The root meaning of “chutzpah” is “to be insolent or impudent,” and “chutzpah” has come into Yiddish with the same meaning as it has in Hebrew: “impudence, insolence, nerve,” to quote Uriel Weinreich’s Modern English-Yiddish Yiddish-English Dictionary. There’s nothing good about chutzpah in Yiddish; it’s an unambiguously negative quality characterized by a disregard for manners, social conventions, and the feelings and opinions of others.
The chutzpahnik’s self-regard and sense of entitlement are so total that he’s unable to see that other people are just as real as he is. (If he’s a she, the chutzpahnik is called a chutzpahnitseh.) Chutzpah comes to your house for dinner and takes a dump in your potted plant; if it goes to its best friend’s funeral and then propositions the bereaved spouse during the shiva, it’s only because there was no chance to do so at the graveside.