I wonder, the way human brain works, is it common for there to be thoughts that are much better expressed with a short sentence full of ambiguous connotations, that by long and accurate explanations?

No, unless by "better" you mean "more entertaining/artistic". An ambiguous statement might feel more meaningful by tripping so many associations at once, but pretty much by definition it contains less information than a less ambiguous counterpart.

That said, a statement like "rationality is winning" can usefully summarize larger concepts, but only once it's been contextually disambiguated. It's useless on its own.