'll notice in many academic history journals it is practically the "default" approach. It works fine for an undergraduate dissertation, too. It has the ring of professionalization and tradition (if, perhaps, cliche — but nobody will hold that against an undergraduate, because you learn how to do these things first by replicating the existing patterns). Just don't make it a play on a Dickens title, please ("A Tale of Two Somethings" is quite overdone).

But even having it just be a "ridiculously basic" question can be fine, as long as the dissertation itself is not "ridiculously basic." "The Cuban Missile Crisis: Who Won, Who Lost?" is a totally acceptable, straightforward title, and makes it look (to my eye) like you are concerned with the question, not trying to overly complicate things with academic finery. But you pick what best represents your aim here. Sometimes a good title will hint at your thesis, e.g., "The Cuban Missile Crisis: Beyond Winners and Losers", makes it clear that the author rejects the binary of a win/lose framing.