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I believe I have it all figured out. Why Curtis seemingly cannot get elected to anything in spite of his qualifcations and friendly personality.

It’s that Red Beret.
As long as Curtis insists on always wearing that beret, the average New Yorker won’t be able to see him as anyone other than the leader of the Guardian Angels. This is a great group, but their tactics may seem overly confrontational, too ‘Tough Love’ like for some.
Also, some may consider the concept of Guardian Angels to be passe and a part of the distant past. Curt needs to update his image to appeal to younger New Yorkers.

I said the same thing when Kid Rock was pretending to ‘run’ for office some years ago. Not that i ever took him seriously. A lot of well meaning folks did though.
Kid Rock kept a hat on his head throughout the entire ‘campaign’, never once breaking character.

I don't want to say it, but I often think Curtis wears the beret because he's a hustler and know, in the end, he will ALWAYS have the Angels. I don't think he's faking this run...I think he's all-in. Buuut, I also think he is hedging his bets and building his brand while campaigning.

You may be right. In fact you probably are right. But I doubt the beret will go away.