One of our newspaper columnists used the word chumbolone, which I found in Doubled-Tongued Dictionary to be a slang to mean "idiot." It seems to have an Italian etymology. Have you seen it used? Neither Shu nor I have, though our son says he hears it all the time. It isn't in Onelook or the OED.
Calabrese said he met with several tough guys, including Outfit loan shark and former Chicago Police Officer Anthony "Twan" Doyle. Twan was convicted in Family Secrets for passing key information on an Outfit murder to Calabrese's brother, Frank Calabrese Sr., while the FBI was recording their conversations.
(Ironically, Twan invented the term "chumbolone," which he insisted means stupid idiot.)
It doesn't look like an Italian word, the letter combination ch is pronounced /k/ and only appears in front of the vowels e and i, e.g., che 'who, whom, which' /ke/, chi 'whoever' /ki/. I guess the u is being pronounced as a schwa. The -one ending is an augmentative suffix in Italian (and some related endings in other Romance languages) and usually has pejorative connotations.
A ciambella is a kind of ring cake, so I guess ciambellone might be some kind of term for doughnut, the favorite food of law enforcement in Chicago and environs.
I hadn't gone through all the Google sites, but, you're right, it seems to come from Chicago and especially from that chombolone, John Kass. (I hold my nose every time I read his factless, but opinionated, articles.)
Don't take this as gospel, since I am not Italian. I asked my wife, who is Italian, if she had ever heard of the word. She hadn't. However, she wondered if it was a corruption of strombolone, which (aqccording to her limited Italian language skills) means "oafish" or "clumsy." Now THAT'S Chicago!
