|Bold? Yes. Fortunate? Who knows.|
We like to think that “Fortune favors the bold”, but thankfully that’s not true at all. If being “bold” was always a good thing then this would be a great saying, but the boldest people don’t always have goodness in mind. To be bold is not intrinsically a positive thing. Being bold means to break the rules in the face of danger.
Lee Harvey Oswald was pretty damn bold to do what he did to JFK, but did fortune favor him? He was successful in his bold act, but then Jack Ruby showed up so I’m not sure that counted as being fortunate. Jack Ruby did something pretty bold. Did fortune favor him? Not really. And for a positive example, JFK was extremely bold, but fortune did not favor him on November 22, 1963. I think a better saying would be “Fortune favors the bold up to a certain point.” Because after that certain point you’re almost always screwed. I think that’s important to note. If I was going to be bold I would want to know about the whole “having everything go horribly wrong toward the end” part. Knowing that might make being unbold seem a lot more attractive and “fortunate”.